Facile synthesis of a narrow-bandgap strong-donor-alt-strong-acceptor copolymer of poly(5,6-difluorobenzo-[c][1,2,5]-thiadiazole-alt-5H-dithieno[3,2-b:2′,3′-d]pyran) via direct C-H arylation polymerization

被引：10
|
作者：
Efrem, Amsalu [1 ]
Wang, Kai [1 ]
Wang, Mingfeng [1 ]
机构：
[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, 62 Nanyang Dr, Singapore 637459, Singapore
来源：
DYES AND PIGMENTS | 2017年 / 145卷
关键词：
Benzothiadiazole; Conjugated polymer; Direct arylation polymerization; Organic electronics; CATALYZED DIRECT ARYLATION; CONJUGATED POLYMERS; SOLAR-CELLS; SEMICONDUCTING POLYMERS; DIRECT (HETERO)ARYLATION; ORGANIC SEMICONDUCTORS; DIRECT HETEROARYLATION; NAPHTHALENE DIIMIDE; POLYCONDENSATION; DESIGN;
D O I：
10.1016/j.dyepig.2017.05.040
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A narrow bandgap D-A conjugated polymer based on 5H-dithieno [3,2-b:2',3'-d]pyran alternating with 5,6-difluoro-2,1,3-benzothiadiazole (denoted as PDFI3T-alt-DTP) was synthesized via direct C-H arylation polymerization (DAP) as an atomically efficient protocol. The optimal reaction condition for the DAP gave the target polymers with moderate number-average molecular weights (M-n) using optimized catalytic condition of Pd2 (dba)3/(o-MeOPh)(3)P/PivOH/K2CO3 in o-xylene. UV-vis-NIR absorption spectra of the obtained polymers show the presence of aggregation and interchain interaction in thin films. H-1-NMR spectroscopic analysis indicates good C-H selectivity corresponding to an alternating strong-donor-alt strong -acceptor conjugated backbone. The hole mobility of the resulting polymers in a magnitude of 10(-4) cm(2)v(-1) S-1 was reached in bottom-gate top-contact field-effect transistors fabricated and tested under ambient conditions. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：331 / 338
页数：8
相关论文
共 20 条
  • [1] Solvent Annealing Effects in Dithieno[3,2-b:2′,3′-d]pyrrole-5,6Difluorobenzo[c][1,2,5]thiadiazole Small Molecule Donors for BulkHeterojunction Solar Cells
    Wang, Kai
    Azouz, Mehdi
    Babics, Maxime
    Cruciani, Federico
    Marszalek, Tomasz
    Saleem, Qasim
    Pisula, Wojciech
    Beaujuge, Pierre M.
    CHEMISTRY OF MATERIALS, 2016, 28 (15) : 5415 - 5425
  • [2] Synthesis of 5H-Dithieno[3,2-b:2′,3′-d]pyran as an Electron-Rich Building Block for Donor-Acceptor Type Low-Bandgap Polymers
    Dou, Letian
    Chen, Chun-Chao
    Yoshimura, Ken
    Ohya, Kenichiro
    Chang, Wei-Hsuan
    Gao, Jing
    Liu, Yongsheng
    Richard, Eric
    Yang, Yang
    MACROMOLECULES, 2013, 46 (09) : 3384 - 3390
  • [3] Impact of alkyl side chain on the photostability and optoelectronic properties of indacenodithieno[3,2-b]thiophene-alt-naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole medium bandgap copolymers
    An, Lili
    Tong, Junfeng
    Yang, Chunyan
    Zhao, Xu
    Wang, Xunchang
    Xia, Yangjun
    POLYMER INTERNATIONAL, 2020, 69 (02) : 192 - 205
  • [4] Thieno[3,2-b]pyrrole and Benzo[c][1,2,5]thiadiazole Donor-Acceptor Semiconductors for Organic Field-Effect Transistors
    Gunawardhana, Ruwan
    Bulumulla, Chandima
    Gamage, Prabhath L.
    Timmerman, Adam J.
    Udamulle, Chinthaka M.
    Biewer, Michael C.
    Stefan, Mihaela C.
    ACS OMEGA, 2019, 4 (22): : 19676 - 19682
  • [5] Dithieno[3,2-b:2′,3′-d]pyrrole-benzo[c][1,2,5]thiadiazole conjugate small molecule donors: effect of fluorine content on their photovoltaic properties
    Busireddy, Manohar Reddy
    Chereddy, Narendra Reddy
    Shanigaram, Balaiah
    Kotamarthi, Bhanuprakash
    Biswas, Subhayan
    Sharma, Ganesh Datt
    Vaidya, Jayathirtha Rao
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2017, 19 (31) : 20513 - 20522
  • [6] Synthesis of 5H-Dithieno[3,2-b:2′,3′-d]pyran as an Electron-Rich Building Block for Donor-Acceptor Type Low-Bandgap Polymers (vol 46, pg 3384, 2013)
    Dou, Letian
    Chen, Chun-Chao
    Yoshimura, Ken
    Ohya, Kenichiro
    Chang, Wei-Hsuan
    Gao, Jing
    Liu, Yongsheng
    Richard, Eric
    Yang, Yang
    MACROMOLECULES, 2013, 46 (11) : 4734 - 4734
  • [7] A Ladder-type Heteroheptacene 12H-Dithieno[2',3':4,5]thieno[3,2-b:2',3'-h]fluorene Based D-A Copolymer with Strong Intermolecular Interactions toward Efficient Polymer Solar Cells
    Yang, Mingyan
    Lau, Tsz-Ki
    Xiao, Shengqiang
    Gao, Jianhong
    Wang, Wei
    Lu, Xinhui
    Zhang, Shoujie
    Wu, Jiansheng
    Zhan, Chun
    You, Wei
    ACS APPLIED MATERIALS & INTERFACES, 2017, 9 (40) : 35159 - 35168
  • [8] Dithieno[3,2-b:2′,3′-d]pyrrole-Alkylthiophene-Benzo[c][1,2,5]thiadiazole-Based Highly Stable and Low Band Gap Polymers for Polymer Light-Emitting Diodes
    Mishra, Sarada P.
    Palai, Akshaya K.
    Srivastava, Ritu
    Kamalasanan, Modeeparampil N.
    Patri, Manoranjan
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (23) : 6514 - 6525
  • [9] Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C-H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones
    Xu, Yuanshuang
    Xiao, Yujing
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC LETTERS, 2024, 26 (04) : 786 - 791
  • [10] Cu-catalyzed direct C-H bond functionalization: a regioselective protocol to 5-aryl thiazolo[3,2-b]-1,2,4-triazoles
    Xie, Zengyang
    Zhu, Xiaojun
    Guan, Yangfan
    Zhu, Dunru
    Hu, Hongwen
    Lin, Chen
    Pan, Yi
    Jiang, Juli
    Wang, Leyong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (08) : 1390 - 1398
12