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Synthesis and photovoltaic properties of novel polymers base
on thiophene derivatives with electron-deficient
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3-nitro-1,2,4-triazole side chains for polymer solar cells#
Li Xinwei1, Zhao Bin2, Tang Peng1, Cao Zhencai1, Kang Huaiyin1, Huang Hongyan1,
Shen Ping1, Tan Songting2**
(1. College of Chemistry and Key Laboratory of Environmentally Friendly Chemistry and
Applications of Ministry of Education, Xiangtan University, HuNan XiangTan 411105;
2. Key Laboratory of Advanced Functional Polymeric Materials of College of Hunan Province,
Xiangtan University, HuNan XiangTan 411105)
Abstract: Three novel soluble alternating conjugated copolymers PT-TZN, PF-TZN, and PBDT-TZN,
comprised of thiophene, fluorene, benzo[1,2-b:4,5-b’]dithiophene and thiophene derivatives with
3-nitro-1,2,4-triazole side chains, were synthesized via the palladium-catalyzed Suzuki coupling
reaction and Stille coupling reaction. The effects of 3-nitro-1,2,4-triazole on the thermal, photophysical,
electrochemical and photovoltaic properties were investigated. The introduction of the 3-nitro-1,2,4-
triazole side chains benefits to lowering the bandgaps of the polymers. The bulk-heterojunction
polymer solar cells were fabricated based on the blend of the as-synthesized polymers and the fullerene
acceptor [6, 6]-phenyl-C61-butyric acid methyl ester (PCBM). The maximum power conversion
efficiency (PCE = 1.13%) was obtained with PBDT-TZN as the electron donor under the illumination
of AM 1.5, 100 mW cm-2. The study results indicate that low bandgap derived from too strong
electron-withdrawing groups does not always benefit to the PCEs of PSCs.
Keywords: polymer chemistry and physics; conjugated polymers; thiophene derivatives;
3-nitro-1,2,4-triazole; fluorine; benzo[1,2-b: 4, 5-b’]dithiophene
0 Introduction
In the past decade, polymer solar cells (PSCs) have gained serious attention in both academia
and industry. As a simple and efficient way to convert solar energy to electri
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