5,5′‐Diazaisoindigo: an Electron‐Deficient Building Block for Donor–Acceptor Conjugated Polymers

• Published in: Chemistry, an Asian journal an Asian journal, 2017-02, Vol.12 (3), p.302-307
• Main Authors: Lu, Yang, Liu, Yi, Dai, Ya‐Zhong, Yang, Chi‐Yuan, Un, Hio‐Ieng, Liu, Si‐Wei, Shi, Ke, Wang, Jie‐Yu, Pei, Jian
• Format: Article
• Language: English
• Subjects: Chemistry; conjugated polymers; diazaisoindigo; donor–acceptor systems; electron-deficient compounds
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201601671

A novel electron‐deficient building block, 5,5′‐diazaisoindigo (5DNIID), was synthesized through a facile method in good yield. As a derivative of isoindigo, 5DNIID shows an ultra‐low LUMO level of −3.92 eV after incorporation of two electron‐deficient nitrogen atoms into the para‐position of the amine groups in the isoindigo π skeleton. Modified polymerization conditions were applied to efficiently afford the donor–acceptor (D–A) conjugated polymer 5DNIID‐2T, which exhibited a p‐type charge transport property. A novel electron‐deficient building block, 5,5′‐diazaisoindigo (5DNIID), was synthesized through a facile method, which showed an ultra‐low LUMO level of −3.92 eV owing to the introduction of two electron‐deficient nitrogen atoms into the para‐position of the amine groups in the isoindigo π skeleton. A donor–acceptor conjugated polymer 5DNIID‐2T, which exhibited typical p‐type charge transport behavior, was constructed.