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Polymer Bulletin

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01.05.2020 | Original Paper

Tuning of electronic properties of novel donor–acceptor polymers containing oligothiophenes with electron-withdrawing ester groups

verfasst von: Ichiro Imae, Naofumi Tada, Yutaka Harima

Erschienen in: Polymer Bulletin | Ausgabe 5/2021

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Abstract

To investigate the substituent effects introduced into oligothiophene units, a series of novel donor–acceptor conjugated polymers containing ester-substituted oligothiophenes were synthesized by the direct C–H arylation polycondensation of bis(ester-substituted thienyl)benzothiadiazole and dibromo-substituted oligothiophenes. The ultraviolet–visible absorption spectra of three polymers showed two absorption bands in the visible light wavelength region, ascribed to π–π* transition and the intramolecular charge transfer bands. The oxidation potentials of the polymers exhibited a negative shift with an increase in the chain length of the oligothiophene units. By comparing these polymers with alkyl-substituted analogues, it was found that the introduction of electron-withdrawing ester groups induced a negative shift in the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels and affected the LUMO rather than the HOMO energy levels. As a preliminary experiment, organic photovoltaic cells using these polymers were prepared, and their photoelectric conversion characteristics were investigated in relation to their chemical structures.

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Heeger AJ (2010) Semiconducting polymers: the third generation. Chem Soc Rev 39:2354–2371. https://doi.org/10.1039/b914956mCrossRefPubMed

Bujak P, Kulszewicz-Bajer I, Zagorska M, Maurel V, Wielgus I, Pron A (2013) Polymers for electronics and spintronics. Chem Soc Rev 42:8895–8999. https://doi.org/10.1039/c3cs60257eCrossRefPubMed

Marszalek T, Li M, Pisula W (2016) Design directed self-assembly of donor–acceptor polymers. Chem Commun 52:10938–10947. https://doi.org/10.1039/c6cc04523eCrossRef

van Mullekom HAM, Vekemans JAJM, Havinga EE, Meijer EW (2001) Developments in the chemistry and band gap engineering of donor–acceptor substituted conjugated polymers. Mater Sci Eng R 32:1–40. https://doi.org/10.1016/S0927-796X(00)00029-2CrossRef

Beaujuge PM, Amb CM, Reynolds JR (2010) Spectral engineering in π-conjugated polymers with intramolecular donor–acceptor interactions. Acc Chem Res 43:1396–1407. https://doi.org/10.1021/ar100043uCrossRefPubMed

Lv X, Li W, Ouyang M, Zhang Y, Wright DS, Zhang C (2017) Polymeric electrochromic materials with donor–acceptor structures. J Mater Chem C 5:12–28. https://doi.org/10.1039/c6tc04002kCrossRef

Fabian J (1992) Near-infrared absorbing dyes. Chem Rev 92:1197–1226. https://doi.org/10.1021/cr00014a003CrossRef

Pu KY, Liu B (2009) Optimizing the cationic conjugated polymer-sensitized fluorescent signal of dye labeled oligonucleotide for biosensor applications. Biosens Bioelectron 24:1067–1073. https://doi.org/10.1016/j.bios.2008.07.029CrossRefPubMed

Lee K, Povlich LK, Kim J (2010) Recent advances in fluorescent and colorimetric conjugated polymer-based biosensors. Analyst 135:2179–2189. https://doi.org/10.1039/c0an00239aCrossRefPubMed

10.

Cheng L, Wang C, Feng L, Yang K, Liu Z (2014) Functional nanomaterials for phototherapies of cancer. Chem Rev 114:10869–10939. https://doi.org/10.1021/cr400532zCrossRefPubMed

11.

Song X, Chen Q, Liu Z (2015) Recent advances in the development of organic photothermal nano-agents. Nano Res 8:340–354. https://doi.org/10.1007/s12274-014-0620-yCrossRef

12.

Held M, Zakharko Y, Wang M, Jakubka F, Gannott F, Rumer JW, Ashraf RS, McCulloch I, Zaumseil J (2016) Photo- and electroluminescence of ambipolar, high-mobility, donor–acceptor polymers. Org Electron 32:220–227. https://doi.org/10.1016/j.orgel.2016.02.030CrossRef

13.

Crossley DL, Urbano L, Neumann R, Bourke S, Jones J, Dailey LA, Green M, Humphries MJ, King SM, Turner ML, Ingleson MJ (2017) Post-polymerization C−H borylation of donor−acceptor materials gives highly efficient solid state near-infrared emitters for near-IR-OLEDs and effective biological imaging. ACS Appl Mater Int 9:28243–28249. https://doi.org/10.1021/acsami.7b08473CrossRef

14.

Yeh YM, Huang CH, Peng SH, Chang CC, Hsu CS (2019) Synthesis of novel conjugated polymers based on benzo[1,2-d:4,5-d′]-bis([1,2,3]triazole) for applications in organic field-effect transistors. Polym Chem 10:1471–1479. https://doi.org/10.1039/c8py01526kCrossRef

15.

Zhang ZG, Wang J (2012) Structures and properties of conjugated donor–acceptor copolymers for solar cell applications. J Mater Chem 22:4178–4187. https://doi.org/10.1039/c2jm14951fCrossRef

16.

Liu C, Wang K, Gong X, Heeger AJ (2016) Low bandgap semiconducting polymers for polymeric photovoltaics. Chem Soc Rev 45:4825–4846. https://doi.org/10.1039/c5cs00650cCrossRefPubMed

17.

Benten H, Mori D, Ohkita H, Ito S (2016) Recent research progress of polymer donor/polymer acceptor blend solar cells. J Mater Chem A 4:5340–5365. https://doi.org/10.1039/c5ta10759hCrossRef

18.

Bäuerle P (1992) End-capped oligothiophenes-new model compounds for polythiophenes. Adv Mater 4:102–107. https://doi.org/10.1002/adma.19920040209CrossRef

19.

Bäuerle P (1998) Oligothiophenes. In: Müllen K, Wegner G (eds) Electronic materials: the oligomer approach. Wiley-VCH, Weinheim, pp 105–197. https://doi.org/10.1002/9783527603220.ch2CrossRef

20.

McCullough RD (1998) The chemistry of conducting polythiophenes. Adv Mater 10:93–116. https://doi.org/10.1002/(SICI)1521-4095(199801)10:2%3c93:AID-ADMA93%3e3.0.CO;2-FCrossRef

21.

Roncali J (1999) Electrogenerated functional conjugated polymers as advanced electrode materials. J Mater Chem 9:1875–1893. https://doi.org/10.1039/A902747ECrossRef

22.

Fichou D (2000) Structural order in conjugated oligothiophenes and its implications on opto-electronic devices. J Mater Chem 10:571–588. https://doi.org/10.1039/A908312JCrossRef

23.

Turbiez M, Frère P, Allain M, Videlot C, Ackermann J, Roncali J (2005) Design of organic semiconductors: tuning the electronic properties of π-conjugated oligothiophenes with the 3,4-ethylenedioxythiophene (EDOT) building block. Chem Eur J 11:3742–3752. https://doi.org/10.1002/chem.200401058CrossRefPubMed

24.

Imae I, Imabayashi S, Komaguchi K, Tan Z, Ooyama Y, Harima Y (2014) Synthesis and electrical properties of novel oligothiophenes partially containing 3,4-ethylenedioxythiophenes. RSC Adv 4:2501–2508. https://doi.org/10.1039/c3ra44129fCrossRef

25.

Imae I, Sagawa H, Harima Y (2018) Fine-tuning of electronic properties in donor–acceptor conjugated polymers based on oligothiophenes. Jpn J Appl Phys 57:03EJ01. https://doi.org/10.7567/JJAP.57.03EJ01CrossRef

26.

Imae I, Tada N, Harima Y (2019) Synthesis and properties of donor–acceptor-type polymers comprising alkoxy-substituted bithiophene units. J Photopolym Sci Technol 32:585–592. https://doi.org/10.2494/photopolymer.32.585CrossRef

27.

Imae I, Kumano M, Harima Y (2019) Molecular properties of thiophene-based donor–acceptor–donor small molecules with well-defined structures. Sci Adv Mater 11:792–799. https://doi.org/10.1166/sam.2019.3507CrossRef

28.

Kellogg RM, Schaap AP, Wynberg H (1969) Bromination, deuteration, and lithiation of the dithienyls. J Org Chem 34:343–346. https://doi.org/10.1021/jo01254a019CrossRef

29.

Bäuerle P, Würthner F, Götz G, Effenberger F (1993) Selective synthesis of α-substituted oligothiophenes. Synthesis 1993:1099–1103. https://doi.org/10.1055/s-1993-26009CrossRef

30.

Imae I, Nawa K, Ohsedo Y, Noma N, Shirota Y (1997) Synthesis of a novel family of electrochemically-doped vinyl polymers containing pendant oligothiophenes and their electrical and electrochromic properties. Macromolecules 30:380–386. https://doi.org/10.1021/ma961250wCrossRef

31.

Wang Y, Michinobu T (2016) Benzothiadiazole and its π-extended, heteroannulated derivatives: useful acceptor building blocks for high-performance donor–acceptor polymers in organic electronics. J Mater Chem C 4:6200–6214. https://doi.org/10.1039/c6tc01860bCrossRef

32.

Pati PB (2016) Benzazole (B, N, O, S, Se and Te) based D–A–D type oligomers: switch from electropolymerization to structural aspect. Org Electron 38:97–106. https://doi.org/10.1016/j.orgel.2016.07.035CrossRef

33.

Tan SE, Sarjadi MS (2017) The recent development of carbazole-, benzothiadiazole-, and isoindigo-based copolymers for solar cells application: a review. Polym Sci Ser B Polym Chem 59:479–496. https://doi.org/10.1134/S1560090417050141CrossRef

34.

Li M, An C, Pisula W, Müllen K (2018) Cyclopentadithiophene−benzothiadiazole donor−acceptor polymers as prototypical semiconductors for high-performance field-effect transistors. Acc Chem Res 51:1196–1205. https://doi.org/10.1021/acs.accounts.8b00025CrossRefPubMed

35.

Borghese A, Geldhof G, Antoine L (2006) Direct C–H arylation of 3-methoxythiophene catalyzed by Pd. Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives. Tetrahedron Lett 47:9249–9252. https://doi.org/10.1016/j.tetlet.2006.10.130CrossRef

36.

Ishiyama T, Sato K, Nishio Y, Saiki T, Miyaura N (2005) Regioselective aromatic C–H silylation of five-membered heteroarenes with fluorodisilanes catalyzed by iridium(I) complexes. Chem Commun 41:5065–5067. https://doi.org/10.1039/b511171dCrossRef

37.

Lim E, Lee S, Lee KK, Kang IN, Moon SJ, Kong HY, Katz HE (2012) Solution-processable oligothiophenes with solubilizing β-alkyl groups for organic photovoltaic cells. Sol Energy Mater Sol Cells 107:165–174. https://doi.org/10.1016/j.solmat.2012.07.005CrossRef

38.

Shirota Y (2000) Organic materials for electronic and optoelectronic devices. J Mater Chem 10:1–25. https://doi.org/10.1039/A908130ECrossRef

39.

Shirota Y (2005) Photo- and electroactive amorphous molecular materials—molecular design, syntheses, reactions, properties, and applications. J Mater Chem 15:75–93. https://doi.org/10.1039/B413819HCrossRef

40.

Chen J, Liao Q, Wang G, Yan Z, Wang H, Wang Y, Zhang X, Tang Y, Facchetti A, Marks TJ, Guo X (2018) Enhancing polymer photovoltaic performance via optimized intramolecular ester-based noncovalent sulfur···oxygen interactions. Macromolecules 51:3874–3885. https://doi.org/10.1021/acs.macromol.8b00161CrossRef

41.

Yue W, Zhao Y, Tian H, Song D, Xie Z, Yan D, Geng Y, Wang F (2009) Poly(oligothiophene-alt-benzothiadiazole)s: tuning the structures of oligothiophene units toward high-mobility “black” conjugated polymers. Macromolecules 42:6510–6518. https://doi.org/10.1021/ma900906tCrossRef

42.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision D.01. Gaussian Inc., Wallingford

43.

Scharber MC, Mühlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CJ (2006) Design rules for donors in bulk-heterojunction solar cells—towards 10% energy-conversion efficiency. Adv Mater 18:789–794. https://doi.org/10.1002/adma.200501717CrossRef

44.

Lee JK, Ma WL, Brabec CJ, Yuen J, Moon JS, Kim JY, Lee K, Bazan GC, Heeger AJ (2008) Processing additives for improved efficiency from bulk heterojunction solar cells. J Am Chem Soc 130:3619–3623. https://doi.org/10.1021/ja710079wCrossRefPubMed

Titel: Tuning of electronic properties of novel donor–acceptor polymers containing oligothiophenes with electron-withdrawing ester groups
verfasst von: Ichiro Imae
Naofumi Tada
Yutaka Harima
Publikationsdatum: 01.05.2020
Verlag: Springer Berlin Heidelberg
Erschienen in: Polymer Bulletin / Ausgabe 5/2021
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-020-03212-5

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