Enhanced brightness and electron affinity of terrylenediimide with sulfone-bridged substituents on the bay region

Yan Zhang; Huanying Zhou; Xu Wang; Xinwei Li; Juandi Wei; Yanjun Qiao; Yifang Song; Baoxiang Gao

doi:10.1039/d0cc06956f

Enhanced brightness and electron affinity of terrylenediimide with sulfone-bridged substituents on the bay region

Chem Commun (Camb). 2021 Jan 21;57(5):651-654. doi: 10.1039/d0cc06956f.

Authors

Yan Zhang¹, Huanying Zhou², Xu Wang¹, Xinwei Li¹, Juandi Wei¹, Yanjun Qiao¹, Yifang Song¹, Baoxiang Gao³

Affiliations

¹ Key Laboratory of Analytical Science and Technology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, Hebei, China. bxgao@hbu.edu.cn.
² Tianjin Institute of Environmental and Operational Medicine, Tianjin 300050, P. R. China.
³ Key Laboratory of Analytical Science and Technology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, Hebei, China. bxgao@hbu.edu.cn and Key Laboratory of Medicinal Chemistry and Molecular Diagnosis (Ministry of Education), Hebei University, Baoding 071002, Hebei, China.

PMID: 33346268
DOI: 10.1039/d0cc06956f

Abstract

Terrylenediimide with electron-withdrawing groups (TDI4SF) was synthesized by the attachment of sulfone substituents on the bay region of terrylenediimide. The electron-withdrawing sulfone groups enhance the electron affinity, reduce the LUMO level to -4.37 eV, and endow TDI with excellent anti-oxidation ability. With sulfone substituents, TDI4SF has a red-shifted emission maximum with a peak at 702 nm and high photoluminescence quantum yield.