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Pyrene‐fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies
Author(s) -
Wang Qingsong,
Gao Wei,
Chen Yan,
Wang Xiaohui,
Zeng Jin,
Liu Yiwei,
Ran Huijuan,
Hu Zhen,
Bai Jie,
Feng Xing,
Redshaw Carl,
Chen Qing,
Hu JianYong
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000616
Subject(s) - chemistry , pyrene , quantum yield , quenching (fluorescence) , stacking , photochemistry , fluorescence , yield (engineering) , solubility , crystal (programming language) , photoluminescence , crystallography , organic chemistry , optoelectronics , materials science , optics , physics , computer science , metallurgy , programming language
Molecular packing and microstructure can play a crucial role in the photophysical and electronic properties of organic semiconductor materials. This article presents six pyrene‐fused dibenzoazatetracenes 3 and the relationship between their molecular structures and the emission, and as well as the morphology has been investigated. All of the compounds display an aggregation‐caused emission quenching effect due to the extended π‐conjugation associated with the close π‐π stacking in their crystal structures. In terms of fluorescence, the compounds emitted sky‐blue emission with a maximum peak (λ maxem ) in the range 469–474 nm with a quantum yield (Φ f ) of 0.37–0.50 in solution. In the solid state, the emission maximum red‐shifts to ∼528 nm and possesses a relatively low quantum yield (<0.16). In addition, the electronic effects of the terminal group shows only a limited effect on the emission behavior. On the other hand, tert ‐butyl groups have been introduced at the pyrene core, and contribute to enhance the solubility of the compound, and also improve the quality of the morphology.