Advertisement

How to Design Donor–Acceptor Based Heterocyclic Conjugated Polymers for Applications from Organic Electronics to Sensors

  • K. Mahesh
  • Subramanian KarpagamEmail author
  • K. Pandian
Review
  • 125 Downloads

Abstract

Over the past few years, significant progress has been made in the design of organic semi-conducting conjugated polymers that readily transport holes or electrons and can result in light emission. The conjugated backbone consist mainly of electron-donating (donor) and electron-withdrawing (acceptor) units as alternating groups in a conjugated oligomer or polymer that can be regulated by physical properties such as π conjugation length, monomer alteration, inter/intramolecular interactions and energy levels. Certainly, it is notable today that the highest occupied molecular orbital level of the producing material is localized predominantly on the electron-donating moiety and lowest unoccupied molecular orbital level on the electron-accepting moiety. Conjugated oligomers or polymers are used in many detecting fields due to their exceptional ability to sense toxic chemicals, metal ions and biomolecules. The conjugated polymers have unique delocalized π-electronic “molecular wires” that can expand the fluorescence intensity considerably. The fluorescence intensity of polymers can be quenched by particular quenching molecules. In this review, the fluorescence intensity, detecting of multiple metal ions, solubility, photochemical stability and optoelectronic properties of these conjugated polymers, and how they can be regulated by different functional groups, are discussed in detail.

Keywords

Conjugated polymer Inter/intramolecular interactions Toxic chemicals Fluorescence intensity Optoelectronic properties 

Notes

Acknowledgement

The authors would like to acknowledge the VIT University for supporting this work.

References

  1. 1.
    Kushida S, Braam D, Dao TD, Saito H, Shibasaki K, Ishii S, Nagao Y, Cui A, Kuwabara J, Kanbara T, Kijima M, Lorke A, Yamamoto Y (2016) Conjugated polymer blend microsphere for efficient, long range light energy transfer. ACS Nano 10:5543–5549PubMedGoogle Scholar
  2. 2.
    Naarmann H (2000) Polymers electrically conducting, ullmann’s encyclopedia of industrial chemistryGoogle Scholar
  3. 3.
    Akamatu H, Inokuchi H, Matsunaga Y (1954) Electrical conductivity of the perylene–bromine complex. Nature 173(4395):168–169Google Scholar
  4. 4.
    Ferraris J, Cowan DO, Walatka VT, Perlstein JH (1973) Electron transfer in a new highly conducting donor-acceptor complex. J Am Chem Soc 95(3):948–949Google Scholar
  5. 5.
    Bolto BA, McNeill R, Weiss DE (1963) Electronic conduction in polymers. III. Electronic properties of polypyrrole. Aust J Chem 16(6):1090–1103Google Scholar
  6. 6.
    De Surville R, Jozefowicz M, Yu LT, Pepichon J, Buvet R (1968) Electrochemical chains using protolytic organic semiconductors. Electrochim Acta 13(6):1451–1458Google Scholar
  7. 7.
    Shirakawa H, Louis EJ, MacDiarmid AG, Chiang CK, Heeger AJ (1977) Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH)x. J Chem Soc Chem Commun 37:578–580Google Scholar
  8. 8.
    Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Holmes AB (1990) Light-emitting diodes based on conjugated polymers. Nature 347(6293):539–541Google Scholar
  9. 9.
    Friend RH, Gymer RW, Holmes AB, Burroughes JH (1999) Electroluminescence in conjugated polymers. Nature 397(6715):121Google Scholar
  10. 10.
    Holdcroft S (2001) Patterning pi-conjugated polymers. Adv Mater 13(23):1753–1765Google Scholar
  11. 11.
    Gierschner J, Cornil J, Egelhaaf HJ (2007) Optical bandgaps of π-conjugated organic materials at the polymer limit: experiment and theory. Adv Mater 19(2):173–191Google Scholar
  12. 12.
    Leger JM (2008) Organic electronics: the ions have it. Adv Mater 20(4):837–841Google Scholar
  13. 13.
    Hameed S, Predeep P, Baiju MR (2010) Polymer light emitting diodes-a review on materials and techniques. Rev Adv Mater Sci 26:30–42Google Scholar
  14. 14.
    Sonar P, Williams EL, Singh SP, Dodabalapur A (2011) Thiophene–benzothiadiazole–thiophene (D–A–D) based polymers: effect of donor/acceptor moieties adjacent to D-A–D segment on photophysical and photovoltaic properties. J Mater Chem 21(28):10532–10541Google Scholar
  15. 15.
    Akpinar HZ, Udum YA, Toppare L (2015) Multichromic and soluble conjugated polymers containing thiazolothiazole unit for electrochromic applications. Eur Polym J 63:255–261Google Scholar
  16. 16.
    Fukuda K, Maki I, Ikeda S, Ito S (1993) Microtextures formed by the remelting reaction in belite crystals. J Am Ceram Soc 76:2942–2944Google Scholar
  17. 17.
    Wnek EG, Chien JCW, Karasz FE, Lillya CP (1979) Electrically conducting derivatives of poly(p-phenylene vinylene). Polymer 20:1441–1443Google Scholar
  18. 18.
    Kanazawa KK, Diaz AF, Geiss RH, Gill WD, Kwak JF, Logan JA, Rabolt JF, Street B (1979) Organic metals’polypyrrole a stable synthetic metallic polymer. Chem Commun 12:854–855Google Scholar
  19. 19.
    Diaz AF, Logan JA (1980) Electroactive polyaniline films. J Electroanal Chem Interfacial Electrochem 111(1):111–114Google Scholar
  20. 20.
    Waltman RJ, Bargon J, Diaz AF (1983) Electrochemical studies of some conducting polythiophene films. J Phys Chem 87:1459–1463Google Scholar
  21. 21.
    Heeger AJ (2001) Nobel lecture: semiconducting and metallic polymers: The fourth generation of polymeric materials. Rev Mod Phys 73(3):681–700Google Scholar
  22. 22.
    Yamamoto T, Senechika K, Yamamoto A (1980) Preparation of thermostable and electric-conducting poly (2,5-thienylene). J Polym Sci 18:9–12Google Scholar
  23. 23.
    Champion RD, Cheng KF, Pai CL, Chen WC, Jenekhe SA (2005) Electronic properties and field-effect transistors of thiophene-based donor–acceptor conjugated copolymers. Macromol Rapid Commun 26(23):1835–1840Google Scholar
  24. 24.
    Chen B, Wu Y, Wang M, Wang S, Sheng S, Zhu W, Tian H (2004) Novel fluorene-alt-thienylenevinylene-based copolymers: tuning luminescent wavelength via thiophene substitution position. Eur Polymer J 40(6):1183–1191Google Scholar
  25. 25.
    Do TT, Ha YE, Kim JH (2013) Effect of the number of thiophene rings in polymers with 2,1,3-benzooxadiazole core on the photovoltaic properties. Org Electron 14(10):2673–2681Google Scholar
  26. 26.
    Muhalbacher D, Scharber M, Morana M, Zhu Z, Waller D, Gaudiana R, Brabec C (2006) High photovoltaic performance of a low-bandgap polymer. Adv Mater 18(21):2884–2889Google Scholar
  27. 27.
    Sonar P, Singh SP, Leclere P, Surin M, Lazzaroni R, Lin TT, Sellinger A (2009) Synthesis, characterization and comparative study of thiophene–benzothiadiazole based donor–acceptor–donor (D–A–D) materials. J Mater Chem 19(20):3228–3237Google Scholar
  28. 28.
    Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Holmes AB (1990) Light-emitting diodes based on conjugated polymers. Nature 347(6293):539–541Google Scholar
  29. 29.
    Masse MA, Martin DC, Thomas E, Karasz FE, Petermann JH (1990) Crystal morphology in pristine and doped films of poly(p-phenylene vinylene). J Mater Sci 25(1):311–320Google Scholar
  30. 30.
    Alam MM, Jenekhe SA (2002) Polybenzobisazoles are efficient electron transport materials for improving the performance and stability of polymer light-emitting diodes. Chem Mater 14(11):4775–4780Google Scholar
  31. 31.
    Hou J, Yang C, Qiao J, Li Y (2005) Synthesis and photovoltaic properties of the copolymers of 2-methoxy-5-(2′-ethylhexyloxy)-1, 4-phenylene vinylene and 2, 5-thienylene-vinylene. Synth Met 150(3):297–304Google Scholar
  32. 32.
    Sanchez CO, Sobarzo P, Gatica N (2015) Electronic and structural properties of polymers based on phenylene vinylene and thiophene units. Control of the gap by gradual increases of thiophene moieties. New J Chem 39(10):7979–7987Google Scholar
  33. 33.
    Wong WY, Wang XZ, He Z, Chan KK, Djurišić AB, Cheung KY, Chan WK (2007) Tuning the absorption, charge transport properties, and solar cell efficiency with the number of thienyl rings in platinum-containing poly (aryleneethynylene) s. J Am Chem Soc 129(46):14372–14380PubMedGoogle Scholar
  34. 34.
    Zhang M, Fan H, Guo X, He Y, Zhang Z, Min J, Zhang J, Zhao G, Zhan X, Li Y (2010) Synthesis and photovoltaic properties of bithiazole-based donor-acceptor copolymers. Macromolecules 43(13):5706–5712Google Scholar
  35. 35.
    Zhou E, Cong J, Wei Q, Tajima K, Yang C, Hashimoto K (2011) All-polymer solar cells from perylene diimide based copolymers: material design and phase separation control. Angew Chem Int Ed 50(12):2799–2803Google Scholar
  36. 36.
    Havinga EE, Ten Hoeve W, Wynberg H (1993) Alternate donor–acceptor small-band-gap semiconducting polymers; Polysquaraines and polycroconaines. Synth Metals 55(1):299–306Google Scholar
  37. 37.
    Kitamura C, Tanaka S, Yamashita Y (1996) Design of narrow-bandgap polymers: syntheses and properties of monomers and polymers containing aromatic-donor and o-quinoid-acceptor units. Chem Mater 8(2):570–578Google Scholar
  38. 38.
    Jayakannan M, Van Hal PA, Janssen RA (2002) Synthesis and structure-property relationship of new donor–acceptor-type conjugated monomers and polymers on the basis of thiophene and benzothiadiazole. J Polym Sci Part A Polym Chem 40(2):251–261Google Scholar
  39. 39.
    Sivula K, Luscombe CK, Thompson BC, Fréchet JM (2006) Enhancing the thermal stability of polythiophene: fullerene solar cells by decreasing effective polymer regioregularity. J Am Chem Soc 128(43):13988–13989PubMedGoogle Scholar
  40. 40.
    Zhou H, Yang L, You W (2012) Rational design of high performance conjugated polymers for organic solar cells. Macromolecules 45(2):607–632Google Scholar
  41. 41.
    Son HJ, He F, Carsten B, Yu L (2011) Are we there yet? Design of better conjugated polymers for polymer solar cells. J Mater Chem 21:18934–18945Google Scholar
  42. 42.
    Keshtov ML, Sharma GD, Kochurov VS, Khokhlov AR (2013) New donor–acceptor conjugated polymers based on benzo[1,2-b:4,5-b]dithiophene for photovoltaic cells. Synth Met 166:7–13Google Scholar
  43. 43.
    Karpagam S, Guhanathan S (2014) Emitting oligomer containing quinoline group: synthesis and photophysical properties of conjugated oligomer obtained by Wittig reaction. J Lumin 145:752–759Google Scholar
  44. 44.
    Vishnumurthy KA, Sunitha MS, Philip R, Adhikari AV (2011) New diphenylamine-based donor–acceptor-type conjugated polymers as potential photonic materials. React Funct Polym 71(12):1119–1128Google Scholar
  45. 45.
    Upadhyay A, Karpagam S (2017) Synthesis and photo physical properties of carbazole based quinoxaline conjugated polymer for fluorescent detection of Ni2+. Dyes Pigm 139:50–64Google Scholar
  46. 46.
    Ammar KB, Guergouri M, Mosbah S, Bencharif L (2015) The synthesis, physicochemcal properties and electrochemical polymerization of fluorene-based derivatives as precursors for conjugated polymers. Tetrahedron Lett 56:2574–2578Google Scholar
  47. 47.
    Huo L, He C, Han M, Zhou E, Li Y (2007) Alternating copolymers of electron-rich arylamine and electron-deficient 2, 1, 3-benzothiadiazole: synthesis, characterization and photovoltaic properties. J Polym Sci Part A Polym Chem 45(17):3861–3871Google Scholar
  48. 48.
    Casey A, Ashraf RS, Fei Z, Heeney M (2014) Thioalkyl-substituted benzothiadiazole acceptors: copolymerization with carbazole affords polymers with large stokes shifts and high solar cell voltages. Macromolecules 47(7):2279–2288Google Scholar
  49. 49.
    Casey A, Han Y, Fei Z, White AJ, Anthopoulos TD, Heeney M (2015) Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers. J Mater Chem C 3(2):265–275Google Scholar
  50. 50.
    Mikroyannidis JA, Stylianakis MM, Suresh P, Balraju P, Sharma GD (2009) Low band gap vinylene compounds with triphenylamine and benzothiadiazole segments for use in photovoltaic cells. Org Electron 10(7):1320–1333Google Scholar
  51. 51.
    Ke L, Chen P, Kumar RS, Burden AP, Chua SJ (2006) Indium-tin-oxide-free organic light-emitting device. IEEE Trans Electron Devices 53(6):1483–1486Google Scholar
  52. 52.
    Moore W, Silver M (1960) Generation of free carriers in photoconducting anthracene. I. J Chem Phys 33(6):1671–1676Google Scholar
  53. 53.
    Ranjan S, Balaji S, Panella RA, Ydstie BE (2011) Silicon solar cell production. Comput Chem Eng 35(8):1439–1453Google Scholar
  54. 54.
    Yang X, Loos J, Veenstra SC, Verhees WJ, Wienk MM, Kroon JM, Janssen RA (2005) Nanoscale morphology of high-performance polymer solar cells. Nano Lett 5(4):579–583PubMedGoogle Scholar
  55. 55.
    Krebs FC, Norrman K (2007) Analysis of the failure mechanism for a stable organic photovoltaic during 10,000 h of testing. Prog Photovoltaics Res Appl 15(8):697–712Google Scholar
  56. 56.
    Gunes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107(4):1324–1338PubMedGoogle Scholar
  57. 57.
    Yu G, Heeger AJ (1995) Charge separation and photovoltaic conversion in polymer composites with internal donor/acceptor heterojunctions. J Appl Phys 78(7):4510–4515Google Scholar
  58. 58.
    Cui C, Wong W-Y, Li Y (2014) Improvement of open-circuit voltage and photovoltaic properties of 2D-conjugated polymers by alkylthio substitution. Energy Environ Sci 7:2276–2284Google Scholar
  59. 59.
    Cui C, He Z, Wu Y, Cheng X, Wu H, Li Y, Cao Y, Wong W-Y (2016) High-performance polymer solar cells based on a 2D-conjugated polymer with an alkylthio side-chain. Energy Environ Sci 9:885–891Google Scholar
  60. 60.
    Yang H, Wu Y, Zou Y, Dong Y, Yuan J, Cui C, Li Y (2018) A new polymer donor for efficient polymer solar cells: simultaneously realizing high short-circuit current density and transparency. J Mater Chem A 6:14700–14708Google Scholar
  61. 61.
    Guo B, Li W, Luo G, Guo X, Yao H, Zhang M, Hou J, Li Y, Wong W-Y (2018) Exceeding 14% efficiency for solution-processed tandem organic solar cels combining fullerene and nonfullerene-based subcells with complementary absorption. ACS Energy Lett 3:2566–2572Google Scholar
  62. 62.
    Grisorio R, Allegretta G, Romanazzi G, Suranna GP, Mastrorilli P, Mazzeo M, Gigli G (2012) An insight into the potential of random poly(heteroarylene–vinylene)s as donor materials in bulk heterojunction solar cells. Macromolecules 45(16):6396–6404Google Scholar
  63. 63.
    Liu D, Sun L, Du Z, Xiao M, Gu C, Wang T, Yang R (2014) Benzothiadiazole—an excellent acceptor for indacenodithiophene based polymer solar cells. RSC Adv 4(71):37934–37940Google Scholar
  64. 64.
    Guo X, Baumgarten M, Mullen K (2013) Designing π-conjugated polymers for organic electronics. Prog Polym Sci 38(12):1832–1908Google Scholar
  65. 65.
    Huang YQ, Liu XF, Fan QL, Wang L, Song S, Wang LH, Huang W (2009) Tuning backbones and side-chains of cationic conjugated polymers for optical signal amplification of fluorescent DNA detection. Biosens Bioelectron 24(10):2973–2978PubMedGoogle Scholar
  66. 66.
    Hu Y, Xiao Y, Huang H, Yin D, Xiao X, Tan W (2011) An anion-conjugated polyelectrolyte designed for the selective and sensitive detection of silver (I). Chem Asian J 6(6):1500–1504PubMedGoogle Scholar
  67. 67.
    Jeong SH, Lee JY, Lim B, Lee J, Noh YY (2017) Diketopyrrolopyrrole-based conjugated polymer for printed organic field-effect transistors and gas sensors. Dyes Pigm 140:244–249Google Scholar
  68. 68.
    Kane-Maguire LAP, Wallace GG (2001) Communicating with the building blocks of life using organic electronic conductors. Synth Met 119(1):39–42Google Scholar
  69. 69.
    Riul A, Soto AG, Mello SV, Bone S, Taylor DM, Mattoso LHC (2003) An electronic tongue using polypyrrole and polyaniline. Synth Met 132(2):109–116Google Scholar
  70. 70.
    Emre FB, Ekiz F, Balan A, Emre S, Timur S, Toppare L (2011) Conducting polymers with benzothiadiazole and benzoselenadiazole units for biosensor applications. Sens Actuators B Chem 158(1):117–123Google Scholar
  71. 71.
    Ma F, Shi W, Mi H, Luo J, Lei Y, Tian Y (2013) Triphenylamine-based conjugated polymer/I complex as turn-on optical probe for mercury (II) ion. Sens Actuators B Chem 182:782–788Google Scholar
  72. 72.
    Levesque I, Leclerc M (1996) Ionochromic and thermochromic phenomena in a regioregular polythiophene derivative bearing oligo (oxyethylene) side chains. Chem Mater 8(12):2843–2849Google Scholar
  73. 73.
    Fan LJ, Zhang Y, Murphy CB, Angell SE, Parker MF, Flynn BR, Jones WE Jr (2009) Fluorescent conjugated polymer molecular wire chemosensors for transition metal ion recognition and signalling. Coord Chem Rev 253(3–4):410–422Google Scholar
  74. 74.
    Boutagy J, Thomas R (1974) Olefin synthesis with organic phosphonate carbanions. Chem Rev 74(1):87–99Google Scholar
  75. 75.
    Cui W, Wang L, Xiang G, Zhou L, An X, Cao D (2015) A colorimetric and fluorescence “turn-off” chemosensor for the detection of silver ion based on a conjugated polymer containing 2, 3-di(pyridin-2-yl) quinoxaline. Sens Actuators B Chem 207:281–290Google Scholar
  76. 76.
    Rurack K, Kollmannsberger M, Resch-Genger U, Daub J (2000) A selective and sensitive fluoroionophore for HgII, AgI, and CuII with virtually decoupled fluorophore and receptor units. J Am Chem Soc 122(5):968–969Google Scholar
  77. 77.
    Fan LJ, Jones WE (2006) A highly selective and sensitive inorganic/organic hybrid polymer fluorescence “turn-on” chemosensory system for iron cations. J Am Chem Soc 128(21):6784–6785PubMedPubMedCentralGoogle Scholar
  78. 78.
    Shi W, Ma F, Xie Z (2015) Sulfur-containing, triphenylamine-based red-emitting conjugated polymer/I assembly as turn-on optical probe for mercury (II) ion. Sens Actuators B Chem 220:600–606Google Scholar
  79. 79.
    Feng L, Deng Y, Wang X, Liu M (2017) Polymer fluorescent probe for Hg(II) with thiophene, benzothiazole and quinoline groups. Sens Actuators B Chem 245:441–447Google Scholar
  80. 80.
    Pavase TR, Lin H, Li Z (2015) Rapid detection methodology for inorganic mercury (Hg2+) in seafood samples using conjugated polymer (1,4-bis-(8-(4-phenylthiazole-2-thiol)-octyloxy)-benzene) (PPT) by colorimetric and fluorescence spectroscopy. Sens Actuators B Chem 220:406–413Google Scholar

Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Department of Chemistry, School of Advanced ScienceVIT UniversityVelloreIndia
  2. 2.Department of Inorganic ChemistryUniversity of MadrasChennaiIndia

Personalised recommendations