Ladder-type Heteroarenes: Up to 15 Rings with Five Imide Groups

Yingfeng Wang; Han Guo; Shaohua Ling; Iratxe Arrechea-Marcos; Yuxi Wang; Juan Teodomiro López Navarrete; Rocio Ponce Ortiz; Xugang Guo

doi:10.1002/anie.201702225

Ladder-type Heteroarenes: Up to 15 Rings with Five Imide Groups

Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9924-9929. doi: 10.1002/anie.201702225. Epub 2017 Jun 28.

Authors

Yingfeng Wang¹, Han Guo¹, Shaohua Ling¹, Iratxe Arrechea-Marcos², Yuxi Wang^{1

3}, Juan Teodomiro López Navarrete², Rocio Ponce Ortiz², Xugang Guo¹

Affiliations

¹ Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, South University of Science and Technology of China, No. 1088, Xueyuan Road, Shenzhen, Guangdong, 518055, China.
² Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, 29071, Málaga, Spain.
³ Department of Chemistry, Wuhan University, Wuhan, Hubei, 430072, China.

PMID: 28657167
DOI: 10.1002/anie.201702225

Abstract

A series of novel imide-functionalized ladder-type heteroarenes with well-defined structure and controllable conjugation lengths were synthesized and characterized. The synthetic route shows remarkable efficacy for constructing the electron-deficient ladder backbones. π-Conjugation extension leads to narrowed band gaps with enhanced electron affinities. The ladder arenes are incorporated into organic thin-film transistors, and show encouraging electron mobilities of 0.013-0.045 cm² V^-1 s^-1 . The heteroarenes reported here provide a remarkable platform for fundamental physicochemical studies and materials innovation in organic electronics.

Keywords: conjugation; heteroarenes; ladder polymers; semiconductors; structure-activity relationships.

Publication types

Research Support, Non-U.S. Gov't