Abstract
Porphyrins bearing nitro and amino substituents have been used as excellent synthons for further functionalization in order to obtain new compounds with adequate features for a wide range of applications. This chapter brings an update on the effort of several research groups to study the synthesis and reactivity features of meso-tetraarylporphyrins bearing those functionalities.
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References
Fisher H, Zeile K (1929) Synthese des hämatoporphyrins, protoporphyrins und hämins. Liebigs Ann Chem 468:98
Woodward RB, Ayer WA, Beaton JM, Bickelhaupt F, Bonnett R, Buchschacher P, Closs GL, Dutler H, Hannah J, Hauck FP, Itô S, Langemann A, Le Goff E, Leimgruber W, Lwowski W, Sauer J, Valenta Z, Voltz H (1960) The total synthesis of chlorophyll. J Am Chem Soc 82:3800
Pandey RK, Zheng G (2000) Porphyrins as photosensitizers in photodynamic therapy. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, San Diego
Aida T, Inoue S (2000) Metalloporphyrins as catalysts for precision macromolecular synthesis. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, San Diego
Chou J-H, Kosal ME, Nalwa HS, Rakow NA, Suslick KS (2000) Applications of porphyrins and metalloporphyrins to materials chemistry. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, San Diego
Ono N (2002) The nitro group in organic synthesis. Wiley-VCH, New York
Ricci A (2008) Amino group chemistry: from synthesis to the life sciences. Wiley-VCH, Weinheim
Meng GG, James BR, Skov KA (1994) Porphyrin chemistry pertaining to the design of anti-cancer drugs; part 1, the synthesis of porphyrins containing meso-pyridyl and meso-substituted phenyl functional groups. Can J Chem 72:1894
Thomas DW, Martell AE (1956) Tetraphenylporphine and some para-substituted derivatives. J Am Chem Soc 78:1335
Thomas DW, Martell AE (1956) Absorption spectra of para-substituted tetraphenylporphines. J Am Chem Soc 78:1338
Rothemund P (1935) Formation of porphyrins from pyrroles and aldehydes. J Am Chem Soc 57:2010
Lindsey JS (2000) Synthesis of meso-substituted porphyrins. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, Boston
Cavaleiro JAS, Tomé AC, Neves MGPMS (2010) meso-Tetraarylporphyrin derivatives: new synthetic methodologies. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science. World Scientific, Singapore
Bettelheim A, White BA, Raybuck SA, Murray RW (1987) Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins. Inorg Chem 26:1009
Chauhan SMS, Sahoo BB, Srinivas KA (2001) Microwave-assisted synthesis of 5,10,15, 20-tetraarylporphyrins. Synth Commun 31:33
Collman JP, Gagne RR, Christopher AR, Halbert TR, Lang G, Robinson WT (1975) “Picket fence porphyrins”. Synthetic models for oxygen binding hemoproteins. J Am Chem Soc 97:1427
Haesegawa E, Nemoto J, Kangyama T, Tsuchida E (1978) Oxygenation of polymer-covalently bonded metalloporphyrins. Macromolecules 11:947
Haesegawa E, Nemoto J-I, Kanayama T, Tsuchida E (1978) Syntheses and properties of vinyl monomers containing a meso-tetraphenylporphin ring and their copolymers. Eur Polym J 14:123
Tsuchida E (1979) Approaches to artificial macromolecular oxygen carriers. J Macromol Sci-Chem A13:545
Collman JP, Brauman JI, Doxsee KM, Halbert TR, Bunnenberg E, Linder RE, LaMar GN, Del Gaudio J, Lang G, Spartalian K (1980) Synthesis and characterization of “tailed picket fence” porphyrins. J Am Chem Soc 102:4182
Sun Y, Martell AE, Tsutsui M (1986) The synthesis and proton nuclear magnetic resonance study of some nitro- and amino-unsymmetrically meta-substituted tetraphenylporphyrins. J Heterocycl Chem 23:561
Little RG (1981) Notes on the synthesis of meso-substituted porphyrins from pyrryl carbinols and the mechanism of the Rothemund reaction. Heterocycl Chem 18:129
Schiavon MA, Iwamoto LS, Ferreira AG, Iamamoto Y, Zanoni MVB, Assis MD (2000) Synthesis and characterization of a novel series of meso(nitrophenyl) and meso(carboxyphenyl) substituted porphyrins. J Braz Chem Soc 11:458
Kruper WJ, Chamberlin TA (1988) US Patent 4,746,735
Kruper WJ, Chamberlin TA, Kochanny M (1989) Regiospecific aryl nitration of meso-substituted tetraarylporphyrins: a simple route to bifunctional porphyrins. J Org Chem 54:2753
Ostrowski S, Lopuszynska B (2003) Preparation of meso-tetraarylporphyrins nitrated in two neighboring aromatic rings. Synth Commun 33:4101
Ostrowski S, Mikus A, Lopuszynska B (2004) Synthesis of highly substituted meso-tetraarylporphyrins. Tetrahedron 60:11951
Luguya R, Jaquinod L, Fronczek FR, Vicente MGH, Smith KM (2004) Synthesis and reactions of meso-(p-nitrophenyl)porphyrins. Tetrahedron 60:2757
Smith NW, Dzyubam SV (2010) Efficient nitration of meso-tetraphenylporphyrin with nitronium tetrafluoroborate. Arkivoc vii:10
Jaquinod L (2000) Functionalization of 5,10,15,20-tetra-substituted porphyrins. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook. Academic, San Diego
Jonhson AW, Winter M (1975) Meso-addition reaction of meso-tetraphenylporphyrin. Chem Ind (London) 351
Cavaleiro JAS, Neves MGPMS, Hewlins MJE, Jackson AH (1986) Reactions of porphyrins with nitronium tetrafluoroborate in pyridine. J Chem Soc Perkin Trans 1:575
Catalano MM, Crossley MJ, Harding MM, King, LC (1984) Control of reactivity at the porphyrin periphery by metal ion co-ordination: a general method for specific nitration at the β-pyrrolic position of 5,10,15,20-tetraarylporphyrins. J Chem Soc Chem Commun 1535
Crossley MJ, Govenlock LJ, Prashar JK (1995) Synthesis of porphyrin-2,3,12,13- and −2,3,7,8-tetraones: building blocks for the synthesis of extended porphyrin arrays. J Chem Soc Chem Commun 2379
Dahal S, Krishnan V, Nethaji M (1998) Coordination aggregation of meso-aryl porphyrins. Proc Indian Acad Sci (Chem Sci) 110:37
Cavaleiro JAS, Hewlins MJE, Jackson AH, Neves MGPMS (1986) Structures of the ring-opened oxidation products from meso-tetraphenylporphyrin. J Chem Soc Chem Commun 142
Evans B, Smith KM, Cavaleiro JAS (1978) Bile pigment studies. Part 4. Some novel reactions of metalloporphyrins with thallium(III) and cerium(IV) salts. Ring cleavage of meso-tetraphenylporphyrin. J Chem Soc Perkin Trans 1 768
Giraudeau A, Callot HJ, Jordan J, Ezhar I, Gross M (1979) Substituent effects in the electroreduction of porphyrins and metalloporphyrins. J Am Chem Soc 101:3857
Hombrecher HK, Gherdan VM, Ohm S, Cavaleiro JAS, Neves MGPMS, Condesso MF (1993) Synthesis and electrochemical investigation of β-alkyloxy substituted meso-tetraphenylporphyrins. Tetrahedron 49:8569
Vicente MGH, Neves MGPMS, Cavaleiro JAS, Hombrecher HK, Koll D (1996) Electrochemical and spectroscopic properties of Cu(II) β-nitro-meso-tetra(pentafluorophenyl)porphyrins. Tetrahedron Lett 37:261
Sen A, Ray PC, Das PK, Krishnan V (1996) Metalloporphyrins for quadratic nonlinear optics. J Phys Chem 100:19611
Richeter S, Jeandon C, Gisselbrecht J-P, Graff R, Ruppert R, Callot H (2004) Synthesis of new porphyrins with peripheral conjugated chelates and their use for the preparation of porphyrin dimers linked by metal ions. Inorg Chem 43:251
Ostrowski S, Szerszen D, Ryszczuk M (2005) Electrophilic nitration of meso-tetraarylporphyrin complexes at the beta-pyrrolic position. Synthesis 819
Wyrebek P, Ostrowski S (2007) Synthesis of some β-nitro-meso-tetraphenylporphyrin derivatives. J Porphyr Phthalocyanines 11:822
Bartoli JF, Battioni P, De Poor WR, Mansuy D (1994) Synthesis and remarkable properties of iron β-polynitroporphyrins as catalysts for monooxygenation reactions. J Chem Soc Chem Commun 23
Ozette K, Battioni P, Leduc P, Bartoli J-F, Mansuy D (1998) A new manganese-β-heptanitro-porphyrin with extreme redox potentials: spectral electrochemical and catalytic properties. Inorg Chim Acta 272:4
Chauhan SMS, Kumar A, Srinivas KA (2004) β-Polynitration of 5,10,15,20-tetrakis (2,6-dichlorophenyl)porphyrins with HNO3 and Cu(NO3)2 on clay using microwave irradiation. Synth Commun 34:2673
Ostrowski S, Shim YK (2001) Selective derivatization of TPP on one phenyl ring by nitration and subsequent nucleophilic substitution of hydrogen. Bull Korean Chem Soc 11:1
Ostrowski S, Urbańska N, Mikus A (2003) Nucleophilic substitution of hydrogen in meso-nitroaryl-substituted porphyrins unprotected at the NH-centers in the core ring. Tetrahedron Lett 44:4373
Ostrowski S, Mikus A (2003) A new approach to the synthesis of porphyrin-fullerene dyads. Mol Divers 6:315
Ostrowski S, Grzyb S (2007) Transformation of nitro-5,10,15,20-tetraarylporphyrins into their amino/nitro-functionalized derivatives. Jordan J Chem 2:297
Ostrowski S, Grzyb S, Mikus A (2007) Direct amination of meso-tetraarylporphyrin derivatives – easy route to A3B-, A2BC-, and A2B2-type porphyrins bearing two nitrogen-containing substituents at the meso-positioned phenyl groups. Helvetica Chim Acta 90:2000
Zhi-jun S, Yang-yan O, Qin H, Dan-li Z, Zhang-ping C (2005) Novel substitution reactions of 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin with nucleophilic reagents. Wuhan Univ J Nat Sci 10:919
Baldwin JE, Crossley MJ, DeBernardis J (1982) Efficient peripheral functionalization of porphyrins. Tetrahedron 38:685
Catalano MM, Crossley MJ, Harding MM, King LC (1984) Control of reactivity at the porphyrin periphery by metal ion co-ordination: a general method for specific nitration at the β-pyrrolic position of 5,10,15,20-tetraarylporphyrins. J Chem Soc Chem Commun 1537
Crossley MJ, King LG, Pyke SM (1987) A new and highly efficient synthesis of hydroxyporphyrins. Tetrahedron 43:4569
Crossley MJ, King LG (1996) Reaction of metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with oxyanions. Temperature-dependent competition between nucleophilic addition and single-electron transfer processes. J Chem Soc Perkin Trans 1 1251
Crossley MJ, King LG (1993) A new method for regiospecific deuteration and reduction of 5,10,15,20-tetraphenylporphyrins: nucleophilic reaction of borohydride ion with 2-nitro-5,10,15,20-tetraphenylporphyrins. J Org Chem 58:4370
Crossley MJ, King LG, Newsom IA, Sheehan CS (1996) Investigation of a 'reverse' approach to extended porphyrin systems. Synthesis of a 2,3-diaminoporphyrin and its reactions with α-diones. J Chem Soc Perkin Trans 1 2675
Crossley MJ, Harding MM, Tansey CW (1994) A convenient synthesis of 2-alkyl-5,10,15, 20-tetraphenylporphyrins: reaction of metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with Grignard and organolithium reagents. J Org Chem 59:4433
Crossley MJ, Gosper JJ, King LG (1988) C-hydroxyarylation of tetraphenylporphyrin – convenient introduction of a functionality which is oriented towards the porphyrin centre. Tetrahedron Lett 29:1597
Crossley MJ, King LG, Simpson JL (1997) Solvent-dependent ambident nucleophilicity of phenoxide ion towards nitroporphyrins: synthesis of 2-hydroxyaryl- and 2-aryloxy-5,10,15,20-tetraphenylporphyrins by displacement of a nitro group. J Chem Soc Perkin Trans 1 3087
Guo Q-N, Li Z-Y, Chan W-H, Lau K-C, Crossley M (2010) Appending zinc tetraphenylporphyrin with an amine receptor at β-pyrrolic carbon for designing a selective histamine chemosensor. Supramol Chem 22:122
Chen Z, Hu Q, Zhai B, Jiang Z, Qin W (2007) Nucleophilic substitution on porphyrin ring: synthesis of 2-(2-hydroxynaphthyl)-5,10,15,20-tetraphenylporphyrin. Chin J Chem 55:251
Huang Q, Pan Z, Wang P, Chen Z, Zhang X, Xu H (2006) Zinc(II) and copper(II) complexes of β-substituted hydroxylporphyrins as tumor photosensitizers. Bioorg Med Chem Lett 16:3030
Pereira AMVM, Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Paz FAA, Cavaleiro JAS (2008) A new synthetic approach to N-arylquinolino[2,3,4-at]porphyrins from β-arylaminoporphyrins. J Org Chem 73:7353
Jaquinod L, Gros C, Olmstead MM, Antolovich M, Smith KM (1996) First syntheses of fused pyrroloporphyrins. Chem Commun 1475
Jaquinod L, Gros C, Khoury RG, Smith KM (1996) A convenient synthesis of functionalized tetraphenylchlorins. Chem Commun 2581
Shea KM, Jaquinod L, Smith KM (1998) Dihydroporphyrin synthesis: new methodology. J Org Chem 63:7013
Giuntini F, Faustino MAF, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2005) Synthesis and reactivity of 2-(porphyrin-2-yl)-1,3-dicarbonyl compounds. Tetrahedron 61:10454
Lacerda PSS, Silva AMG, Tomé AC, Neves MGPMS, Silva AMS, Cavaleiro JAS, Llamas-Saiz AL (2006) [1,2,3]Triazolo[4,5-b]porphyrins: new building blocks for porphyrinic materials. Angew Chem Int Ed 45:5487
Richeter S, Hadj-Aïssa A, Taffin C, van der Lee KA, Leclercq D (2007) Synthesis and structural characterisation of the first N-heterocyclic carbene ligand fused to a porphyrin. Chem Commun 2148
Richeter S, Jeandon C, Ruppert R, Callot HJ (2002) A modular approach to porphyrin oligomers using metal ions as connectors. Chem Commun 266
Lefebvre J-F, Leclercq D, Gisselbrecht J-P, Richeter S (2010) Synthesis, characterization, and electronic properties of metalloporphyrins annulated to exocyclic imidazole and imidazolium rings. Eur J Org Chem 1912
Tomé AC, Lacerda PSS, Neves MGPMS, Cavaleiro JAS (1997) meso-Arylporphyrins as dienophiles in Diels–Alder reactions: a novel approach to the synthesis of chlorins, bacteriochlorins and naphthoporphyrins. Chem Commun 1199
Silva AMG, Tomé AC, Neves MGPMS, Silva AMS, Cavaleiro JAS (1999) meso-Tetraarylporphyrins as dipolarophiles in 1,3-dipolar cycloaddition reactions. Chem Commun 1767
Tomé AC, Neves MGPMS, Cavaleiro JAS (2009) Porphyrins and other pyrrolic macrocycles in cycloaddition reactions. J Porphyr Phthalocyanines 13:408
Silva AMG, Tomé AC, Neves MGPMS, Cavaleiro JAS (2002) Porphyrins in 1,3-dipolar cycloaddition reactions: synthesis of a novel pyrazoline-fused chlorin and a pyrazole-fused porphyrin. Synlett 1155
Ostrowski S, Wyrębek P (2006) The first example of Diels–Alder cycloaddition of ortho-xylylenes to meso-tetraarylporphyrins containing electron-deficient β, β-double bonds. Tetrahedron Lett 47:8437
Rose E, Kossanyi A, Quelquejeu M, Soleilhavoup M, Duwavran F, Bernard N, Lecas A (1996) Synthesis of biomimetic heme precursors: the “double picket fence” 5,10,15, 20-tetrakis(2′,6′-dinitro-4′-tert-butylphenyl)porphyrin. J Am Chem Soc 118:1567
Weimin S, Qi S, Yucheng W, Lihong L, Jingchao T (2010) An alternative approach to amino porphyrins. J Heterocycl Chem 47:1221
Lipinska ME, Teixeira DMD, Laia CAT, Silva AMG, Rebelo SLH, Freire C (2013) β-Functionalized zinc(II)aminoporphyrins by direct catalytic hydrogenation. Tetrahedron Lett 54:110
George CD, Richardson T, Hofton ME, Vale CM, Neves MGPMS, Cavaleiro JAS (1999) Chlorine gas sensing using thin films of meso-tetra(p-stearamidophenyl)porphyrin. Mater Sci Eng C 8–9:559
Kadish KM, Araullo-McAdams C, Han BC, Franzen MM (1990) Syntheses and spectroscopic characterization of (T(p-Me2N)F4PP)H2 and (T(p-Me2N)F4PP)M where T(p-Me2N)F4PP = the dianion of meso-tetrakis(o, o, m, m-tetrafluoro-p-(dimethylamino)phenyl) porphyrin and M = cobalt(II), copper(II), or nickel(II). Structures of (T(p-Me2N)F4PP)Co and meso-tetrakis(pentafluorophenyl)porphinatocobalt(II), (TF5PP)Co. J Am Chem Soc 112:8364
Costa JIT, Tomé AC, Neves MGPMS, Cavaleiro JAS (2011) 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin: a versatile platform to novel porphyrinic materials. J Porphyr Phthalocyanines 15:1117
Collman JP, Gagne RR, Halbert TR, Marchon JC, Reed CA (1973) Reversible oxygen adduct formation in ferrous complexes derived from a picket fence porphyrin. Model for oxymyoglobin. J Am Chem Soc 95:7868
Baldwin JE, Perlmutter P (1984) Bridged, capped and fenced porphyrins. In: Vögtle F, Weber E (eds) Topics in current chemistry. Springer, Berlin
Tomé AC, Silva AMS, Alkorta I, Elguero J (2011) Atropoisomerism and conformational aspects of meso-tetraarylporphyrins and related compounds. J Porphyr Phthalocyanines 15:1
Sessler JL, Karnas E, Sedenberg E (2012) Porphyrins and expanded porphyrins as receptors. In: Philip A, Jonathan W (eds) Supramolecular chemistry: from molecules to nanomaterials. Wiley, Chichester
Collman JP, Boitrel B, Fu L, Galanter J, Straumanis A, Rapta M (1997) The chloroacetamido group as a new linker for the synthesis of hemoprotein analogues. J Org Chem 62:2308
Collman JP, Wang Z, Straumanis A (1998) Isocyanate as a versatile synthon for modular synthesis of functionalized porphyrins. J Org Chem 63:2424
Lindsey JS (1980) Increased yield of a desired isomer by equilibriums displacement on binding to silica gel, applied to meso-tetrakis(o-aminophenyl)porphyrin. J Org Chem 45:5215
Lee C, Lee DH, Hong J-I (2001) Colorimetric anion sensing by porphyrin-based anion receptors. Tetrahedron Lett 42:8665
Ladomenou K, Bonar-Law RP (2002) Urea porphyrins as simple receptors for sugars. Chem Commun 2108
Cormode DP, Murray SS, Cowley AR, Beer PD (2006) Sulfate selective anion recognition by a novel tetra-imidazolium zinc metalloporphyrin receptor. Dalton Trans 5135
Cormode DP, Drew MGB, Jagessar R, Beer PD (2008) Metalloporphyrin anion sensors: the effect of the metal centre on the anion binding properties of amide-functionalised and tetraphenyl metalloporphyrins. Dalton Trans 6732
Beer PD, Cormode DP, Davis JJ (2004) Zinc metalloporphyrin-functionalised nanoparticle anion sensors. Chem Commun 414
David P, Cormode DP, Drew MGB, Jagessar R, Beer PD (2008) Anion sensing porphyrin functionalized nanoparticles. J Inorg Organomet Polym 18:32
Dixon IM, Lopez F, Tejera AM, Esteve J, Blasco MA, Pratviel G, Meunier B (2007) A G-quadruplex ligand with 10000-fold selectivity over duplex DNA. J Am Chem Soc 129:1502
Brown A, Beer PD (2012) Porphyrin-functionalised rotaxanes for anion recognition. Dalton Trans 41:118
Giuntini F, Alonso CMA, Boyle RW (2011) Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins. Photochem Photobiol Sci 10:759
Chen B, Li A, Liang F, Zhou X, Cao X, He Z (2006) Synthesis of some multi-β-substituted cationic porphyrins and studies on their interaction with DNA. Tetrahedron 62:5487
Silva EMP, Serra VV, Ribeiro AO, Tomé JPC, Domingues P, Faustino MAF, Neves MGPMS, Tomé AC, Cavaleiro JAS, Ferrer-Correia AJ, Iamamoto Y, Domingues MRM (2006) Characterization of cationic glycoporphyrins by electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 20:3605
Khan MM, Ali H, van Lier JE (2001) Synthesis of new aminoporphyrins via palladium-catalysed cross-coupling reactions. Tetrahedron Lett 42:1615
Soares ARM, Martínez-Díaz MV, Bruckner A, Pereira AMVM, Tomé JPC, Alonso CMA, Faustino MAF, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS, Torres T, Guldi DM (2007) Synthesis of novel N-linked porphyrin-phthalocyanine dyads. Org Lett 9:1557
Pereira AMVM, Neves MGPMS, Cavaleiro JAS, Jeandon C, Gisselbrecht J-P, Choua S, Ruppert R (2011) Diporphyrinylamines: synthesis and electrochemistry. Org Lett 13:4742
Pereira AMVM, Neves MGPMS, Cavaleiro JAS, Gisselbrecht J-P, Jeandon C, Ruppert R (2011) A new approach to N-phenylquinolino[2,3,4-at]porphyrins. Electrochemical and photochemical studies. J Porphyr Phthalocyanines 15:575
Fuhrhop J-H (1978) Irreversible reactions on the porphyrin periphery (excluding oxidations, reductions, and photochemical reactions). In: Dolphin D (ed) The porphyrins, vol 2. Academic, New York
Guo Z, Du F, Ren D, Chen Y, Zheng J, Liuc Z, Tian J (2006) Covalently porphyrin-functionalized single-walled carbon nanotubes: a novel photoactive and optical limiting donor–acceptor nanohybrid. J Mater Chem 16:3021
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 13:1236
Hombrecher HK, Gerdan VM, Cavaleiro JAS, Neves MGPMS (1994) An efficient synthesis of β-alkyloxy substituted porphyrins. J Prak Chem-Chem Ztg 336:542
Cavaleiro JAS, Gerdan VM, Hombrecher HK, Neves MGPMS, Silva A (1997) Synthesis and characterization of new 2-diazo-3-oxo-5,10,15,20-tetraphenylchlorins. Heterocycl Commun 3:253
Shen D-M, Liu C, Chen Q-Y (2007) Synthesis and versatile reactions of β-azidotetraarylporphyrins. Eur J Org Chem 1419
Shen D-M, Liu C, Shen Q-Y (2007) Synthesis and versatile reactions of β-azidotetraarylporphyrins. Eur J Org Chem 2888
Séverac M, Pleux LL, Scarpaci A, Blart E, Odobel F (2007) Synthesis of new azido porphyrins and their reactivity in copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction with alkynes. Tetrahedron Lett 48:6518
Ludke K, Alonso CMA, Neves MGPMS, Silva AMS, Cavaleiro JAS, Hombrechner HK (1997) A new approach to the synthesis of unsaturated porphyrins. Heterocycl Commun 3:503
Alonso CMA, Neves MGPMS, Silva AMS, Cavaleiro JAS, Hombrecher HK (1997) Reaction of β-amino-meso-tetraphenylporphyrin with α, β-unsaturated carbonyl compounds: an approach to fused pyridinoporphyrins. Tetrahedron Lett 38:2757
Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2000) Synthesis and Diels-Alder reactions of 2-(buta-1,3-dien-2-yl)-5,10,15,20-tetraphenylporphyrin. Tetrahedron Lett 41:5679
Tomé JPC, Pereira AMVM, Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS, Martinez-Diaz MV, Torres T, Rahman GMA, Rarney J, Guldi DM (2006) Synthesis and photophysical studies of new porphyrin–phthalocyanine dyads with hindered rotation. Eur J Org Chem 257
Kawakami T, Igarashi S (1996) Highly sensitive spectrophotometric determination of nitrite ion using 5,10,15,20-tetrakis(4-aminophenyl)porphine for application to natural waters. Anal Chim Acta 333:175
Kawakami T, Igarashi S (1997) Asymmetric porphyrin derivative having one reactive site as a highly sensitive spectrophotometric reagent for nitrite. Anal Chim Acta 354:159
Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2006) Reaction of 2-amino-5,10,15,20-tetraphenylporphyrinatonickel(ii) with α, β-unsaturated acyl chlorides: synthesis of 2-pyridone-fused porphyrin derivatives. J Mex Chem Soc 50:100
Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2001) Hetero-Diels–Alder reactions of β-imino-meso-tetraphenylporphyrin derivatives: a new approach to pyrido[2,3-b]porphyrins. Tetrahedron Lett 42:8307
Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2004) β-Imino-meso-tetraphenylporphyrin derivatives in hetero-Diels-Alder reactions. Eur J Org Chem 3233
Alonso CMA, Serra VV, Neves MGPMS, Tomé AC, Silva AMS, Paz FAA, Cavaleiro JAS (2007) An easy synthetic approach to pyridoporphyrins by domino reactions. Org Lett 9:2305
Gomes ATPC, Paz FAA, Neves MGPMS, Tomé AC, Silva AMS, Souza MCBV, Ferreira VF, Cavaleiro JAS (2011) Synthesis and characterization of new porphyrin/4-quinolone conjugates. Tetrahedron Lett 37:4741
Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS (2006) Beta-imino-meso-tetraphenylporphyrin derivatives: reactivity towards ethyl diazoacetate. Jordan J Chem 1:95
Crossley MJ, King LJ (1984) Novel heterocyclic systems from selective oxidation at the β-pyrrolic position of porphyrins. J Chem Soc Chem Commun 920
Beavington R, Rees PA, Burn PL (1998) A study on the oxidation of 2-hydroxyporphyrins to porphyrin-α-diones. J Chem Soc Perkin Trans 1 2847
Promarak V, Burn PL (2001) A new synthetic approach to porphyrin-α-diones and a-2,3,12,13-tetraone: building blocks for laterally conjugated porphyrin arrays. J Chem Soc Perkin Trans 1 14
Khoury T, Crossley MJ (2009) Expansion of the porphyrin π-system: stepwise annelation of porphyrin β, β′-pyrrolic faces leading to trisquinoxalinoporphyrin. New J Chem 33:1076
Gautam P, Krishnan V (1995) Coordination aggregation of meso-aryl substituted porphyrins. Proc Indian Acad Sci 107:477
Richeter S, Jeandon C, Ruppert R, Callot HJ (2001) Porphyrins acting as external and internal ligands: preparation of conjugated trimetallic dimeric porphyrins. Chem Commun 91
Richeter S, Jeandon C, Gisselbrecht JP, Ruppert R, Callot HJ (2002) Syntheses and optical and electrochemical properties of porphyrin dimers linked by metal ions. J Am Chem Soc 124:6168
Henrick K, Owston PG, Peters R, Tasker PA, Dell A (1980) Cyclisation involving a meso-phenyl substituent of a metalloporphyrin: X-ray structure of 5,10,15-triphenyl{22-oxo-benzo[2324]cyclohexa[a, b]porphinato(2-)}copper(II). Inorg Chim Acta 45:161
Callot HJ, Schaeffer E, Cromer R, Metz F (1990) Unexpected routes to naphtoporphyrin derivatives. Tetrahedron 46:5253
Ishkov YV, Zhilina ZI (1995) Porphyrins and their derivatives. 17. Intramolecular cyclization of 2-formyl-5,10,15,20-tetraphenylporphyrin complexes. Zh Org Khim 31:136
Richeter S, Jeandon C, Sauber C, Gisselbrecht JP, Ruppert R, Callot HJ (2002) Preparation, mass spectrometry and electrochemical studies of metal connected porphyrin oligomers. J Porphyr Phthalocyanines 6:423
Richeter S, Jeandon C, Gisselbrecht JP, Ruppert R, Callot HJ (2007) Synthesis, structural characterization, and electrochemical studies of nickel porphyrins bearing two peripheral conjugated chelating groups. Inorg Chem 46:10241
Ishkov YV (2001) Porphyrins and their derivatives: XXII. A new product of intramolecular cyclization of 5,10,15,20-tetraphenyl-2-formylporphyrin copper complex. Russ J Org Chem 37:288
Acknowledgments
Authors are grateful to “Fundação para a Ciência e a Tecnologia – FCT”, Lisbon, for funding QOPNA (the Research Unit in Organic Chemistry and projects). Thanks are also due to FCT for grants awarded to PhD and Post-Doc students. Thanks are also due to the University of Aveiro and to students involved in the work carried out in Aveiro.
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Serra, V.I.V., Pires, S.M.G., Alonso, C.M.A., Neves, M.G.P.M.S., Tomé, A.C., Cavaleiro, J.A.S. (2013). Meso-Tetraarylporphyrins Bearing Nitro or Amino Groups: Synthetic Strategies and Reactivity Profiles. In: Paolesse, R. (eds) Synthesis and Modifications of Porphyrinoids. Topics in Heterocyclic Chemistry, vol 33. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2013_101
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DOI: https://doi.org/10.1007/7081_2013_101
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