Isomers of Pyrene-Imidazole Compounds: Synthesis and Configuration Effect on Optical Properties

Yulong Liu; Tong Shan; Liang Yao; Qing Bai; Yachen Guo; Jinyu Li; Xiao Han; Weijun Li; Zhiming Wang; Bing Yang; Ping Lu; Yuguang Ma

doi:10.1021/acs.orglett.5b02879

Isomers of Pyrene-Imidazole Compounds: Synthesis and Configuration Effect on Optical Properties

Org Lett. 2015 Dec 18;17(24):6138-41. doi: 10.1021/acs.orglett.5b02879. Epub 2015 Dec 7.

Authors

Yulong Liu¹, Tong Shan¹, Liang Yao¹, Qing Bai¹, Yachen Guo¹, Jinyu Li¹, Xiao Han¹, Weijun Li¹, Zhiming Wang², Bing Yang¹, Ping Lu¹, Yuguang Ma³

Affiliations

¹ State Key Laboratory of Supramolecular Structure and Materials, Jilin University , 2699 Qianjin Avenue, Changchun 130012, China.
² School of Petrochemical Engineering, Shenyang University of Technology , Liaoyang 111003, China.
³ Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology , Guangzhou 510640, China.

PMID: 26642245
DOI: 10.1021/acs.orglett.5b02879

Abstract

Two pyrene-imidazole-based structural isomers, axisymmetric syn-PyDTI and centrosymmetric anti-PyDTI, have been easily produced and successfully separated in a one-pot reaction. Crystalline syn-PyDTI exhibited a 2-fold higher quantum efficiency than anti-PyDTI and displayed a much better performance in OLEDs with a ηc.max of 11.4 cd A(-1) (8.8 cd A(-1) for anti-PyDTI), although they possess the same apparent electronic structure. Observations revealed that the molecular excited-state properties are derived from distinct structural symmetries.

Publication types

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