Abstract
Metalloporphyrins and phthalocyanines have remarkable electrocatalytic properties, generally associated with the ring coordinated transition metal ion, which can be further improved based on supramolecular approach, by combination with suitable molecular ancillary groups. Among the possibilities, transition metal complexes such as ferrocene and ruthenium polypyridine complexes, as well as bisthiophene, dendrimers, and other macrocycles. For example, the electrochemical and photoinduced electron transfer properties of metalloporphyrin-dendrimer based systems (metalloporphyrin in dendrimer core, branches or periphery) are affected by dendrimer structure. The dendrimers at higher generations are globular structures providing many possibilities to arrange electroactive groups in different microenvironments giving rise to new properties and functionalities. Phenylazomethine dendrimers with a cobalt porphyrin core was applied for catalytic CO2 reduction in the presence of Lewis acid at relatively low overpotentials, due to the synergetic effect of the assembled metal ions and the porphyrin core involving a multielectron transfer process. That strategy has been extended by associating them with nanoparticles opening broad new perspectives in porphyrin and phthalocyanine chemistry. In fact, the combination with carbon, metals, sulfides, and oxides-based nanoparticles, as well as lamellar materials, is generating a whole new series of hybrid organic/inorganic nanomaterials with enhanced electrochemical, electrocatalytic, and photocatalytic properties. For example, porphyrin nanocomposites with lamellar materials such as vanadium pentoxide xerogels were explored as chemical vapor sensors. Ethinyl metalloporphyrin derivatives have been anchored to carbon nanotubes by electropolymerization, and the hybrid nanomaterial was shown to exhibit enhanced electroanalytic activity for tetraelectronic reduction of dioxygen. The electropolymerization of meso-tetra(4-sulfonatophenyl)porphyrinate manganese(III) in the presence of minute amounts of AgCl in alkaline solution was performed generating nanoflakes of MnTPPS decorated with MnO2 and silver nanoparticles, showing high electrocatalytic activity and sensitivity in hydrazine amperometric sensors. Also, porphyrins have been bond to carbon nanotubes, carbon nanohorns, graphene and graphene oxide, as well as fullerenes, generating interesting material for electrochemical and light-harvesting devices. The previous account (2006) was focused on the electrochemical modulation of electrocatalytic, as well as interaction and conduction properties, by electronic effects induced by ancillary groups, more specifically transition metal complexes. Now, a clear tendency of incorporating porphyrins and other macrocycles in nanosystems generating hybrid organic/inorganic nanomaterials is observed, widening the scope and perspectives in the porphyrin and phthalocyanine chemistry, as well as their electrochemical applications.
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References
Ishihara S, Labuta J, Van Rossom W, Ishikawa D, Minami K, Hill JP, Ariga K (2014) Porphyrin-based sensor nanoarchitectonics in diverse physical detection modes. Phys Chem Chem Phys 16(21):9713–9746
Torre G, Bottari G, Sekita M, Hausmann A, Guldi DM, Torres T (2013) A voyage into the synthesis and photophysics of homo- and heterobinuclear ensembles of phthalocyanines and porphyrins. Chem Soc Rev 42:8049–8105
Leznoff CC, Lever ABP (eds) (1997) Phthalocyanines, properties and applications, vol 4. Wiley, New York
Araki K, Toma HE (2006) Supramolecular porphyrins as electrocatalysts. In: Zagal J, Bedioui F, Dodelet JP (eds) N4-macrocyclic metal complexes. Springer, New York, pp 255–314
Araki K, Toma HE (2009) Supramolecular porphyrin model compounds for cytochrome p-450, cytochrome-c oxidase and photosynthetic systems. In: Merce ALR, Felcman J, Recio MAL (eds) Molecular and supramolecular bioinorganic chemistry: applications in medical sciences. Nova Science Publishers, New York, pp 83–136
Toma HE, Araki K (2009) Exploring the supramolecular coordination chemistry-based approach for nanotechnology. In: Karlin KD (ed) Progress in inorganic chemistry, vol 56. Wiley, Hoboken, pp 379–485
Balzani V, Bergamini G, Ceroni P (2008) From the photochemistry of coordination compounds to light-powered nanoscale devices and machines. Coord Chem Rev 252(23–24):2456–2469
Yamada Y, Okamoto M, Furukawa K, Kato T, Tanaka K (2012) Switchable intermolecular communication in a four-fold rotaxane. Angew Chem Int Ed 51(3):709–713
Yamada Y, Mihara N, Shibano S, Sugimoto K, Tanaka K (2013) Triply stacked heterogeneous array of porphyrins and phthalocyanine through stepwise formation of a fourfold rotaxane and an ionic complex. J Am Chem Soc 135(31):11505–11508
Hamer M, Tomba JP, Rezzano IN (2014) Optical properties and sensor applications of bimetallic nanostructures of porphyrins. Sens Actuators, B 193:121–127
Toma HE, Araki K (2000) Supramolecular assemblies of ruthenium complexes and porphyrins. Coord Chem Rev 196(1):307–329
Toma HE, Araki K, Alexiou ADP, Nikolaou S, Dovidauskas S (2001) Monomeric and extended oxo-centered triruthenium clusters. Coord Chem Rev 219:187–234
Araki K, Dovidauskas S, Winnischofer H, Alexiou ADP, Toma HE (2001) A new highly efficient tetra-electronic catalyst based on a cobalt porphyrin bound to four mu(3)-oxo-ruthenium acetate clusters. J Electroanal Chem 498(1–2):152–160
Araki K, Winnischofer H, Viana HEB, Toyama MM, Engelmann FM, Mayer I, Formiga ALB, Toma HE (2004) Enhanced electrochemical and electrocatalytic activity of a new supramolecular manganese-porphyrin species containing four bis(bipyridine)(aqua)ruthenium(II) complexes. J Electroanal Chem 562(2):145–152
Winnischofer H, Otake VY, Dovidauskas S, Nakamura M, Toma HE, Araki K (2004) Supramolecular tetracluster-cobalt porphyrin: a four-electron transfer catalyst for dioxygen reduction. Electrochim Acta 49(22–23):3711–3718
Dovidauskas S, Toma HE, Araki K, Sacco HC, Iamamoto Y (2000) (5,10,15,20-Tetra(4-pyridil)porphinato)manganes(III) acetate modified by four mu(3)-oxo-triruthenium acetate clusters: synthesis, characterization, electrochemical behavior and catalytic activity. Inorg Chim Acta 305(2):206–213
Nunes GS, Mayer I, Toma HE, Araki K (2005) Kinetics and mechanism of cyclohexane oxidation catalyzed by supramolecular manganese(III) porphyrins. J Catal 236(1):55–61
Nogueira AF, Formiga ALB, Winnischofer H, Nakamura M, Engelmann FM, Araki K, Toma HE (2004) Photoelectrochemical properties of supramolecular species containing porphyrin and ruthenium complexes on TiO2 films. Photochem Photobiol Sci 3(1):56–62
Nogueira AF, Furtado LFO, Formiga ALB, Nakamura M, Araki K, Toma HE (2004) Sensitization of TiO2 by supramolecules containing zinc porphyrins and ruthenium-polypyridyl complexes. Inorg Chem 43(2):396–398
Parussulo ALA, Iglesias BA, Toma HE, Araki K (2012) Sevenfold enhancement on porphyrin dye efficiency by coordination of ruthenium polypyridine complexes. Chem Commun 48(55):6939–6941
Araki K, Losco P, Engelmann FM, Winnischofer H, Toma HE (2001) Modulation of vectorial energy transfer in the tetrakis[tris(bipyridine)ruthenium(II)]porphyrinate zinc complex. J Photochem Photobiol A 142(1):25–30
Azevedo CMN, Araki K, Angnes L, Toma HE (1998) Electrostatically assembled films for improving the properties of tetraruthenated porphyrin modified electrodes. Electroanal 10(7):467–471
Mayer I, Nakamura M, Toma HE, Araki K (2006) Multielectronic redox and electrocatalytic supramolecular films based on a tetraruthenated iron porphyrin. Electrochim Acta 52(1):263–271
Martins PR, Popolim WD, Nagato LAF, Takemoto E, Araki K, Toma HE, Angnes L, Penteado MDVC (2011) Fast and reliable analyses of sulphite in fruit juices using a supramolecular amperometric detector encompassing in flow gas diffusion unit. Food Chem 127(1):249–255
Matsumoto MY, Toyama MM, Mayer I, Winnischofer H, Araki K, Toma HE (2009) Electronic conduction and electrocatalysis by supramolecular tetraruthenated copper porphyrazine films. J Braz Chem Soc 20:728–736
Dreyse PA, Isaacs MA, Iturriaga PE, Villagra DA, Aguirre MJ, Kubiak CP, Glover SD, Goeltz JC (2010) Electrochemical preparation of conductive films of tetrapyridylporphyrins coordinated to four [Ru(5-NO2-phen)2Cl]+ groups. J Electroanal Chem 648(2):98–104
Azevedo CMN, Araki K, Toma HE, Angnes L (1999) Determination of sulfur dioxide in wines by gas-diffusion flow injection analysis utilizing modified electrodes with electrostatically assembled films of tetraruthenated porphyrin. Anal Chim Acta 387(2):175–180
Winnischofer H, Formiga ALB, Nakamura M, Toma HE, Araki K, Nogueira AF (2005) Conduction and photoelectrochemical properties of monomeric and electropolymerized tetraruthenated porphyrin films. Photochem Photobiol Sci 4(4):359–366
Winnischofer H, Lima SD, Araki K, Toma HE (2003) Electrocatalytic activity of a new nanostructured polymeric tetraruthenated porphyrin film for nitrite detection. Anal Chim Acta 480(1):97–107
Dreyse P, Isaacs M, Calfumán K, Cáceres C, Aliaga A, Aguirre MJ, Villagra D (2011) Electrochemical reduction of nitrite at poly-[Ru(5-NO2-phen)2Cl] tetrapyridylporphyrin glassy carbon modified electrode. Electrochim Acta 56(14):5230–5237
Dreyse P, Quezada D, Honores J, Aguirre MJ, Mendoza L, Matsuhiro B, Villagra D, Isaacs M (2012) Determination of S(IV) oxoanions at Poly[Ru(5-NO2-Phen)2Cl] tetrapyridylporphyrin glassy carbon modified electrode. Electroanal 24(8):1709–1718
Calfumán K, Aguirre M, Villagra D, Yañez C, Arévalo C, Matsuhiro B, Mendoza L, Isaacs M (2010) Nafion/tetraruthenated porphyrin glassy carbon-modified electrode: characterization and voltammetric studies of sulfite oxidation in water–ethanol solutions. J Solid State Electrochem 14(6):1065–1072
Calfumán K, García M, Aguirre MJ, Matsuhiro B, Mendoza L, Isaacs M (2010) Electrochemical reduction of S(IV) compounds in water-ethanol solutions at nafion/tetraruthenated porphyrins glassy carbon modified electrodes. Electroanal 22(3):338–344
Naue JA, Toma SH, Bonacin JA, Araki K, Toma HE (2009) Probing the binding of tetraplatinum(pyridyl)porphyrin complexes to DNA by means of surface plasmon resonance. J Inorg Biochem 103(2):182–189
Marek D, Narra M, Schneider A, Swavey S (2006) Synthesis, characterization and electrode adsorption studies of porphyrins coordinated to ruthenium(II) polypyridyl complexes. Inorg Chim Acta 359(3):789–799
Vinyard DJ, Swavey S, Richter MM (2007) Photoluminescence and electrogenerated chemiluminescence of a bis(bipyridyl)ruthenium(II)–porphyrin complex. Inorg Chim Acta 360(5):1529–1534
Narra M, Elliott P, Swavey S (2006) Synthesis, characterization and DNA interactions of 5,15-(4-pyridyl)-10,20-(pentafluorophenyl)porphyrin coordinated to two [Ru(bipy)2Cl]+ groups. Inorg Chim Acta 359(7):2256–2262
Craver E, McCrate A, Nielsen M, Swavey S (2010) Tris-ruthenium(II)/copper(II) multimetallic porphyrin: synthesis, characterization, DNA binding and supercoiled DNA photocleavage studies.Inorg Chim Acta 363(2):453–456
García C, Ferraudi G, Lappin AG, Isaacs M (2012) Synthesis, spectral, electrochemical and flash photolysis studies of Fe(II), Ni(II) tetrapyridylporphyrins coordinated at the periphery with chromium(III) phenanthroline complexes. Inorg Chim Acta 386:73–82
Bucher C, Devillers CH, Moutet J-C, Royal G, Saint-Aman E (2009) Ferrocene-appended porphyrins: syntheses and properties. Coord Chem Rev 253(1–2):21–36
Fukuzumi S, Okamoto K, Gros CP, Guilard R (2004) Mechanism of four-electron reduction of dioxygen to water by ferrocene derivatives in the presence of perchloric acid in benzonitrile, catalyzed by cofacial dicobalt porphyrins. J Am Chem Soc 126(33):10441–10449
Mase K, Ohkubo K, Fukuzumi S (2013) Efficient two-electron reduction of dioxygen to hydrogen peroxide with one-electron reductants with a small overpotential catalyzed by a cobalt chlorin complex. J Am Chem Soc 135(7):2800–2808
Samanta S, Mittra K, Sengupta K, Chatterjee S, Dey A (2013) Second sphere control of redox catalysis: selective reduction of O2 to O2 − or H2O by an iron porphyrin catalyst. Inorg Chem 52(3):1443–1453
Das D, Lee Y-M, Ohkubo K, Nam W, Karlin KD, Fukuzumi S (2013) Acid-induced mechanism change and overpotential decrease in dioxygen reduction catalysis with a dinuclear copper complex. J Am Chem Soc 135(10):4018–4026
Das D, Lee Y-M, Ohkubo K, Nam W, Karlin KD, Fukuzumi S (2013) Temperature-independent catalytic two-electron reduction of dioxygen by ferrocenes with a copper(II) tris[2-(2-pyridyl)ethyl]amine catalyst in the presence of perchloric acid. J Am Chem Soc 135(7):2825–2834
Fukuzumi S, Kotani H, Lucas HR, Doi K, Suenobu T, Peterson RL, Karlin KD (2010) Mononuclear copper complex-catalyzed four-electron reduction of oxygen. J Am Chem Soc 132(20):6874–6875
Sun B, Ou Z, Meng D, Fang Y, Song Y, Zhu W, Solntsev PV, Nemykin VN, Kadish KM (2014) Electrochemistry and catalytic properties for dioxygen reduction using ferrocene-substituted cobalt porphyrins. Inorg Chem 53(16):8600–8609
Dammer SJ, Solntsev PV, Sabin JR, Nemykin VN (2013) Synthesis, characterization, and electron-transfer processes in indium ferrocenyl-containing porphyrins and their fullerene adducts. Inorg Chem 52(16):9496–9510
Vecchi A, Erickson NR, Sabin JR, Floris B, Conte V, Venanzi M, Galloni P, Nemykin VN (2015) Electronic properties of mono-substituted tetraferrocenyl porphyrins in solution and on a gold surface: assessment of the influencing factors for photoelectrochemical applications. Chem Eur J 21(1):269–279
Nemykin VN, Rohde GT, Barrett CD, Hadt RG, Bizzarri C, Galloni P, Floris B, Nowik I, Herber RH, Marrani AG, Zanoni R, Loim NM (2009) Electron-transfer processes in metal-free tetraferrocenylporphyrin. Understanding internal interactions to access mixed-valence states potentially useful for quantum cellular automata. J Am Chem Soc 131(41):14969–14978
Solntsev PV, Neisen BD, Sabin JR, Gerasimchuk NN, Nemykin VN (2011) Synthesis, characterization, X-ray structure, and mixed-valence states of trans -dichlorotin(IV)-5,10,15,20-tetraferrocenylporphyrin. J Porphyrins Phthalocyanines 15:612–621
Kalita D, Morisue M, Kobuke Y (2006) Synthesis and electrochemical properties of slipped-cofacial porphyrin dimers of ferrocene-functionalized Zn-imidazolyl-porphyrins as potential terminal electron donors in photosynthetic models. New J Chem 30(1):77–92
Formiga ALB, Nogueira AF, Araki K, Toma HE (2008) Contrasting photoelectrochemical behaviour of two isomeric supramolecular dyes based on meso-tetra(pyridyl)porphyrin incorporating four ([small mu ]3-oxo)-triruthenium(iii) clusters. New J Chem 32(7):1167–1174
Henderson J, Kubiak CP (2014) Photoinduced mixed valency in zinc porphyrin dimer of triruthenium cluster dyads. Inorg Chem 53(20):11298–11306
Lo P-C, Leng X, Ng DKP (2007) Hetero-arrays of porphyrins and phthalocyanines. Coord Chem Rev 251(17–20):2334–2353
Gatti T, Cavigli P, Zangrando E, Iengo E, Chiorboli C, Indelli MT (2013) Improving the efficiency of the photoinduced charge-separation process in a rhenium(I)–zinc porphyrin dyad by simple chemical functionalization. Inorg Chem 52(6):3190–3197
Gabrielsson A, Lindsay Smith JR, Perutz RN (2008) Remote site photosubstitution in metalloporphyrin-rhenium tricarbonylbipyridine assemblies: photo-reactions of molecules with very short lived excited states. Dalton Trans 32:4259–4269
Lachaud F, Jeandon C, Monari A, Assfeld X, Beley M, Ruppert R, Gros PC (2012) New dyads using (metallo)porphyrins as ancillary ligands in polypyridine ruthenium complexes. Synthesis and electronic properties. Dalton Trans 41(41):12865–12871
Murai M, Sugimoto M, Akita M (2013) Zinc-porphyrins functionalized with redox-active metal peripherals: enhancement of d[small pi]-p[small pi] interaction leading to unique assembly and redox-triggered remote switching of fluorescence. Dalton Trans 42(45):16108–16120
Cuesta L, Karnas E, Lynch VM, Sessler JL, Kajonkijya W, Zhu W, Zhang M, Ou Z, Kadish KM, Ohkubo K, Fukuzumi S (2008) (Pentamethylcyclopentadienyl)ruthenium π-complexes of metalloporphyrins: platforms with novel photo- and electrochemical properties. Chem Eur J 14(33):10206–10210
Yasu Y, Inagaki A, Akita M (2014) Synthesis of trinuclear Pd–Ru–Pd porphyrin complexes with axially ligated Pd centers. Prominent metal-to-ligand charge transfer band in the visible region. J Organomet Chem 753:48–54
Kojima T, Hanabusa K, Ohkubo K, Shiro M, Fukuzumi S (2010) Construction of SnIV porphyrin/trinuclear ruthenium cluster dyads linked by pyridine carboxylates: photoinduced electron transfer in the Marcus inverted region. Chem Eur J 16(12):3646–3655
Li P, Amirjalayer S, Hartl F, Lutz M, Bruin Bd, Becker R, Woutersen S, Reek JNH (2014) Direct probing of photoinduced electron transfer in a self-assembled biomimetic [2Fe2S]-hydrogenase complex using ultrafast vibrational spectroscopy. Inorg Chem 53(10):5373–5383
Song L-C, Tang M-Y, Mei S-Z, Huang J-H, Hu Q-M (2007) The active site model for iron-only hydrogenases coordinatively bonded to a metalloporphyrin photosensitizer. Organometallics 26(7):1575–1577
Li X, Wang M, Zhang S, Pan J, Na Y, Liu J, Åkermark B, Sun L (2008) Noncovalent assembly of a metalloporphyrin and an iron hydrogenase active-site model: photo-induced electron transfer and hydrogen generation. J Phys Chem B 112(27):8198–8202
Kluwer AM, Kapre R, Hartl F, Lutz M, Spek AL, Brouwer AM, van Leeuwen PWNM, Reek JNH (2009) Self-assembled biomimetic [2Fe2S]-hydrogenasebased photocatalyst for molecular hydrogen evolution. Proc Natl Acad Sci USA 106:10460–10465
Poddutoori P, Co DT, Samuel APS, Kim CH, Vagnini MT, Wasielewski MR (2011) Photoinitiated multistep charge separation in ferrocene-zinc porphyrin-diiron hydrogenase model complex triads. Energ Environ Sci 4(7):2441–2450
Gao W-Y, Chrzanowski M, Ma S (2014) Metal-metalloporphyrin frameworks: a resurging class of functional materials. Chem Soc Rev 43(16):5841–5866
Uvarova MA, Sinelshchikova AA, Golubnichaya MA, Nefedov SE, Enakieva YY, Gorbunova YG, Tsivadze AY, Stern C, Bessmertnykh-Lemeune A, Guilard R (2014) Supramolecular assembly of organophosphonate diesters using paddle-wheel complexes: first examples in porphyrin series. Cryst Growth Des 14(11):5976–5984
Milic TN, Chi N, Yablon DG, Flynn GW, Batteas JD, Drain CM (2002) Controlled hierarchical self-assembly and deposition of nanoscale photonic materials. Angew Chem Int Ed 41(12):2117–2119
Xiang Z, Xue Y, Cao D, Huang L, Chen J-F, Dai L (2014) Highly efficient electrocatalysts for oxygen reduction based on 2D covalent organic polymers complexed with non-precious metals. Angew Chem Int Ed 53(9):2433–2437
Wang Y, Deng K, Gui L, Tang Y, Zhou J, Cai L, Qiu J, Ren D, Wang Y (1999) Preparation and characterization of nanoscopic organic semiconductor of oxovanadium phthalocyanine. J Colloid Interface Sci 213(1):270–272
Alves E, Iglesias BA, Deda DK, Budu A, Matias TA, Bueno VB, Maluf FV, Guido RVC, Oliva G, Catalani LH, Araki K, Garcia CRS (2015) Encapsulation of metalloporphyrins improves their capacity to block the viability of the human malaria parasite Plasmodium falciparum. Nanomed Nanotechnol 11:351–358
Deda DK, Budu A, Cruz LN, Araki K, Garcia CRS (2015) Strategies for development of antimalarials based on encapsulated porphyrin derivatives. Mini-Rev Med Chem 141055–1071
Deda DK, Pavani C, Carita E, Baptista MS, Toma HE, Araki K (2012) Correlation of photodynamic activity and singlet oxygen quantum yields in two series of hydrophobic monocationic porphyrins. J Porphyrins Phthalocyanines 16(1):55–63
Deda DK, Pavani C, Carita E, Baptista MS, Toma HE, Araki K (2013) Control of cytolocalization and mechanism of cell death by encapsulation of a photosensitizer. J Biomed Nanotechnol 9(8):1307–1317
Deda DK, Uchoa AF, Carita E, Baptista MS, Toma HE, Araki K (2009) A new micro/nanoencapsulated porphyrin formulation for PDT treatment. Int J Pharm 376(1–2):76–83
Tomalia DA, Naylor AM, Goddard WA (1990) Starburst dendrimers: molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter. Angew Chem Int Ed 29(2):138–175
Newkome GR, Moorefield CN, Vögtle F (2008) Dendritic molecules: concepts, syntheses, perspectives. Wiley-VCH, Weinheim
Bosman AW, Janssen HM, Meijer EW (1999) About dendrimers: structure, physical properties, and applications. Chem Rev 99(7):1665–1688
Grayson SM, Fréchet JMJ (2001) Convergent dendrons and dendrimers: from synthesis to applications. Chem Rev 101(12):3819–3868
Gorman CB, Smith JC (2001) Structure-property relationships in dendritic encapsulation. Acc Chem Res 34(1):60–71
Majoral J-P, Caminade A-M (1999) Dendrimers containing heteroatoms (Si, P, B, Ge, or Bi). Chem Rev 99(3):845–880
Newkome GR, He E, Moorefield CN (1999) Suprasupermolecules with novel properties: metallodendrimers. Chem Rev 99(7):1689–1746
Deraedt C, Astruc D (2014) “Homeopathic” palladium nanoparticle catalysis of cross carbon-carbon coupling reactions. Acc Chem Res 47(2):494–503
He Y-M, Feng Y, Fan Q-H (2014) Asymmetric hydrogenation in the core of dendrimers. Acc Chem Res 47(10):2894–2906
Kannan RM, Nance E, Kannan S, Tomalia DA (2014) Emerging concepts in dendrimer-based nanomedicine: from design principles to clinical applications. J Int Med 276(6):579–617
Pikkemaat JA, Wegh RT, Lamerichs R, van de Molengraaf RA, Langereis S, Burdinski D, Raymond AYF, Janssen HM, de Waal BFM, Willard NP, Meijer EW, Grüll H (2007) Dendritic PARACEST contrast agents for magnetic resonance imaging. Contrast Media Mol I 2(5):229–239
Unciti-Broceta A, Díaz-Mochón JJ, Sánchez-Martín RM, Bradley M (2012) The use of solid supports to generate nucleic acid carriers. Acc Chem Res 45(7):1140–1152
Wolinsky JB, Grinstaff MW (2008) Therapeutic and diagnostic applications of dendrimers for cancer treatment. Adv Drug Deliv Rev 60(9):1037–1055
Zhang X, Zeng Y, Yu T, Chen J, Yang G, Li Y (2014) Advances in photofunctional dendrimers for solar energy conversion. J Phys Chem Lett 5(13):2340–2350
Flores-Rojas GG, Lijanova IV, Morales-Saavedra OG, Sanchez-Montes K, Martínez-García M (2013) Synthesis and NLO behavior of Oligo(phenylenevinylene)-Porphyrin Dendrimers. Dyes Pigm 96(1):125–129
Samoc M, Corkery TC, McDonagh AM, Cifuentes MP, Humphrey MG (2011) Organometallic complexes for non-linear optics. 49. Third-order non-linear optical spectral dependence studies of arylalkynylruthenium dendrimers. Aust J Chem 64(9):1269–1273
Tang M-C, Chan CK-M, Tsang DP-K, Wong Y-C, Chan MM-Y, Wong KM-C, Yam VW-W (2014) Saturated red-light-emitting gold(III) triphenylamine dendrimers for solution-processable organic light-emitting devices. Chem Eur J 20(46):15233–15241
Choi S, Drese JH, Jones CW (2009) Adsorbent materials for carbon dioxide capture from large anthropogenic point sources. ChemSusChem 2(9):796–854
Diallo MS, Christie S, Swaminathan P, Johnson JH, Goddard WA (2005) Dendrimer enhanced ultrafiltration. 1. Recovery of Cu(II) from aqueous solutions using PAMAM dendrimers with ethylene diamine core and terminal NH2 groups. Environ Sci Technol 39(5):1366–1377
Tailor R, Abboud M, Sayari A (2014) Supported polytertiary amines: highly efficient and selective SO2 adsorbents. Environ Sci Technol 48(3):2025–2034
Li W-S, Aida T (2009) Dendrimer porphyrins and phthalocyanines. Chem Rev 109(11):6047–6076
Jin R-H, Aida T, Inoue S (1993) ‘Caged’ porphyrin: the first dendritic molecule having a core photochemical functionality. J Chem Soc Chem Commun (16):1260–1262
Jiang D-L, Aida T (1996) A dendritic iron porphyrin as a novel haemoprotein mimic: effects of the dendrimer cage on dioxygen-binding activity. Chem Commun (13):1523–1524
Bhyrappa P, Young JK, Moore JS, Suslick KS (1996) Dendrimer-metalloporphyrins: synthesis and catalysis. J Am Chem Soc 118(24):5708–5711
Jiang D-L, Aida T (1998) Morphology-dependent photochemical events in aryl ether dendrimer porphyrins: cooperation of dendron subunits for singlet energy transduction. J Am Chem Soc 120(42):10895–10901
Zingg A, Felber B, Gramlich V, Fu L, Collman JP, Diederich F (2002) Dendritic iron(II) porphyrins as models for hemoglobin and myoglobin: specific stabilization of O2 complexes in dendrimers with H-bond-donor centers. Helv Chim Acta 85(1):333–351
Karasugi K, Kitagishi H, Kano K (2012) Modification of a dioxygen carrier, hemoCD, with PEGylated dendrons for extension of circulation time in the bloodstream. Bioconjug Chem 23(12):2365–2376
Blankenship RE, Madigan MT, Bauer CE (eds) (1995) Anoxygenic photosynthetic bacteria. Kluwer Academic, Netherlands
Choi M-S, Aida T, Yamazaki T, Yamazaki I (2001) A large dendritic multiporphyrin array as a mimic of the bacterial light-harvesting antenna complex: molecular design of an efficient energy funnel for visible photons. Angew Chem Int Ed 40(17):3194–3198
Paulo PMR, Costa SMB (2003) Non-covalent dendrimer-porphyrin interactions: the intermediacy of H-aggregates? Photochem Photobiol Sci 2(5):597–604
Paulo PMR, Costa SMB (2005) Interactions in noncovalent PAMAM/TMPyP systems studied by fluorescence spectroscopy. J Phys Chem B 109(29):13928–13940
Paulo PMR, Gronheid R, De Schryver FC, Costa SMB (2003) Porphyrin-dendrimer assemblies studied by electronic absorption spectra and time-resolved fluorescence. Macromolecules 36(24):9135–9144
Bo Z, Zhang L, Wang Z, Zhang X, Shen J (1999) Investigation of self-assembled dendrimer complexes. Mater Sci Eng, C 10(1–2):165–170
Brewis M, Clarkson GJ, Goddard V, Helliwell M, Holder AM, McKeown NB (1998) Silicon phthalocyanines with axial dendritic substituents. Angew Chem Int Ed 37(8):1092–1094
McKeown NB (1999) Phthalocyanine-containing dendrimers. Adv Mater 11(1):67–69
Sakamoto M, Ueno A, Mihara H (2000) Construction of [small alpha]-helical peptide dendrimers conjugated with multi-metalloporphyrins: photoinduced electron transfer on dendrimer architecture. Chem Commun (18):1741–1742
Sakamoto M, Ueno A, Mihara H (2001) Multipeptide-metalloporphyrin assembly on a dendrimer template and photoinduced electron transfer based on the dendrimer structure. Chem Eur J 7(11):2449–2458
Astruc D (2012) Electron-transfer processes in dendrimers and their implication in biology, catalysis, sensing and nanotechnology. Nat Chem 4(4):255–267
Ceroni P, Venturi M (2011) Photoactive and electroactive dendrimers: future trends and applications. Aust J Chem 64(2):131–146
Dandliker PJ, Diederich F, Gross M, Knobler CB, Louati A, Sanford EM (1994) Dendritic porphyrins: modulating redox potentials of electroactive chromophores with pendant multifunctionality. Angew Chem Int Ed 33(17):1739–1742
Dandliker PJ, Diederich F, Gisselbrecht J-P, Louati A, Gross M (1996) Water-soluble dendritic iron porphyrins: synthetic models of globular heme proteins. Angew Chem Int Ed 34(23–24):2725–2728
Kassner RJ (1973) Theoretical model for the effects of local nonpolar heme environments on the redox potentials in cytochromes. J Am Chem Soc 95(8):2674–2677
Weyermann P, Diederich F, Gisselbrecht J-P, Boudon C, Gross M (2002) Dendritic iron porphyrins with tethered axial ligands: new model compounds for cytochromes. Helv Chim Acta 85(2):571–598
Weyermann P, Gisselbrecht J-P, Boudon C, Diederich F, Gross M (1999) Dendritic iron porphyrins with tethered axial ligands: new model compounds for cytochromes. Angew Chem Int Ed 38(21):3215–3219
Cameron CS, Gorman CB (2002) Effects of site encapsulation on electrochemical behavior of redox-active core dendrimers. Adv Funct Mater 12(1):17–20
Gorman CB, Smith JC, Hager MW, Parkhurst BL, Sierzputowska-Gracz H, Haney CA (1999) Molecular structure-property relationships for electron-transfer rate attenuation in redox-active core dendrimers. J Am Chem Soc 121(43):9958–9966
Pollak KW, Leon JW, Fréchet JMJ, Maskus M, Abruña HD (1998) Effects of dendrimer generation on site isolation of core moieties: electrochemical and fluorescence quenching studies with metalloporphyrin core dendrimers. Chem Mater 10(1):30–38
Vögtle F, Plevoets M, Nieger M, Azzellini GC, Credi A, De Cola L, De Marchis V, Venturi M, Balzani V (1999) Dendrimers with a photoactive and redox-active [Ru(bpy)3]2+-type core: photophysical properties, electrochemical behavior, and excited-state electron-transfer reactions. J Am Chem Soc 121(26):6290–6298
Nierengarten J-F (2003) Dendritic encapsulation of active core molecules. CR Chim 6(8–10):725–733
Pani RC, Yingling YG (2012) Role of solvent and dendritic architecture on the redox core encapsulation. J Phys Chem A 116(28):7593–7599
Hogan CF, Harris AR, Bond AM, Sly J, Crossley MJ (2006) Electrochemical studies of porphyrin-appended dendrimers. Phys Chem Chem Phys 8(17):2058–2065
Archut A, Azzellini GC, Balzani V, De Cola L, Vögtle F (1998) Toward photoswitchable dendritic hosts. Interaction between azobenzene-functionalized dendrimers and eosin. J Am Chem Soc 120(47):12187–12191
Imaoka T, Tanaka R, Yamamoto K (2006) Synergetic activation of carbon dioxide molecule using phenylazomethine dendrimers as a catalyst. J Polym Sci A Polym Chem 44(17):5229–5236
Huang C-Y, Su YO (2010) Spectral and redox properties of zinc porphyrin core dendrimers with triarylamines as dendron. Dalton Trans 39(35):8306–8312
Loiseau F, Campagna S, Hameurlaine A, Dehaen W (2005) Dendrimers made of porphyrin cores and carbazole chromophores as peripheral units. Absorption spectra, luminescence properties, and oxidation behavior. J Am Chem Soc 127(32):11352–11363
Huang C-Y, Hsu C-Y, Yang L-Y, Lee C-J, Yang T-F, Hsu C-C, Ke C-H, Su YO (2012) A Systematic study of electrochemical and spectral properties for the electronic interactions in porphyrin-triphenylamine conjugates. Eur J Inorg Chem 7:1038–1047
Le Pleux L, Pellegrin Y, Blart E, Odobel F, Harriman A (2011) Long-lived, charge-shift states in heterometallic, porphyrin-based dendrimers formed via click chemistry. J Phys Chem A 115(20):5069–5080
Fukuzumi S, Saito K, Ohkubo K, Khoury T, Kashiwagi Y, Absalom MA, Gadde S, D’Souza F, Araki Y, Ito O, Crossley MJ (2011) Multiple photosynthetic reaction centres composed of supramolecular assemblies of zinc porphyrin dendrimers with a fullerene acceptor. Chem Commun 47(28):7980–7982
Costa SMB, Andrade SM, Togashi DM, Paulo PMR, Laia CAT, Isabel Viseu M, Gonçalves da Silva AM (2009) Optical spectroscopy and photochemistry of porphyrins and phthalocyanines. J Porphyrins Phthalocyanines 13:509–517
Paulo PMR, Lopes JNC, Costa SMB (2007) Molecular dynamics simulations of charged dendrimers: low-to-intermediate half-generation PAMAMs. J Phys Chem B 111(36):10651–10664
Paulo PMR, Lopes JNC, Costa SMB (2008) Molecular dynamics simulations of porphyrin-dendrimer systems: toward modeling electron transfer in solution. J Phys Chem B 112(47):14779–14792
Paulo PMR, Costa SMB (2012) Photoinduced electron-transfer in supramolecular complex of zinc porphyrin with poly(amido amine) dendrimer donor. J Photochem Photobiol A 234:66–74
Tada A, Geng Y, Wei Q, Hashimoto K, Tajima K (2011) Tailoring organic heterojunction interfaces in bilayer polymer photovoltaic devices. Nat Mater 10(6):450–455
Imaoka T, Ueda H, Yamamoto K (2012) Enhancing the photoelectric effect with a potential-programmed molecular rectifier. J Am Chem Soc 134(20):8412–8415
Giraudeau A, Ruhlmann L, El Kahef L, Gross M (1996) Electrosynthesis and characterization of symmetrical and unsymmetrical linear porphyrin dimers and their precursor monomers. J Am Chem Soc 118(12):2969–2979
Ruhlmann L, Schulz A, Giraudeau A, Messerschmidt C, Fuhrhop J-H (1999) A polycationic zinc-5,15-dichlorooctaethylporphyrinate-viologen wire. J Am Chem Soc 121(28):6664–6667
Hao J, Giraudeau A, Ping Z, Ruhlmann L (2008) Supramolecular assemblies obtained by large counteranion incorporation in a well-oriented polycationic copolymer. Langmuir 24(5):1600–1603
Schaming D, Ahmed I, Hao J, Alain-Rizzo V, Farha R, Goldmann M, Xu H, Giraudeau A, Audebert P, Ruhlmann L (2011) Easy methods for the electropolymerization of porphyrins based on the oxidation of the macrocycles. Electrochim Acta 56(28):10454–10463
Schaming D, Marggi-Poullain S, Ahmed I, Farha R, Goldmann M, Gisselbrecht J-P, Ruhlmann L (2011) Electrosynthesis and electrochemical properties of porphyrin dimers with pyridinium as bridging spacer. New J Chem 35(11):2534–2543
Ruhlmann L, Hao J, Ping Z, Giraudeau A (2008) Self-oriented polycationic copolymers obtained from bipyridinium meso-substituted-octaethylporphyrins. J Electroanal Chem 621(1):22–30
Xia Y, Schaming D, Farha R, Goldmann M, Ruhlmann L (2012) Bis-porphyrin copolymers covalently linked by pyridinium spacers obtained by electropolymerization from [small beta]-octaethylporphyrins and pyridyl-substituted porphyrins. New J Chem 36(3):588–596
Sadakane M, Steckhan E (1998) Electrochemical properties of polyoxometalates as electrocatalysts. Chem Rev 98(1):219–238
Yamase T (1998) Photo- and electrochromism of polyoxometalates and related materials. Chem Rev 98(1):307–326
Allain C, Favette S, Chamoreau L-M, Vaissermann J, Ruhlmann L, Hasenknopf B (2008) Hybrid organic–inorganic porphyrin–polyoxometalate complexes. Eur J Inorg Chem 22:3433–3441
Allain C, Schaming D, Karakostas N, Erard M, Gisselbrecht J-P, Sorgues S, Lampre I, Ruhlmann L, Hasenknopf B (2013) Synthesis, electrochemical and photophysical properties of covalently linked porphyrin-polyoxometalates. Dalton Trans 42(8):2745–2754
Azcarate I, Ahmed I, Farha R, Goldmann M, Wang X, Xu H, Hasenknopf B, Lacote E, Ruhlmann L (2013) Synthesis and characterization of conjugated Dawson-type polyoxometalate-porphyrin copolymers. Dalton Trans 42(35):12688–12698
Schaming D, Allain C, Farha R, Goldmann M, Lobstein S, Giraudeau A, Hasenknopf B, Ruhlmann L (2010) Synthesis and photocatalytic properties of mixed polyoxometalate-porphyrin copolymers obtained from anderson-type polyoxomolybdates. Langmuir 26(7):5101–5109
Schaming D, Costa-Coquelard C, Sorgues S, Ruhlmann L, Lampre I (2010) Photocatalytic reduction of Ag2SO4 by electrostatic complexes formed by tetracationic zinc porphyrins and tetracobalt Dawson-derived sandwich polyanion. Appl Catal A 373(1–2):160–167
Schaming D, Farha R, Xu H, Goldmann M, Ruhlmann L (2010) Formation and photocatalytic properties of nanocomposite films containing both tetracobalt Dawson-derived sandwich polyanions and tetracationic porphyrins. Langmuir 27(1):132–143
Ahmed I, Farha R, Goldmann M, Ruhlmann L (2013) A molecular photovoltaic system based on Dawson type polyoxometalate and porphyrin formed by layer-by-layer self assembly. Chem Commun 49(5):496–498
Muthukumar P, Abraham John S (2014) Gold nanoparticles decorated on cobalt porphyrin-modified glassy carbon electrode for the sensitive determination of nitrite ion. J Colloid Interface Sci 421:78–84
Li J, Tu W, Lei J, Tang S, Ju H (2011) Porphyrin-functionalized gold nanoparticles for selective electrochemical detection of peroxyacetic acid. Electrochim Acta 56(9):3159–3163
Shen Y, Zhan F, Lu J, Zhang B, Huang D, Xu X, Zhang Y, Wang M (2013) Preparation of hybrid films containing gold nanoparticles and cobalt porphyrin with flexible electrochemical properties. Thin Solid Films 545:327–331
Lu X, Zhi F, Shang H, Wang X, Xue Z (2010) Investigation of the electrochemical behavior of multilayers film assembled porphyrin/gold nanoparticles on gold electrode. Electrochim Acta 55(11):3634–3642
Tombe S, Antunes E, Nyokong T (2013) Electrospun fibers functionalized with phthalocyanine-gold nanoparticle conjugates for photocatalytic applications. J Mol Catal A 371:125–134
Tombe S, Chidawanyika W, Antunes E, Priniotakis G, Westbroek P, Nyokong T (2012) Physicochemical behavior of zinc tetrakis (benzylmercapto) phthalocyanine when used to functionalize gold nanoparticles and in electronspun fibers. J Photochem Photobiol A 240:50–58
Noda Y, Noro S-I, Akutagawa T, Nakamura T (2014) Gold nanoparticle assemblies stabilized by bis(phthalocyaninato)lanthanide(III) complexes through van der Waals interactions. Nature 4:3758
Brust M, Walker M, Bethell D, Schiffrin DJ, Whyman R (1994) Synthesis of thiolderivatized gold nanoparticles in a 2-phase liquid system. J Chem Soc Chem Commun 801–802
Ahmed MS, Jeong H, You J-M, Jeon S (2011) Electrocatalytic reduction of dioxygen at a modified glassy carbon electrode based on Nafion®-dispersed single-walled carbon nanotubes and cobalt–porphyrin with palladium nanoparticles in acidic media. Electrochim Acta 56(13):4924–4929
Chen S, Yuan R, Chai Y, Zhang L, Wang N, Li X (2007) Amperometric third-generation hydrogen peroxide biosensor based on the immobilization of hemoglobin on multiwall carbon nanotubes and gold colloidal nanoparticles. Biosens Bioelectron 22(7):1268–1274
Dong S, Li N, Zhang P, Li Y, Chen Z, Huang T (2012) Fabrication of hemoglobin/ionic liquid modified carbon paste electrode based on the electrodeposition of gold nanoparticles/CdS quantum dots and its electrochemical application. Electroanal 24(7):1554–1560
Qiu J-D, Peng H-P, Liang R-P, Xia X-H (2010) Facile preparation of magnetic core–shell Fe3O4@Au nanoparticle/myoglobin biofilm for direct electrochemistry. Biosens Bioelectron 25(6):1447–1453
Wang W, Zhang T-J, Zhang D-W, Li H-Y, Ma Y-R, Qi L-M, Zhou Y-L, Zhang X-X (2011) Amperometric hydrogen peroxide biosensor based on the immobilization of heme proteins on gold nanoparticles-bacteria cellulose nanofibers nanocomposite. Talanta 84(1):71–77
Wei N, Xin X, Du J, Li J (2011) A novel hydrogen peroxide biosensor based on the immobilization of hemoglobin on three-dimensionally ordered macroporous (3DOM) gold-nanoparticle-doped titanium dioxide (GTD) film. Biosens Bioelectron 26(8):3602–3607
Xuan J, Jia X-D, Jiang L-P, Abdel-Halim ES, Zhu J-J (2012) Gold nanoparticle-assembled capsules and their application as hydrogen peroxide biosensor based on hemoglobin. Bioelectrochemistry 84:32–37
Li Y, Yang W, Bai Y, Sun C (2006) Amperometric sensor for trichloroacetic acid based on myoglobin/colloidal gold nanoparticles immobilized in titania sol-gel matrix. Electroanal 18(5):499–506
Sun W, Qin P, Zhao R, Jiao K (2010) Direct electrochemistry and electrocatalysis of hemoglobin on gold nanoparticle decorated carbon ionic liquid electrode. Talanta 80(5):2177–2181
Jiang J, Fan W, Du X (2014) Nitrite electrochemical biosensing based on coupled graphene and gold nanoparticles. Biosens Bioelectron 51:343–348
Li J, Lei J, Wang Q, Wang P, Ju H (2012) Bionic catalysis of porphyrin for electrochemical detection of nucleic acids. Electrochim Acta 83:73–77
Condomitti U, Silveira AT, Condomitti GW, Toma SH, Araki K, Toma HE (2014) Silver recovery using electrochemically active magnetite coated carbon particles. Hydrometallurgy 147–148:241–245
Condomitti U, Zuin A, Novak MA, Araki K, Toma HE (2011) Magnetic coupled electrochemistry: exploring the use of superparamagnetic nanoparticles for capturing, transporting and concentrating trace amounts of analytes. Electrochem Commun 13(1):72–74
Condomitti U, Zuin A, Silveira AT, Araki K, Toma HE (2011) Direct use of superparamagnetic nanoparticles as electrode modifiers for the analysis of mercury ions from aqueous solution and crude petroleum samples. J Electroanal Chem 661(1):72–76
Condomitti U, Zuin A, Silveira AT, Araki K, Toma HE (2012) Magnetic nanohydrometallurgy: a promising nanotechnological approach for metal production and recovery using functionalized superparamagnetic nanoparticles. Hydrometallurgy 125–126:148–151
Condomitti U, Zuin A, Silveira AT, Toma SH, Araki K, Toma HE (2011) Superparamagnetic carbon electrodes: a versatile approach for performing magnetic coupled electrochemical analysis of mercury ions. Electroanal 23(11):2569–2573
Iijima S (1980) Direct observation of the tetrahedral bonding in graphitized carbon black by high resolution electron microscopy. J Cryst Growth 50(3):675–683
Deng K, Zhou J, Li X (2013) Noncovalent nanohybrid of cobalt tetraphenylporphyrin with graphene for simultaneous detection of ascorbic acid, dopamine, and uric acid. Electrochim Acta 114:341–346
Hijazi I, Bourgeteau T, Cornut R, Morozan A, Filoramo A, Leroy J, Derycke V, Jousselme B, Campidelli S (2014) Carbon nanotube-templated synthesis of covalent porphyrin network for oxygen reduction reaction. J Am Chem Soc 136(17):6348–6354
Tu W, Lei J, Jian G, Hu Z, Ju H (2010) Noncovalent assembly of picket-fence porphyrins on nitrogen-doped carbon nanotubes for highly efficient catalysis and biosensing. Chem Eur J 16(13):4120–4126
Wang C, Yuan R, Chai Y, Chen S, Zhang Y, Hu F, Zhang M (2012) Non-covalent iron(III)-porphyrin functionalized multi-walled carbon nanotubes for the simultaneous determination of ascorbic acid, dopamine, uric acid and nitrite. Electrochim Acta 62:109–115
Hu YQ, Xue ZH, He HX, Ai RX, Liu XH, Lu XQ (2013) Photoelectrochemical sensing for hydroquinone based on porphyrin-functionalized Au nanoparticles on graphene. Biosens Bioelectron 47:45–49
Wang R-X, Fan J-J, Fan Y-J, Zhong J-P, Wang L, Sun S-G, Shen X-C (2014) Platinum nanoparticles on porphyrin functionalized graphene nanosheets as a superior catalyst for methanol electrooxidation. Nanoscale 6:14999–15007
Jahan M, Bao QL, Loh KP (2012) Electrocatalytically active graphene-porphyrin MOF composite for oxygen reduction reaction. J Am Chem Soc 134(15):6707–6713
Tang HJ, Yin HJ, Wang JY, Yang NL, Wang D, Tang ZY (2013) Molecular architecture of cobalt porphyrin multilayers on reduced graphene oxide sheets for high-performance oxygen reduction reaction. Angew Chem Int Edit 52(21):5585–5589
Hijazi I, Jousselme B, Jegou P, Filoramo A, Campidelli S (2012) Formation of linear and hyperbranched porphyrin polymers on carbon nanotubes via a CuAAC “grafting from” approach. J Mater Chem 22(39):20936–20942
Le Ho KH, Rivier L, Jousselme B, Jegou P, Filoramo A, Campidelli S (2010) Zn-porphyrin/Zn-phthalocyanine dendron for SWNT functionalisation. Chem Commun 46(46):8731–8733
Palacin T, Khanh HL, Jousselme B, Jegou P, Filoramo A, Ehli C, Guldi DM, Campidelli S (2009) Efficient functionalization of carbon nanotubes with porphyrin dendrons via click chemistry. J Am Chem Soc 131(42):15394–15402
Han HS, Lee HK, You J-M, Jeong H, Jeon S (2014) Electrochemical biosensor for simultaneous determination of dopamine and serotonin based on electrochemically reduced GO-porphyrin. Sensors Actuat B 190:886–895
Walter RI (1952) Potentiometric studies of a sulfonated iron porphyrin. J Biol Chem 196(1):151–174
Davis DG, Bynum LM (1975) A study of the electrode kinetics of iron porphyrins. Bioelectrochem Bioenerg 2(3):184–190
Wilson GS, Neri BP (1973) Cyclic voltmmetry of porphyrins and metalloporphyrins. Ann NY Acad Sci 206(1):568–578
Lu X, Shan D, Yang J, Huang B, Zhou X (2013) Determination of m-dinitrobenzene based on novel type of sensor using thiol-porphyrin mixed monolayer-tethered polyaniline with intercalating fullerenols. Talanta 115:457–461
Lv M, Mei T, Zhang Ca, Wang X (2014) Selective and sensitive electrochemical detection of dopamine based on water-soluble porphyrin functionalized graphene nanocomposites. RSC Adv 4(18):9261–9270
Poursaberi T, Hassanisadi M (2012) Application of metalloporphyrin grafted-graphene oxide for the construction of a novel salicylate-selective electrode. J Porphyrins Phthalocyanines 16(10):1140–1147
Joseph R, Girish Kumar K (2010) Differential pulse voltammetric determination and catalytic oxidation of sulfamethoxazole using [5,10,15,20- tetrakis (3-methoxy-4-hydroxy phenyl) porphyrinato] Cu (II) modified carbon paste sensor. Drug Test Anal 2(6):278–283
Tu W, Lei J, Ju H (2009) Functionalization of carbon nanotubes with water-insoluble porphyrin in ionic liquid: direct electrochemistry and highly sensitive amperometric biosensing for trichloroacetic acid. Chem Eur J 15(3):779–784
van Staden JF, Stefan-van Staden RI (2010) Application of porphyrins in flow-injection analysis: a review. Talanta 80(5):1598–1605
Quintino MSM, Angnes L (2004) Batch injection analysis: an almost unexplored powerful tool. Electroanal 16(7):513–523
do Nascimento RF, Selva TMG, Ribeiro WF, Belian MF, Angnes L, Nascimento VB (2013) Flow-injection electrochemical determination of citric acid using a cobalt(II)–phthalocyanine modified carbon paste electrode. Talanta 105:354–359
Kawamura K, Ikoma K, Igarashi S, Hisamoto H, Yao T (2011) Flow injection analysis combined with a hydrothermal flow reactor: Application to kinetic determination of trace amounts of iridium using a water-soluble porphyrin. Talanta 84(5):1318–1322
Kawamura K, Nakai T, Ikoma K, Hisamoto H (2012) High-throughput Ru(III) analysis using the hydrothermal flow reactor-mediated FIA by the extreme acceleration of Ru(III) complexation with 1,10-phenanthroline. Talanta 99:415–419
Quintino MSM, Araki K, Toma HE, Angnes L (2008) New hydrazine sensors based on electropolymerized meso-tetra(4-sulphonatephenyl)porphyrinate manganese(III)/silver nanomaterial. Talanta 74(4):730–735
Araki K, Angnes L, Gutz I GR, Toma HE, Martins PR, Silva FL (2009) Flow injection analyzer for analysis of sulfide and nitrite for environmental monitoring, comprises reservoir for hydrogen, reservoir for standard solution, reservoir for reducing solution, and reservoir for carrier solution. BR Patent BR200905276-A2, Dec 2009
Beheshti SS, Sohbat F, Amini MK (2010) A manganese porphyrin-based sensor for flow-injection potentiometric determination of thiocyanate. J Porphyrins Phthalocyanines 14(02):158–165
Almeida SAA, Montenegro MCBSM, Sales MGF (2013) New and low cost plastic membrane electrode with low detection limits for sulfadimethoxine determination in aquaculture waters. J Electroanal Chem 709:39–45
Cuartero M, Amorim CG, Araújo AN, Ortuño JA, Montenegro MCBSM (2013) A SO2-selective electrode based on a Zn-porphyrin for wine analysis. Anal Chim Acta 787:57–63
Poursaberi T, Ganjali MR, Hassanisadi M (2012) A novel fluoride-selective electrode based on metalloporphyrin grafted-grapheneoxide. Talanta 101:128–134
Xiaodong S, Ying L, Fagen L, Yangqin L, Zhenghua S (2011) Subnanogram determination of aniracetam in pharmaceutical preparations and biofluids by flow injection analysis with chemiluminescence detection based on its enhancement of the myoglobin-luminol reaction. J AOAC Int 94(5):1461–1466
Fan D, Li G, Hao J (2010) Fabrication and electrocatalytic activities of porphyrin and 12-molybdophosphoric acid hybrid films. J Colloid Interface Sci 351(1):151–155
Ma J, Wu J, Zheng J, Liu L, Zhang D, Xu X, Yang X, Tong Z (2012) Synthesis, characterization and electrochemical behavior of cationic iron porphyrin intercalated into layered niobate. Microporous Mesoporous Mater 151:325–329
Wang D, Groves JT (2013) Efficient water oxidation catalyzed by homogeneous cationic cobalt porphyrins with critical roles for the buffer base. Proc Natl Acad Sci USA 110(39):15579–15584
Ramírez G, Ferraudi G, Chen YY, Trollund E, Villagra D (2009) Enhanced photoelectrochemical catalysis of CO2 reduction mediated by a supramolecular electrode of packed CoII(tetrabenzoporphyrin). Inorg Chim Acta 362(1):5–10
Yao SA, Ruther RE, Zhang L, Franking RA, Hamers RJ, Berry JF (2012) Covalent attachment of catalyst molecules to conductive diamond: CO2 reduction using “Smart” electrodes. J Am Chem Soc 134(38):15632–15635
Yan Y, Yao P, Mu Q, Wang L, Mu J, Li X, Kang S-Z (2011) Electrochemical behavior of amino-modified multi-walled carbon nanotubes coordinated with cobalt porphyrin for the oxidation of nitric oxide. Appl Surf Sci 258(1):58–63
Ajayi FF, Chae K-J, Kim K-Y, Choi M-j, Kim IS (2009) Photocurrent and photoelectrochemical hydrogen production with tin porphyrin and platinum nanowires immobilized with nafion on glassy carbon electrode. Int J Hydrogen Energ 34(1):110–114
Kruusenberg I, Mondal J, Matisen L, Sammelselg V, Tammeveski K (2013) Oxygen reduction on graphene-supported MN4 macrocycles in alkaline media. Electrochem Commun 33:18–22
Alenezi K, Ibrahim SK, Li P, Pickett CJ (2013) Solar fuels: photoelectrosynthesis of CO from CO2 at p-type Si using Fe porphyrin electrocatalysts. Chem Eur J 19(40):13522–13527
Wang W, Li X, Wang X, Shang H, Liu X, Lu X (2010) Comparative electrochemical behaviors of a series of SH-terminated-functionalized porphyrins assembled on a gold electrode by scanning electrochemical microscopy (SECM). J Phys Chem B 114(32):10436–10441
Lu X, Yuan H, Zuo G, Yang J (2008) Study of the size and separation of pinholes in the self-assembled thiol-porphyrin monolayers on gold electrodes. Thin Solid Films 516(18):6476–6482
Lu X, Li M, Yang C, Zhang L, Li Y, Jiang L, Li H, Jiang L, Liu C, Hu W (2006) Electron transport through a self-assembled monolayer of thiol-end-functionalized tetraphenylporphines and metal tetraphenylporphines. Langmuir 22(7):3035–3039
Vecchi A, Gatto E, Floris B, Conte V, Venanzi M, Nemykin VN, Galloni P (2012) Tetraferrocenylporphyrins as active components of self-assembled monolayers on gold surface. Chem Commun 48(42):5145–5147
Xue Z, Yang J, Zhi F, Wang W, Liu X, Lu X (2009) Preparation, characterization, and electrochemical behaviors of self-assembled monolayer on gold electrode surface with mercapto-derivatized cobaltous porphyrin. Anal Lett 42(4):668–677
Jana A, Ishida M, Kwak K, Sung YM, Kim DS, Lynch VM, Lee D, Kim D, Sessler JL (2013) Comparative electrochemical and photophysical studies of tetrathiafulvalene-annulated porphyrins and their ZnII complexes: the effect of metalation and structural variation. Chem Eur J 19(1):338–349
Nielsen KA, Levillain E, Lynch VM, Sessler JL, Jeppesen JO (2009) Tetrathiafulvalene porphyrins. Chem Eur J 15(2):506–516
Jia H, Schmid B, Liu S-X, Jaggi M, Monbaron P, Bhosale SV, Rivadehi S, Langford SJ, Sanguinet L, Levillain E, El-Khouly ME, Morita Y, Fukuzumi S, Decurtins S (2012) Tetrathiafulvalene-fused porphyrins via quinoxaline linkers: symmetric and asymmetric donor-acceptor systems. ChemPhysChem 13(14):3370–3382
Bill NL, Ishida M, Bähring S, Lim JM, Lee S, Davis CM, Lynch VM, Nielsen KA, Jeppesen JO, Ohkubo K, Fukuzumi S, Kim D, Sessler JL (2013) Porphyrins fused with strongly electron-donating 1,3-dithiol-2-ylidene moieties: redox control by metal cation complexation and anion binding. J Am Chem Soc 135(29):10852–10862
Osati S, Davarani SSH, Safari N, Banitaba MH (2011) Electrochemical synthesis of novel π-extended phenoxazine derivatives of porphyrincatecholes. Electrochim Acta 56(25):9426–9432
Sakurai T, Shi K, Sato H, Tashiro K, Osuka A, Saeki A, Seki S, Tagawa S, Sasaki S, Masunaga H, Osaka K, Takata M, Aida T (2008) Prominent electron transport property observed for triply fused metalloporphyrin dimer: directed columnar liquid crystalline assembly by amphiphilic molecular design. J Am Chem Soc 130(42):13812–13813
Karakostas N, Schaming D, Sorgues S, Lobstein S, Gisselbrecht JP, Giraudeau A, Lampre I, Ruhlmann L (2010) Photophysical, electro- and spectroelectro-chemical properties of the nonplanar porphyrin [ZnOEP(Py) 4+4 ,4Cl−] in aqueous media. J Photochem Photobiol A 213(1):52–60
Engelmann FM, Losco P, Winnischofer H, Araki K, Toma HE (2002) Synthesis, electrochemistry, spectroscopy and photophysical properties of a series of meso-phenylpyridylporphyrins with one to four pyridyl rings coordinated to [Ru(bipy)2Cl]+ groups. J Porphyrins Phthalocyanines 6(1):33–42
Kadish KM, E W, Zhan R, Khoury T, Govenlock LJ, Prashar JK, Sintic PJ, Ohkubo K, Fukuzumi S, Crossley MJ (2007) Porphyrin-diones and porphyrin-tetraones: reversible redox units being localized within the porphyrin macrocycle and their effect on tautomerism. J Am Chem Soc 129(20):6576–6588
Sun P, Zong H, Salaita K, Ketter JB, Barrett AGM, Hoffman BM, Mirkin CA (2006) Probing surface-porphyrazine reduction potentials by molecular design. J Phys Chem B 110(37):18151–18153
Gross AJ, Bucher C, Coche-Guerente L, Labbé P, Downard AJ, Moutet J-C (2011) Nickel (II) tetraphenylporphyrin modified surfaces via electrografting of an aryldiazonium salt. Electrochem Commun 13(11):1236–1239
Jiao J, Anariba F, Tiznado H, Schmidt I, Lindsey JS, Zaera F, Bocian DF (2006) Stepwise formation and characterization of covalently linked multiporphyrin-imide architectures on Si(100). J Am Chem Soc 128(21):6965–6974
Lee SU, Belosludov RV, Mizuseki H, Kawazoe Y (2008) The role of aromaticity and the π-conjugated framework in multiporphyrinic systems as single-molecule switches. Small 4(7):962–969
Lin T, Kuang G, Shang XS, Liu PN, Lin N (2014) Self-assembly of metal-organic coordination networks using on-surface synthesized ligands. Chem Commun 50(97):15327–15329
Garah ME, Ciesielski A, Marets N, Bulach V, Hosseini MW, Samori P (2014) Molecular tectonics based nanopatterning of interfaces with 2D metal-organic frameworks (MOFs). Chem Commun 50(82):12250–12253
So MC, Beyzavi MH, Sawhney R, Shekhah O, Eddaoudi M, Al-Juaid SS, Hupp JT, Farha OK (2015) Post-assembly transformations of porphyrin-containing metal-organic framework (MOF) films fabricated via automated layer-by-layer coordination. Chem Commun 51(1):85–88
Ikeda K, Sato S, Takahashi K, Masuda T, Murakoshi K, Uosaki K (2013) Surface optimization of optical antennas for plasmonic enhancement of photoelectrochemical reactions. Electrochim Acta 112:864–868
Deng S, Lei J, Huang Y, Cheng Y, Ju H (2013) Electrochemiluminescent quenching of quantum dots for ultrasensitive immunoassay through oxygen reduction catalyzed by nitrogen-doped graphene-supported hemin. Anal Chem 85(11):5390–5396
Wu J-W, Mei W-J, Yan Z-H, Liu J-C, Li H (2013) In situ spectroelectrochemical monitoring during the electrocatalytic oxidation of guanine on [Ru(bpy)2(MPyTMPP)Cl]+/ITO electrode. J Electroanal Chem 697:21–27
Lvova L, Galloni P, Floris B, Lundström I, Paolesse R, Natale C (2013) A ferrocene-porphyrin ligand for multi-transduction chemical sensor development. Sensors-Basel 13(5):5841–5856
Lv Y-Y, Xu W, Lin F-W, Wu J, Xu Z-K (2013) Electrospun nanofibers of porphyrinated polyimide for the ultra-sensitive detection of trace TNT. Sens Actuators B 184:205–211
Arıcan D, Erdoğmuş A, Koca A (2014) Electrochromism of the Langmuir-Blodgett films based on monophthalocyanines carrying redox active metal centers. Thin Solid Films 550:669–676
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Matias, T.A., Azzellini, G.C., Angnes, L., Araki, K. (2016). Supramolecular Hybrid Organic/Inorganic Nanomaterials Based on Metalloporphyrins and Phthalocyanines. In: Zagal, J., Bedioui, F. (eds) Electrochemistry of N4 Macrocyclic Metal Complexes. Springer, Cham. https://doi.org/10.1007/978-3-319-31332-0_1
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