Thieno[3,2-b]thiophene b ]thiophene flanked para-azaquinodimethane it-extended aromatic-quinoidal polymers

被引:0
作者
Dyaga, Bharath [1 ]
Waliszewski, Witold [2 ]
Ling, Zhitian [3 ]
Mayarambakam, Sasikumar [1 ]
Boyron, Olivier [4 ]
Pisula, Wojciech [2 ,3 ]
Schmaltz, Bruno [1 ]
机构
[1] Univ Tours, EA6299, Lab Phys Chim Mat & Electrolytes Energie (PCM2E), F-37200 Tours, France
[2] Lodz Univ Technol, Fac Chem, Dept Mol Phys, Zeromskiego 116, PL-90924 Lodz, Poland
[3] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany
[4] Univ Lyon, Univ Lyon 1, Equipe PCM, CPE Lyon,CNRS UMR 5128,Lab CP2M, F-69100 Villeurbanne, France
关键词
Extended pi-conjugation; Para-azaquinodimethane; OFET; Bond length alternation; FIELD-EFFECT TRANSISTORS; ALKYL SIDE-CHAINS; CONJUGATED POLYMERS; BUILDING-BLOCK; SOLAR-CELLS; DIKETOPYRROLOPYRROLE POLYMER; RATIONAL DESIGN; BAND; ACCEPTOR; SEMICONDUCTORS;
D O I
10.1016/j.synthmet.2024.117751
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
A series of thieno[3,2-b]thiophene (TT) flanked para-azaquinodimethane (p-AQM) based quinoidal conjugated polymers PAQM2TT-T, PAQM2TT-BT and PAQM3TT were designed in a strategy to extend the aromatic-quinoidal pi-system. The three polymers were synthesized by Stille polycondensation, and their opto-electronic properties and device performance in field-effect transistors have been explored. From absorption spectroscopy, the polymers show low bandgaps (1.54-1.57 eV) and high HOMO energy levels. They exhibit typical p-type behavior according to the results of the characterization of the field-effect transistors with average charge carrier mobilities of 0.08 cm(2) V-1 s(-1) for PAQM2TT-T, 0.12 cm(2) V-1 s(-1) for PAQM2TT-BT and 0.05 cm(2) V-1 s(-1) for PAM3TT. This report presents an alternative pi-extended quinoidal-donor strategy to control the molecular design and properties of new p-AQM-based conjugated polymers.
引用
收藏
页数:8
相关论文
共 50 条
[41]   One-pot synthesis and thermal stability of thiophene-bridged thieno[3,2-b] thiophene donor-based copolymers [J].
Desalegn, Behayilu S. ;
Bekri, Nika ;
Hone, Fekadu G. ;
Andoshe, Dinsefa M. ;
Mammo, Wendimagegn ;
Abdissa, Zelalem ;
Bosman, Gurthwin ;
Tegegne, Newayemedhin A. .
MATERIALS TODAY COMMUNICATIONS, 2021, 29 (29)
[42]   Thieno[3,2-b]thiophene derivatives exhibiting semiconducting liquid-crystalline phases at lower temperatures [J].
Kim, Yuna ;
Funahashi, Masahiro ;
Tamaoki, Nobuyuki .
RSC ADVANCES, 2014, 4 (105) :60511-60518
[43]   New star-shaped molecules derived from thieno[3,2-b]thiophene unit and triphenylamine [J].
Metri, N. ;
Sallenave, X. ;
Beouch, L. ;
Plesse, C. ;
Goubard, F. ;
Chevrot, C. .
TETRAHEDRON LETTERS, 2010, 51 (50) :6673-6676
[44]   A Redox-Dependent Electrochromic Material: Tetri-EDOT Substituted Thieno[3,2-b]thiophene [J].
Shi, Jingjing ;
Zhu, Xiaosi ;
Xu, Panpan ;
Zhu, Mengmeng ;
Guo, Yitong ;
He, Yaowu ;
Hu, Zhao ;
Murtaza, Imran ;
Yu, Hongtao ;
Yan, Lijia ;
Goto, Osamu ;
Meng, Hong .
MACROMOLECULAR RAPID COMMUNICATIONS, 2016, 37 (16) :1344-1351
[45]   Solution-Processable Low Voltage Organic Transistors of Thieno[3,2-b]thiophene-Based Conducting Polymer [J].
Kim, Joo Yeon ;
Lee, Ja-Eun ;
Kim, Tae-Dong ;
Baek, Nam Seob .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2014, 600 (01) :107-115
[46]   Exploring the electrochromic properties of poly(thieno[3,2-b]thiophene)s decorated with electron-deficient side groups [J].
Shao, Shan ;
Shi, Jingjing ;
Murtaza, Imran ;
Xu, Panpan ;
He, Yaowu ;
Ghosh, Sanjay ;
Zhu, Xiaosi ;
Perepichka, Igor F. ;
Meng, Hong .
POLYMER CHEMISTRY, 2017, 8 (04) :769-784
[47]   Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units [J].
McEntee, Greg J. ;
Skabara, Peter J. ;
Vilela, Filipe ;
Tierney, Steven ;
Samuel, Ifor D. W. ;
Gambino, Salvatore ;
Coles, Simon J. ;
Hursthouse, Michael B. ;
Harrington, Ross W. ;
Clegg, William .
CHEMISTRY OF MATERIALS, 2010, 22 (09) :3000-3008
[48]   The effect of thieno[3,2-b]thiophene on the absorption, charge mobility and photovoltaic performance of diketopyrrolopyrrole-based low bandgap conjugated polymers [J].
Li, Yongxi ;
Chang, Chih-Yu ;
Chen, Yu ;
Song, Yi ;
Li, Chang-Zhi ;
Yip, Hin-Lap ;
Jen, Alex K. -Y. ;
Li, Chao .
JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (45) :7526-7533
[49]   Largely π-Extended Thienoacenes with Internal Thieno[3,2-b]thiophene Substructures: Synthesis, Characterization, and Organic Field-Effect Transistor Applications [J].
Yamamoto, Tatsuya ;
Nishimura, Takeshi ;
Mori, Takamichi ;
Miyazaki, Eigo ;
Osaka, Itaru ;
Takimiya, Kazuo .
ORGANIC LETTERS, 2012, 14 (18) :4914-4917
[50]   Benzotriazole-Based p-Type Polymers with Thieno[3,2-b]thiophene π-Bridges and Fluorine Substituents To Realize High VOC [J].
Chen, You ;
Zhang, Qianqian ;
Du, Mengzhen ;
Li, Gongqiang ;
Li, Zijie ;
Huang, Hui ;
Geng, Yanfang ;
Zhang, Xiaoli ;
Zhou, Erjun .
ACS APPLIED POLYMER MATERIALS, 2019, 1 (04) :906-913