5,5'-Diazaisoindigo: an Electron-Deficient Building Block for Donor-Acceptor Conjugated Polymers

Yang Lu; Yi Liu; Ya-Zhong Dai; Chi-Yuan Yang; Hio-Ieng Un; Si-Wei Liu; Ke Shi; Jie-Yu Wang; Jian Pei

doi:10.1002/asia.201601671

5,5'-Diazaisoindigo: an Electron-Deficient Building Block for Donor-Acceptor Conjugated Polymers

Chem Asian J. 2017 Feb 1;12(3):302-307. doi: 10.1002/asia.201601671. Epub 2017 Jan 9.

Authors

Yang Lu¹, Yi Liu², Ya-Zhong Dai¹, Chi-Yuan Yang¹, Hio-Ieng Un¹, Si-Wei Liu¹, Ke Shi¹, Jie-Yu Wang¹, Jian Pei¹

Affiliations

¹ Beijing National Laboratory for Molcular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center for Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
² College of Life Science, Shandong Normal University, Jinan, Shandong, 250014, China.

PMID: 28067029
DOI: 10.1002/asia.201601671

Abstract

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.

Keywords: conjugated polymers; diazaisoindigo; donor-acceptor systems; electron-deficient compounds.