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Synthesis and photovoltaic properties of conjugated copolymers bearing planar acenaphtho[1,2-b]quinoxaline moiety with deep HOMO level

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Abstract

A series of alternating copolymers (PC-AQx, PT-DTAQx, PC-DTAQx, PF-DTAQx, and PBDT-DTAQx) bearing novel planar acenaphtho[1,2-b]quinoxaline (AQx) or 8,11-di(thiophen- 2-yl)acenaphtho[1,2-b]quinoxaline (DTAQx)-acceptor cores have been synthesized via Suzuki or Stille coupling reactions. UV–vis absorption and GIXRD characterization results indicated that the presence of planar DTAQx unit is favorable for the promotion of well-ordered interchain packing in the solid state, and the incorporation of planar electron-donating benzo[1,2-b: 4,5-b′]-dithiophene (BDT) moiety would be propitious to the molecular self-organization. Electrochemical measurement results suggested that four copolymers possess deep HOMO energy level of −5.5 ~ −5.6 eV. The polymer solar cell with structure of ITO/PEDOT:PSS(30 nm)/polymer:PCBM (60 nm)/Bphen(10 nm)/Ag(100 nm) exhibited the highest V oc of 0.84 V with PF-DTAQx as p-type polymer, while the best power conversion efficiency (PCE) of 0.9 % was obtained using a blend of PBDT-DTAQx and PCBM (1:4) as active layer.

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Acknowledgements

This work was supported by the National Nature Science Foundation of China (Project grant No. 50803040, 20872103, 61177032, and 21072139) and the Open Project Program of Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, China (No. 10HJYH02). We are grateful to the Analytical & Testing Center of Sichuan University for providing NMR, GIXRD and UV–vis characterization for the intermediates and objective polymers.

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Authors and Affiliations

  1. College of Chemistry, Sichuan University, Chengdu, 610064, Pepole’s Republic of China

    Yong Zou, Zhanyuan Zhang, Yan Huang, Zhiyun Lu, Qing Jiang & Xuemei Pu

  2. State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China, Chengdu, 610054, Pepole’s Republic of China

    Zhiqiang Guan, Nana Wang & Junsheng Yu

  3. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Hunan, 411105, Pepole’s Republic of China

    Yu Liu

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  1. Yong Zou
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  2. Zhiqiang Guan
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  4. Yan Huang
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Correspondence to Yan Huang, Zhiyun Lu or Junsheng Yu.

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Zou, Y., Guan, Z., Zhang, Z. et al. Synthesis and photovoltaic properties of conjugated copolymers bearing planar acenaphtho[1,2-b]quinoxaline moiety with deep HOMO level. J Mater Sci 47, 5535–5545 (2012). https://doi.org/10.1007/s10853-012-6446-7

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