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Updated: Sep 15, 2025

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Published on: June 10, 2021
High-contrast mechanofluorochromism of two AIE-active D-A-π-D' deep red-emitting triphenylamine-based dicyanodiaryl
Hanrong Liu1, Baobei Liu1, Huizhuan Zhu1
1Key Laboratory of Magnetic Molecules and Magnetic Information Material of Ministry of Education, School of Chemistry and Chemical Engineering, Shanxi Normal University, Taiyuan 030032, PR China.
Abstract:
In this study, we successfully constructed two AIE-active D-A-π-D' red-emitting triphenylamine-based dicyanodiaryl derivatives, namely (E)-2-(1-(4-(diphenylamino)phenyl)-3-(4-hydroxyphenyl)allylidene)malononitrile (p-DPHAM) and (E)-2-(1-(4-(diphenylamino)phenyl)-3-(3-hydroxyphenyl)allylidene)malononitrile (m-DPHAM). A comprehensive photophysical characterization combined with theoretical calculations elucidated their non-planar, twisted molecular conformations, donor-acceptor frameworks, and notable solvatochromic properties. Both compounds demonstrated pronounced AIE behavior in THF-water mixtures. These two derivatives displayed remarkable mechanofluorochromic behavior with a red-shift for p-DPHAM (52 nm) and m-DPHAM (41 nm), respectively. Powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC) and field-emission scanning electron microscopy (FESEM) analyses indicated that the reversible mechanofluorochromism originates from crystalline-to-amorphous phase transitions. Single-crystal structural analysis revealed that external mechanical force disrupted specific intramolecular interactions, leading to a transformation in stacking pattern. It is anticipated that this work offers valuable perspectives for the design of high-contrast mechano-responsive luminescent materials.
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