Direct access to 4,8-functionalized benzo[1,2-b:4,5-b′]dithiophenes with deep low-lying HOMO levels and high mobilities

Enwei Zhu; Guidong Ge; Jingkun Shu; Mingdong Yi; Linyi Bian; Jiefeng Hai; Jiangsheng Yu; Yun Liu; Jie Zhou; Weihua Tang

doi:10.1039/C4TA01226G

Direct access to 4,8-functionalized benzo[1,2-b:4,5-b′]dithiophenes with deep low-lying HOMO levels and high mobilities†

Enwei Zhu,^a Guidong Ge,^a Jingkun Shu,^b Mingdong Yi,^b Linyi Bian,^a Jiefeng Hai,^a Jiangsheng Yu,^a Yun Liu,^a Jie Zhou^a and Weihua Tang*^a

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* Corresponding authors

^a Key Laboratory of Soft Chemistry and Functional Materials, Nanjing University of Science and Technology, Nanjing 210094, China
E-mail: whtang@njust.edu.cn
Fax: +86 25 8431 7311
Tel: +86 25 8431 7311

^b Key Laboratory of Organic Electronics and Information Displays, Institute of Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing 210046, China
E-mail: iammdyi@njupt.edu.cn

Abstract

A general methodology has been proposed for the straightforward access to 4,8-functionalized benzo[1,2-b:4,5-b′]dithiophenes (BDTs) via Pd mediated coupling reactions including Suzuki–Sonogashira coupling and carbon–sulfur bond formation reactions. This versatile platform can be used to construct a library of BDT core centred conjugated systems, featuring large fused-ring structure and good charge mobility, where a hole mobility of 0.061 cm² V⁻¹ s⁻¹ is demonstrated. With the energy level fine-tuned with functionalization, the charge transporting BDTs show great potential for donor–acceptor polymers.

Journal of Materials Chemistry A

Direct access to 4,8-functionalized benzo[1,2-b:4,5-b′]dithiophenes with deep low-lying HOMO levels and high mobilities†

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Direct access to 4,8-functionalized benzo[1,2-b:4,5-b′]dithiophenes with deep low-lying HOMO levels and high mobilities

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