Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (<italic style="font-style: italic">E</italic>)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers

Kai Guo; Yu Jiang; Ying Sui; Yun-Feng Deng; Yan-Hou Geng

doi:10.1007/s10118-019-2277-1

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Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers

ARTICLE | Updated：2021-02-18

- Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers
- Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers
- Chinese Journal of Polymer Science 2019年37卷第11期页码：1099-1104
- Affiliations：
  
  a.School of Materials Science and Engineering, Tianjin University, Tianjin 300072, China
  b.State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  c.Tianjin Key Laboratory of Molecular Optoelectronic Science, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
- Author bio：
  
  yunfeng.deng@tju.edu.cn (Y.F.D.)
  yanhou.geng@tju.edu.cn (Y.H.G.)
- Funds：
  
  This work was financially supported by the National Key R&D Program of “Strategic Advanced Electronic Materials” (No. 2016YFB0401101) of the Chinese Ministry of Science and Technology and the National Natural Science Foundation of China (No. 51333006).
- DOI：10.1007/s10118-019-2277-1
  中图分类号：
- 收稿：2019-03-11，
  
  修回：2019-4-15，
  
  录用：2019-4-18，
  
  网络首发：2019-06-17，
  
  纸质出版：2019-11
- Accepted：
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Guo, K.; Jiang, Y.; Sui, Y.; Deng, Y. F.; Geng, Y. H. Dimethylacetamide-promoted direct arylation polycondensation of 6,6′-dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward high molecular weight n-type conjugated polymers. Chinese J. Polym. Sci. 2019, 37, 1099–1104.

Kai Guo, Yu Jiang, Ying Sui, et al. Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers[J]. Chinese Journal of Polymer Science, 2019, 37(11): 1099-1104. DOI: 10.1007/s10118-019-2277-1.
Guo, K.; Jiang, Y.; Sui, Y.; Deng, Y. F.; Geng, Y. H. Dimethylacetamide-promoted direct arylation polycondensation of 6,6′-dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward high molecular weight n-type conjugated polymers. Chinese J. Polym. Sci. 2019, 37, 1099–1104. DOI： 10.1007/s10118-019-2277-1.

Kai Guo, Yu Jiang, Ying Sui, et al. Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers[J]. Chinese Journal of Polymer Science, 2019, 37(11): 1099-1104. DOI: 10.1007/s10118-019-2277-1. DOI：

摘要

Abstract

A highly efficient and eco-friendly protocol for the synthesis of an alternating copolymer poly(7

7′-diazaisoindigo-

alt

)-1

2-bis(3

4-difluorothien-2-yl)ethene) (PAIID-4FTVT)

via

direct arylation polycondensation (DArP) is presented. Through detailed study

we found that the inhibitory effect of 7

7′-diazaisoindigo on DArP stemmed from the coordination of N atom with catalyst can be overcome by using dimethylacetamide (DMAc) as the co-solvent. Thus

PAIID-4FTVT with number-average molecular weight (

)

100 kDa was synthesized

via

DArP by optimizing the content of DMAc. Matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectroscopy revealed that PAIID-4FTVT was defect-free. Top gate and bottom contact (TG/BC) organic thin-film transistors (OTFTs) were fabricated to characterize the semiconducting properties of the polymers. PAIID-4FTVT displayed unipolar n-type characteristics with the electron mobility (

) strongly dependent on

. The highest

up to 0.25 cm

·V

–1

·s

–1

was achieved with the high molecular weight sample.

关键词

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references

Rudenko, A. E.; Thompson, B. C . Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure . J. Polym. Sci., Part A: Polym. Chem. , 2015 . 53 135 - 147 . DOI: 10.1002/pola.27279 http://doi.org/10.1002/pola.27279 .

Pouliot, J. R.; Grenier, F.; Blaskovits, J. T.; Beaupré, S.; Leclerc, M . Direct (hetero)arylation polymerization: Simplicity for conjugated polymer synthesis . Chem. Rev. , 2016 . 116 14225 - 14274 . DOI: 10.1021/acs.chemrev.6b00498 http://doi.org/10.1021/acs.chemrev.6b00498 .

Bura, T.; Blaskovits, J. T.; Leclerc, M . Direct (hetero)arylation polymerization: Trends and perspectives . J. Am. Chem. Soc. , 2016 . 138 10056 - 10071 . DOI: 10.1021/jacs.6b06237 http://doi.org/10.1021/jacs.6b06237 .

Bohra, H.; Wang, M . Direct C-H arylation: A " greener” approach towards facile synthesis of organic semiconducting molecules and polymers . J. Mater. Chem. A , 2017 . 5 11550 - 11571 . DOI: 10.1039/C7TA00617A http://doi.org/10.1039/C7TA00617A .

Wakioka, M.; Ozawa, F . Highly efficient catalysts for direct arylation polymerization (DArP) . Asian J. Org. Chem. , 2018 . 7 1206 - 1216 . DOI: 10.1002/ajoc.v7.7 http://doi.org/10.1002/ajoc.v7.7 .

Gao, Y.; Zhang, X.; Tian, H.; Zhang, J.; Yan, D.; Geng, Y.; Wang, F . High mobility ambipolar diketopyrrolopyrrole-based conjugated polymer synthesized via direct arylation polycondensation . Adv. Mater. , 2015 . 27 6753 - 6759 . DOI: 10.1002/adma.201502896 http://doi.org/10.1002/adma.201502896 .

Gao, Y.; Deng, Y.; Tian, H.; Zhang, J.; Yan, D.; Geng, Y.; Wang, F . Multifluorination toward high-mobility ambipolar and unipolar n-type donor-acceptor conjugated polymers based on isoindigo . Adv. Mater. , 2017 . 29 1606217 DOI: 10.1002/adma.201606217 http://doi.org/10.1002/adma.201606217 .

Song, H.; Deng, Y.; Gao, Y.; Jiang, Y.; Tian, H.; Yan, D.; Geng, Y.; Wang, F . Donor-acceptor conjugated polymers based on indacenodithiophene derivative bridged diketopyrrolopyrroles: Synthesis and semiconducting properties . Macromolecules , 2017 . 50 2344 - 2353 . DOI: 10.1021/acs.macromol.6b02781 http://doi.org/10.1021/acs.macromol.6b02781 .

Gao, Y.; Bai, J.; Sui, Y.; Han, Y.; Deng, Y.; Tian, H.; Geng, Y.; Wang, F . High mobility ambipolar diketopyrrolopyrrole-based conjugated polymers synthesized via direct arylation polycondensation: Influence of thiophene moieties and side chains . Macromolecules , 2018 . 51 8752 - 8760 . DOI: 10.1021/acs.macromol.8b01112 http://doi.org/10.1021/acs.macromol.8b01112 .

Guo, K.; Bai, J.; Jiang, Y.; Wang, Z.; Sui, Y.; Deng, Y.; Han, Y.; Tian, H.; Geng, Y . Diketopyrrolopyrrole-based conjugated polymers synthesized via direct arylation polycondensation for high mobility pure n -channel organic field-effect transistors . Adv. Funct. Mater. , 2018 . 1801097 .

Huang, J.; Mao, Z.; Chen, Z.; Gao, D.; Wei, C.; Zhang, W.; Yu, G . Diazaisoindigo-based polymers with high-performance charge-transport properties: From computational screening to experimental characterization . Chem. Mater. , 2016 . 28 2209 - 2218 . DOI: 10.1021/acs.chemmater.6b00154 http://doi.org/10.1021/acs.chemmater.6b00154 .

Randell, N. M.; Kelly, T. L . Recent advances in isoindigo-inspired organic semiconductors . Chem. Rec. , 2018 . DOI: 10.1002/tcr.201800135 DOI: 10.1002/tcr.201800135 http://doi.org/10.1002/tcr.201800135 .

Wagaw, S.; Buchwald, S. L . The synthesis of aminopyridines: A method employing palladium-catalyzed carbon-nitrogen bond formation . J. Org. Chem. , 1996 . 61 7240 - 7241 . DOI: 10.1021/jo9612739 http://doi.org/10.1021/jo9612739 .

Zhao, Y.; Nett, A. J.; McNeil, A. J.; Zimmerman, P. M . Computational mechanism for initiation and growth of poly(3-hexylthiophene) using palladium N -heterocyclic carbene precatalysts . Macromolecules , 2016 . 49 7632 - 7641 . DOI: 10.1021/acs.macromol.6b01648 http://doi.org/10.1021/acs.macromol.6b01648 .

Shi, Y.; Guo, H.; Qin, M.; Wang, Y.; Zhao, J.; Sun, H.; Wang, H.; Wang, Y.; Zhou, X.; Facchetti, A.; Lu, X. H.; Zhou, M.; Guo, X . Imide-functionalized thiazole-based polymer semiconductors: Synthesis, structure-property correlations, charge carrier polarity, and thin-film transistor performance . Chem. Mater. , 2018 . 30 7988 - 8001 . DOI: 10.1021/acs.chemmater.8b03670 http://doi.org/10.1021/acs.chemmater.8b03670 .

Lee, J. A.; Luscombe, C. K . Dual-catalytic Ag-Pd system for direct arylation polymerization to synthesize poly(3-hexylthiophene) . ACS Macro Lett. , 2018 . 7 767 - 771 . DOI: 10.1021/acsmacrolett.8b00429 http://doi.org/10.1021/acsmacrolett.8b00429 .

Lu, W.; Kuwabara, J.; Kanbara, T . Synthesis of π -conjugated polymer consisting of pyrrole and fluorene units by Ru-catalyzed site-selective direct arylation polycondensation . Macromol. Rapid Commun. , 2013 . 34 1151 - 1156 . DOI: 10.1002/marc.201300303 http://doi.org/10.1002/marc.201300303 .

Matsidik, R.; Komber, H.; Luzio, A.; Caironi, M.; Sommer, M . Defect-free naphthalene diimide bithiophene copolymers with controlled molar mass and high performance via direct arylation polycondensation . J. Am. Chem. Soc. , 2015 . 137 6705 - 6711 . DOI: 10.1021/jacs.5b03355 http://doi.org/10.1021/jacs.5b03355 .

Lombeck, F.; Komber, H.; Gorelsky, S. I.; Sommer, M . Identifying homocouplings as critical side reactions in direct arylation polycondensation . ACS Macro Lett. , 2014 . 3 819 - 823 . DOI: 10.1021/mz5004147 http://doi.org/10.1021/mz5004147 .

Wang, Q.; Qu, Y.; Tian, H.; Geng, Y.; Wang, F . Iterative binomial synthesis of monodisperse polyfluorenes up to 64-mers and their chain-length-dependent properties . Macromolecules , 2011 . 44 1256 - 1260 . DOI: 10.1021/ma102954h http://doi.org/10.1021/ma102954h .

Aldrich, T. J.; Dudnik, A. S.; Eastham, N. D.; Manley, E. F.; Chen, L. X.; Chang, R. P.; Melkonyan, F. S.; Facchetti, A.; Marks, T. J . Suppressing defect formation pathways in the direct C―H arylation polymerization of photovoltaic copolymers . Macromolecules , 2018 . 51 9140 - 9155 . DOI: 10.1021/acs.macromol.8b02297 http://doi.org/10.1021/acs.macromol.8b02297 .

Bartelt, J. A.; Douglas, J. D.; Mateker, W. R.; Labban, A. E.; Tassone, C. J.; Toney, M. F.; Fréchet, J. M.; Beaujuge, P. M.; McGehee, M. D . Controlling solution-phase polymer aggregation with molecular weight and solvent additives to optimize polymer-fullerene bulk heterojunction solar cells . Adv. Energy Mater. , 2014 . 4 1301733 DOI: 10.1002/aenm.201301733 http://doi.org/10.1002/aenm.201301733 .

Xiao, Z.; Sun, K.; Subbiah, J.; Qin, T.; Lu, S.; Purushothaman, B.; Jones, D. J.; Holmes, A. B.; Wong, W. W . Effect of molecular weight on the properties and organic solar cell device performance of a donor-acceptor conjugated polymer . Polym. Chem. , 2015 . 6 2312 - 2318 . DOI: 10.1039/C4PY01631A http://doi.org/10.1039/C4PY01631A .

Vezie, M. S.; Few, S.; Meager, I.; Pieridou, G.; Dörling, B.; Ashraf, R. S.; Goñi, A. R.; Bronstein, H.; McCulloch, I.; Hayes, S. C.; Campoy-Quiles, M.; Nelson, J . Exploring the origin of high optical absorption in conjugated polymers . Nat. Mater. , 2016 . 15 746 DOI: 10.1038/nmat4645 http://doi.org/10.1038/nmat4645 .

Li, J.; Zhao, Y.; Tan, H. S.; Guo, Y.; Di, C. A.; Yu, G.; Liu, Y.; Lin, M.; Lim, S. H.; Zhou, Y.; Su, H.; S. Ong, B . A stable solution-processed polymer semiconductor with record high-mobility for printed transistors . Sci. Rep. , 2012 . 2 754 DOI: 10.1038/srep00754 http://doi.org/10.1038/srep00754 .

Gasperini, A.; Sivula, K . Effects of molecular weight on microstructure and carrier transport in a semicrystalline poly(thieno)-thiophene . Macromolecules , 2013 . 46 9349 - 9358 . DOI: 10.1021/ma402027v http://doi.org/10.1021/ma402027v .

Tong, M.; Cho, S.; Rogers, J. T.; Schmidt, K.; Hsu, B. B.; Moses, D.; Coffin, R. C.; Kramer, E. J.; Bazan, G. C.; Heeger, A. J . Higher molecular weight leads to improved photoresponsivity, charge transport and interfacial ordering in a narrow bandgap semiconducting polymer . Adv. Funct. Mater. , 2010 . 20 3959 - 3965 . DOI: 10.1002/adfm.201001271 http://doi.org/10.1002/adfm.201001271 .

Tsao, H. N.; Cho, D. M.; Park, I.; Hansen, M. R.; Mavrinskiy, A.; Yoon, D. Y.; Graf, R.; Pisula, W.; Spiess, H. W.; Müllen, K . Ultrahigh mobility in polymer field-effect transistors by design . J. Am. Chem. Soc. , 2011 . 133 2605 - 2612 . DOI: 10.1021/ja108861q http://doi.org/10.1021/ja108861q .

Zheng, Y. Q.; Yao, Z. F.; Lei, T.; Dou, J. H.; Yang, C. Y.; Zou, L.; Meng, X.; Ma, W.; Wang, J. Y.; Pei, J . Unraveling the solution-state supramolecular structures of donor-acceptor polymers and their influence on solid-state morphology and charge-transport properties . Adv. Mater. , 2017 . 29 1701072 DOI: 10.1002/adma.201701072 http://doi.org/10.1002/adma.201701072 .

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Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers

Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers

DOI：10.1007/s10118-019-2277-1

摘要

Abstract

关键词

Keywords

references