Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation

Qiang Zhang; Yue-Feng Li; Lu-Di Deng; Lin-Lin Zhao; Chen-Xi Li; Yan Lu

doi:10.1007/s10118-018-2116-9

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Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation

ARTICLE | Updated：2021-02-18

- Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation
- Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation
- Chinese Journal of Polymer Science 2018年36卷第9期页码：1019-1026
- Affiliations：
  
  a.Tianjin Key Laboratory for Photoelectric Materials and Devices, School of Materials Science & Engineering, Tianjin University of Technology, Tianjin 300384, China
  b.Key Laboratory of Functional Polymer Materials, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
- Author bio：
  
  zdianq2007@126.com (Q.Z.)
  luyan@tjut.edu.cn (Y.L.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21604063 and 51373122) and China Postdoctoral Science Foundation (No. 2016M591392).
- DOI：10.1007/s10118-018-2116-9
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Qiang Zhang, Yue-Feng Li, Lu-Di Deng, 等. Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation[J]. Chinese Journal of Polymer Science, 2018,36(9):1019-1026.

Qiang Zhang, Yue-Feng Li, Lu-Di Deng, et al. Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation[J]. Chinese Journal of Polymer Science, 2018,36(9):1019-1026.
Qiang Zhang, Yue-Feng Li, Lu-Di Deng, 等. Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation[J]. Chinese Journal of Polymer Science, 2018,36(9):1019-1026. DOI： 10.1007/s10118-018-2116-9.

Qiang Zhang, Yue-Feng Li, Lu-Di Deng, et al. Synthesis of Highly Regioregular, Head-to-Tail Coupled Poly(3-octylesterthiophene) via C―H/C―H Coupling Polycondensation[J]. Chinese Journal of Polymer Science, 2018,36(9):1019-1026. DOI： 10.1007/s10118-018-2116-9.

摘要

Abstract

Highly regioregular, head-to-tail coupled poly(3-octylesterthiophene) was synthesized by the Pd-catalysed oxidative C―H/C―H coupling polycondensation. The regioregularity of polymer products was confirmed by the ,1,H-NMR technique. Furthermore, the effects of various reaction factors including polymerization temperature, solvents and catalysts ,etc., on the yield, molecular weight and structural regioregularity of the resultant polymers were systematically studied. The optical, electrochemical and crystallization properties of the resultant P3OET with different HT regioregularities in solution and film state were studied by UV-Vis and fluorescent spectroscopy, cyclic voltammetry and X-ray diffraction (XRD), resepectively.

关键词

Keywords

C―H/C―H coupling polymerizationPd catalysed oxidativePoly(thiophene)s

references

Bujak, P.; Kulszewicz-Bajer, I.; Zagorska, M.; Maurel, V.; Wielgus, I.; Pron, A . Polymers for electronics and spintronics . Chem. Soc. Rev. , 2013 . 42 (23 ):8895 -8999 . DOI:10.1039/c3cs60257ehttp://doi.org/10.1039/c3cs60257e .

Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D . Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics . Chem. Rev. , 2011 . 112 (4 ):2208 -2267. .

Kim, D. H.; Lee, B. L.; Moon, H.; Kang, H. M.; Jeong, E. J.; Park, J. I.; Han, K. M.; Lee, S.; Yoo, B. W.; Koo, B. W.; Kim, J. Y.; Lee, W. H.; Cho, K.; Becerril, H. A.; Bao, Z . Liquid-crystalline semiconducting copolymers with intramolecular donor-acceptor building blocks for high-stability polymer transistors . J. Am. Chem. Soc. , 2009 . 131 (17 ):6124 -6132 . DOI:10.1021/ja8095569http://doi.org/10.1021/ja8095569 .

Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L . Stille polycondensation for synthesis of functional materials . Chem. Rev. , 2011 . 111 (3 ):1493 -1528 . DOI:10.1021/cr100320whttp://doi.org/10.1021/cr100320w .

Grimsdale, A. C.; Leok Chan, K.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B . Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices . Chem. Rev. , 2009 . 109 (3 ):897 -1091 . DOI:10.1021/cr000013vhttp://doi.org/10.1021/cr000013v .

Shirota, Y.; Kageyama, H . Charge carrier transporting molecular materials and their applications in devices . Chem. Rev. , 2007 . 107 (4 ):953 -1010 . DOI:10.1021/cr050143+http://doi.org/10.1021/cr050143+ .

Heeger, A . Semiconducting polymers: the third generation . Chem. Soc. Rev. , 2010 . 39 (7 ):2354 -2371 . DOI:10.1039/b914956mhttp://doi.org/10.1039/b914956m .

Armstrong, N. R.; Veneman, P. A.; Ratcliff, E.; Placencia, D.; Brumbach, M . Oxide contacts in organic photovoltaics: characterization and control of near-surface composition in indium-tin oxide (ITO) electrodes . Acc. Chem. Res. , 2009 . 42 (11 ):1748 -1757 . DOI:10.1021/ar900096fhttp://doi.org/10.1021/ar900096f .

Chen, Y.; Wan, X.; Long, G . High performance photovoltaic applications using solution-processed small molecules . Acc. Chem. Res. , 2013 . 46 (11 ):2645 -2655 . DOI:10.1021/ar400088chttp://doi.org/10.1021/ar400088c .

Lin, Y.; Fan, H.; Li, Y.; Zhan, X . Thiazole-based organic semiconductors for organic electronics . Adv. Mater. , 2012 . 24 (23 ):3087 -3106 . DOI:10.1002/adma.201200721http://doi.org/10.1002/adma.201200721 .

Chen, J.; Cao, Y . Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices . Acc. Chem. Res. , 2009 . 42 (11 ):1709 -1718 . DOI:10.1021/ar900061zhttp://doi.org/10.1021/ar900061z .

Murphy, A. R.; Fréchet, J. M. J . Organic semiconducting oligomers for use in thin film transistors . Chem. Rev. , 2007 . 107 (4 ):1066 -1096 . DOI:10.1021/cr0501386http://doi.org/10.1021/cr0501386 .

Cheng, D.; Li, Y.; Wang, J.; Sun, Y.; Jin, L.; Li, C.; Lu, Y . Fluorescence and colorimetric detection of ATP based on a strategy of self-promoting aggregation of a water-soluble polythiophene derivative . Chem. Commun. , 2015 . 51 (40 ):8544 -8546 . DOI:10.1039/C5CC01713Khttp://doi.org/10.1039/C5CC01713K .

Pomerantz, M.; Cheng, Y.; Kasim, R. K.; Elsenbaumer, R. L . Poly(alkyl thiophene-3-carboxylates). Synthesis, properties and electroluminescence studies of polythiophenes containing a carbonyl group directly attached to the ring . J. Mater. Chem. , 1999 . 9 (9 ):2155 -2163 . DOI:10.1039/a902504ihttp://doi.org/10.1039/a902504i .

Osaka, I.; McCullough, R. D . Advances in molecular design and synthesis of regioregular polythiophenes . Acc. Chem. Res. , 2008 . 41 (9 ):1202 -1214 . DOI:10.1021/ar800130shttp://doi.org/10.1021/ar800130s .

Osaka, I.; McCullough, R. D., Regioregular and regiosymmetric polythiophenes. In "Conjugated Polymer Synthesis", Wiley-VCH Verlag GmbH & Co. KGaA: 2010; p. 59–90.

Steyrleuthner, R.; Di Pietro, R.; Collins, B. A.; Polzer, F.; Himmelberger, S.; Schubert, M.; Chen, Z.; Zhang, S.; Salleo, A.; Ade, H.; Facchetti, A.; Neher, D . The role of regioregularity, crystallinity, and chain orientation on electron transport in a high-mobility n-type copolymer . J. Am. Chem. Soc. , 2014 . 136 (11 ):4245 -4256 . DOI:10.1021/ja4118736http://doi.org/10.1021/ja4118736 .

Woo, C. H.; Thompson, B. C.; Kim, B. J.; Toney, M. F.; Fréchet, J. M. J . The influence of poly(3-hexylthiophene) regioregularity on fullerene-composite solar cell performance . J. Am. Chem. Soc. , 2008 . 130 (48 ):16324 -16329 . DOI:10.1021/ja806493nhttp://doi.org/10.1021/ja806493n .

Chochos, C. L.; Choulis, S. A . How the structural deviations on the backbone of conjugated polymers influence their optoelectronic properties and photovoltaic performance . Prog. Polym. Sci. , 2011 . 36 (10 ):1326 -1414 . DOI:10.1016/j.progpolymsci.2011.04.003http://doi.org/10.1016/j.progpolymsci.2011.04.003 .

McCullough, R. D.; Lowe, R. D . Enhanced electrical conductivity in regioselectively synthesized poly(3-alkylthiophenes) . J. Chem. Soc., Chem. Commun. , 1992 . (1 ):70 -72 . DOI:10.1039/c39920000070http://doi.org/10.1039/c39920000070 .

Chen, T. A.; Rieke, R. D . The first regioregular head-to-tail poly(3-hexylthiophene-2,5-diyl) and a regiorandom isopolymer: nickel versus palladium catalysis of 2(5)-bromo-5(2)-(bromozincio)-3-hexylthiophene polymerization . J. Am. Chem. Soc. , 1992 . 114 (25 ):10087 -10088 . DOI:10.1021/ja00051a066http://doi.org/10.1021/ja00051a066 .

Loewe, R. S.; Khersonsky, S. M.; McCullough, R. D . A simple method to prepare head-to-tail coupled, regioregular poly(3-alkylthiophenes) using grignard metathesis . Adv. Mater. , 1999 . 11 (3 ):250 -253 . DOI:10.1002/(ISSN)1521-4095http://doi.org/10.1002/(ISSN)1521-4095 .

Khlyabich, P. P.; Burkhart, B.; Thompson, B. C . Compositional dependence of the open-circuit voltage in ternary blend bulk heterojunction solar cells based on two donor polymers . J. Am. Chem. Soc. , 2012 . 134 (22 ):9074 -9077 . DOI:10.1021/ja302935nhttp://doi.org/10.1021/ja302935n .

Iraqi, A.; W. Barker, G . Synthesis and characterisation of telechelic regioregular head-to-tail poly(3-alkylthiophenes) . J. Mater. Chem. , 1998 . 8 (1 ):25 -29 . DOI:10.1039/a706583chttp://doi.org/10.1039/a706583c .

Baek, M. J.; Lee, S. H.; Zong, K.; Lee, Y. S . Low band gap conjugated polymers consisting of alternating dodecyl thieno[3,4-b]thiophene-2-carboxylate and one or two thiophene rings: synthesis and photovoltaic property . Synth. Met. , 2010 . 160 (11-12 ):1197 -1203 . DOI:10.1016/j.synthmet.2010.03.008http://doi.org/10.1016/j.synthmet.2010.03.008 .

Mercier, L. G.; Leclerc, M . Direct (hetero)arylation: A new tool for polymer chemists . Acc. Chem. Res. , 2013 . 46 (7 ):1597 -1605 . DOI:10.1021/ar3003305http://doi.org/10.1021/ar3003305 .

Berrouard, P.; Najari, A.; Pron, A.; Gendron, D.; Morin, P. O.; Pouliot, J. R.; Veilleux, J.; Leclerc, M . Synthesis of 5-alkyl[3,4-c]thienopyrrole-4,6-dione-based polymers by direct heteroarylation . Angew. Chem. Int. Ed. , 2012 . 51 (9 ):2068 -2071 . DOI:10.1002/anie.201106411http://doi.org/10.1002/anie.201106411 .

Wang, Q.; Takita, R.; Kikuzaki, Y.; Ozawa, F . Palladium-catalyzed dehydrohalogenative polycondensation of 2-bromo-3-hexylthiophene: an efficient approach to head-to-tail poly(3-hexylthiophene) . J. Am. Chem. Soc. , 2010 . 132 (33 ):11420 -11421 . DOI:10.1021/ja105767zhttp://doi.org/10.1021/ja105767z .

Kuramochi, M.; Kuwabara, J.; Lu, W.; Kanbara, T . Direct arylation polycondensation of bithiazole derivatives with various acceptors . Macromolecules , 2014 . 47 (21 ):7378 -7385 . DOI:10.1021/ma5014397http://doi.org/10.1021/ma5014397 .

Huang, Q.; Qin, X.; Li, B.; Lan, J.; Guo, Q.; You, J . Cu-catalysed oxidative C―H/C―H coupling polymerisation of benzodiimidazoles: an efficient approach to regioregular polybenzodiimidazoles for blue-emitting materials . Chem. Commun. , 2014 . 50 (89 ):13739 -13741 . DOI:10.1039/C4CC06291Dhttp://doi.org/10.1039/C4CC06291D .

Zhang, Q.; Wan, X.; Lu, Y.; Li, Y.; Li, Y.; Li, C.; Wu, H.; Chen, Y . The synthesis of 5-alkyl[3,4-c]thienopyrrole-4,6-dione-based polymers using a Pd-catalyzed oxidative C―H/C―H homopolymerization reaction . Chem. Commun. , 2014 . 50 (83 ):12497 -12499 . DOI:10.1039/C4CC06284Ahttp://doi.org/10.1039/C4CC06284A .

Zhang, Q.; Li, Y.; Lu, Y.; Zhang, H.; Li, M.; Yang, Y.; Wang, J.; Chen, Y.; Li, C . Pd-catalysed oxidative C―H/C―H coupling polymerization for polythiazole-based derivatives . Polymer , 2015 . 68 (0 ):227 -233. .

Tsuchiya, K.; Ogino, K . Catalytic oxidative polymerization of thiophene derivatives . Polym. J. , 2013 . 45 (3 ):281 -286 . DOI:10.1038/pj.2012.146http://doi.org/10.1038/pj.2012.146 .

Hu, X.; Zuo, L.; Fu, W.; Larsen-Olsen, T. T.; Helgesen, M.; Bundgaard, E.; Hagemann, O.; Shi, M.; Krebs, F. C.; Chen, H . Incorporation of ester groups into low band-gap diketopyrrolopyrrole containing polymers for solar cell applications . J. Mater. Chem. , 2012 . 22 (31 ):15710 -15716 . DOI:10.1039/c2jm31700ahttp://doi.org/10.1039/c2jm31700a .

Sato, M.; Morii, H . Nuclear magnetic resonance studies on electrochemically prepared poly(3-dodecylthiophene) . Macromolecules , 1991 . 24 (5 ):1196 -1200 . DOI:10.1021/ma00005a035http://doi.org/10.1021/ma00005a035 .

Sato, M.; Shimizu, T.; Yamauchi, A . Electrochemical copolymerization of 3-dodecylthiophene and 3-methylthiophene . Makromol. Chem. , 1990 . 191 (2 ):313 -19 . DOI:10.1002/macp.1990.021910205http://doi.org/10.1002/macp.1990.021910205 .

Pomerantz, M.; Yang, H.; Cheng, Y . Poly(alkyl thiophene-3-carboxylates). Synthesis and characterization of polythiophenes with a carbonyl group directly attached to the ring . Macromolecules , 1995 . 28 (17 ):5706 -5708 . DOI:10.1021/ma00121a003http://doi.org/10.1021/ma00121a003 .

Gobalasingham, N. S.; Noh, S.; Thompson, B. C . Palladium-catalyzed oxidative direct arylation polymerization (Oxi-DArP) of an ester-functionalized thiophene . Polym. Chem. , 2016 . 7 (8 ):1623 -1631 . DOI:10.1039/C5PY01973Ghttp://doi.org/10.1039/C5PY01973G .

Forrest, J . 121. The Ullmann biaryl synthesis. Part V. The influence of ring substituents on the rate of self-condensation of an aryl halide . Journal of the Chemical Society (Resumed) , 1960 . 592 -594. .

Huggins, M . Dependence of polymer properties on temperature of polymerization . J. Am. Chem. Soc. , 1944 . 66 (11 ):1991 -1992 . DOI:10.1021/ja01239a513http://doi.org/10.1021/ja01239a513 .

Rudenko, A. E.; Wiley, C. A.; Tannaci, J. F.; Thompson, B. C . Optimization of direct arylation polymerization conditions for the synthesis of poly(3-hexylthiophene) . J. Polym. Sci., Part A: Polym. Chem. , 2013 . 51 (12 ):2660 -2668 . DOI:10.1002/pola.26655http://doi.org/10.1002/pola.26655 .

Zhang, Q.; Chang, M.; Lu, Y.; Sun, Y.; Li, C.; Yang, X.; Zhang, M.; Chen, Y . A direct C―H coupling method for preparing π-conjugated functional polymers with high regioregularity . Macromolecules , 2018 . 51 (2 ):379 -388 . DOI:10.1021/acs.macromol.7b02390http://doi.org/10.1021/acs.macromol.7b02390 .

Xi, P.; Yang, F.; Qin, S.; Zhao, D.; Lan, J.; Gao, G.; Hu, C.; You, J . Palladium(II)-catalyzed oxidative C―H/C―H cross-coupling of heteroarenes . J. Am. Chem. Soc. , 2010 . 132 (6 ):1822 -1824 . DOI:10.1021/ja909807fhttp://doi.org/10.1021/ja909807f .

Yao, S.; Beginn, U.; Gress, T.; Lysetska, M.; Würthner, F . Supramolecular polymerization and gel formation of bis(merocyanine) dyes driven by dipolar aggregation . J. Am. Chem. Soc. , 2004 . 126 (26 ):8336 -8348 . DOI:10.1021/ja0496367http://doi.org/10.1021/ja0496367 .

West, W.; Pearce, S . The dimeric state of cyanine dyes . J Phys. Chen. , 1965 . 69 (6 ):1894 -1903 . DOI:10.1021/j100890a019http://doi.org/10.1021/j100890a019 .

Yahav, G.; Haas, Y . Silicon tetrafluoride visible luminescence induced by high-power CO2 laser irradiation . Chem. Phys. Lett. , 1981 . 83 (3 ):493 -497 . DOI:10.1016/0009-2614(81)85508-Xhttp://doi.org/10.1016/0009-2614(81)85508-X .

Potai, R.; Traiphol, R . Control over the photophysical properties of nanoparticles of regioregular poly(3-octylthiophene) using various poor solvents . Synth. Met. , 2015 . 203 1 -9 . DOI:10.1016/j.synthmet.2015.02.005http://doi.org/10.1016/j.synthmet.2015.02.005 .

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