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Synthesis, crystal structure, photoluminescence, and electroluminescence properties of a new compound containing diphenylmethylene, carbazole, and malononitrile units

Published online by Cambridge University Press:  10 June 2019

Zhaofeng Shi ,
Dayong Zhang ,
Jinnan Huo ,
Hongbo Wang ,
Junsheng Yu ,
Heping Shi  and
Ben Zhong Tang
Zhaofeng Shi*
Affiliation:
School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu 611731, China
Dayong Zhang
Affiliation:
School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu 611731, China
Jinnan Huo
Affiliation:
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
Hongbo Wang
Affiliation:
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
Junsheng Yu*
Affiliation:
School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu 611731, China
Heping Shi*
Affiliation:
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
Ben Zhong Tang*
Affiliation:
Department of Chemistry, Institute for Advanced Study, Division of Biomedical Engineering, Division of Life Science, State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, The Hong Kong University of Science and Technology, Kowloon, Hong Kong 999077, China
*
a)Address all correspondence to these authors. e-mail: jsyu@uestc.edu.cn
b)e-mail: hepingshi@sxu.edu.cn
c)e-mail: tangbenz@ust.hk
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Abstract

In this work, a new phenylethylene derivative, named 2-((3,5-di(9H-carbazol-9-yl)phenyl)(p-tolyl)methylene)malononitrile (DCPTMM), is synthesized and characterized by 1H NMR, 13C NMR spectroscopies, mass spectrum, and X-ray crystallography. Its photophysical properties are systematically studied and the result illustrates that DCPTMM shows aggregation-induced emission (AIE). The X-ray single crystal diffraction shows that the individual structure of crystals is monoclinic system with space group symbol P21/c and presents a twisted propeller-type structure as well as the packing structure of crystals has multiple types of hydrogen bonds (C–H⋯π and C–H⋯N) formed between adjacent molecules, and there is no π–π interaction between the aromatic rings, which is the main reason for the formation of AIE. Nondoped OLED fabricated with DCPTMM as light emitting layer emits greenish yellow light with a maximum emission peak of 554 nm and has relatively good performance with a maximum current efficiency of 5.53 cd/A and a maximum brightness of 6936 cd/m2.

Keywords

chemical synthesiscrystallographic structureoptical properties
Type
Article
Information
Journal of Materials Research , Volume 34 , Issue 17: Focus Issue: Building Advanced Materials via Particle Aggregation and Molecular Self-Assembly , 16 September 2019 , pp. 3000 - 3010
Copyright
Copyright © Materials Research Society 2019 

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