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A Twisted Thieno[3,4-b]thiophene-Based Electron Acceptor Featuring a 14-π-Electron Indenoindene Core for High-Performance Organic Photovoltaics

A Twisted Thieno[3,4-b]thiophene-Based Electron Acceptor Featuring a 14-π-Electron Indenoindene Core for High-Performance Organic Photovoltaics

Sheng Jie Xu, Zichun Zhou, Wuyue Liu, Zhongbo Zhang, Feng Liu, Hongping Yan, Xiaozhang Zhu

Adv Mater. 2017 Nov;29(43).

PMID: 28985002

Abstract:

With an indenoindene core, a new thieno[3,4-b]thiophene-based small-molecule electron acceptor, 2,2'-((2Z,2'Z)-((6,6'-(5,5,10,10-tetrakis(2-ethylhexyl)-5,10-dihydroindeno[2,1-a]indene-2,7-diyl)bis(2-octylthieno[3,4-b]thiophene-6,4-diyl))bis(methanylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (NITI), is successfully designed and synthesized. Compared with 12-π-electron fluorene, a carbon-bridged biphenylene with an axial symmetry, indenoindene, a carbon-bridged E-stilbene with a centrosymmetry, shows elongated π-conjugation with 14 π-electrons and one more sp3 carbon bridge, which may increase the tunability of electronic structure and film morphology. Despite its twisted molecular framework, NITI shows a low optical bandgap of 1.49 eV in thin film and a high molar extinction coefficient of 1.90 × 105 m-1 cm-1 in solution. By matching NITI with a large-bandgap polymer donor, an extraordinary power conversion efficiency of 12.74% is achieved, which is among the best performance so far reported for fullerene-free organic photovoltaics and is inspiring for the design of new electron acceptors.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP121134381	3-(2-Ethylhexyl)thiophene		121134-38-1	Price

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