Cyano-Functionalized Diarylethene Derivatives with Aggregation-Induced Emission Enhancement and Piezofluorochromic Behaviours
Ying Liu A B , Yuqi Cao A B , Xue Li A B , Yang Li A B C D and Bowei Wang A B C DA School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China.
B Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300350, China.
C Tianjin Engineering Research Center of Functional Fine Chemicals, Tianjin 300350, China.
D Corresponding authors. Email: liyang777@tju.edu.cn; bwwang@tju.edu.cn
Australian Journal of Chemistry 72(5) 369-374 https://doi.org/10.1071/CH18450
Submitted: 8 September 2018 Accepted: 13 January 2019 Published: 19 February 2019
Abstract
Four donor–acceptor (D-A) type phenothiazine derivatives were designed and synthesized and all of them exhibited an aggregation-induced emission enhancement (AIEE) effect and red-shifted piezofluorochromic (PFC) behaviour. Moreover, it was found that the compound containing a shorter alkyl chain displayed more remarkable PFC properties. This result was probably ascribed to highly twisted conformations which can lead to loose solid molecular packing with cavities and weak interactions. After they were pressed, the planarization of the molecular conformation increased and molecular conjugation degree enhanced, resulting in a red-shift in the photoluminescence spectrum. In addition, optimized geometric structures indicate that the compound with a longer alkyl chain has a more planer geometric structure, which leads to a smaller bathochromic shift upon grinding. In summary, we provide a new path to regulate the PFC behaviours of fluorescent materials by changing the length of their substituted alkyl chain.
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