Pressure-induced remarkable luminescence switch of a dimer form of donor–acceptor–donor triphenylamine (TPA) derivative

Aisen Li; Ning Chu; Jianwei Liu; Hao Liu; Jing Wang; Shuping Xu; Haining Cui; Hongyu Zhang; Weiqing Xu; Zhiyong Ma

doi:10.1039/C9QM00529C

Pressure-induced remarkable luminescence switch of a dimer form of donor–acceptor–donor triphenylamine (TPA) derivative†

Aisen Li,‡^ab Ning Chu,‡^a Jianwei Liu,^c Hao Liu,^d Jing Wang,^a Shuping Xu,

^a Haining Cui,^b Hongyu Zhang,

^d Weiqing Xu

*^a and Zhiyong Ma

*^c

Author affiliations

* Corresponding authors

^a State Key Laboratory of Supramolecular Structure and Materials, Institute of Theoretical Chemistry, Jilin University, Changchun, P. R. China
E-mail: xuwq@jlu.edu.cn

^b College of Physics, Jilin University, Changchun 130012, P. R. China

^c Beijing State Key Laboratory of Organic-Inorganic Composites, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China
E-mail: mazhy@mail.buct.edu.cn

^d State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, P. R. China

Abstract

Two newly synthesized molecules with a twisted donor–acceptor–donor (D–A–D) structure were achieved, noted as TPA-Ph-CN and TPA-Py-CN, and their solvatochromic effects and mechanochromic properties upon grinding and/or under hydrostatic pressure were investigated deeply. The comparison of their solvatochromic behaviors demonstrates that TPA-Py-CN shows a stronger intramolecular charge transfer (ICT) effect than TPA-Ph-CN due to the substitution of electron-deficient acceptor from Ph-CN to Py-CN. Photophysical characterizations together with the analysis of crystal structures indicate that TPA-Py-CN exhibits a distinct dimer structure with C–H⋯π interactions, but TPA-Ph-CN does not. As a result, TPA-Py-CN shows green emission with three bands and the peak at 538 nm is assigned to excimer, while TPA-Ph-CN presents blue emission with only one band. Upon grinding, TPA-Py-CN shows more sensitive responsiveness to pressure than TPA-Ph-CN and exhibits a size-dependent emission property. TPA-Ph-CN only displays continuous red-shifted and broadened emission under hydrostatic pressure. In contrast, high pressure experiments and theoretical calculations of TPA-Py-CN demonstrate that the excimer fluorescence wavelength is pressure-independent. This study is helpful for better understanding intrinsic essences of the molecular structure and the properties of mechano-responsive organic molecules.

Materials Chemistry Frontiers

Pressure-induced remarkable luminescence switch of a dimer form of donor–acceptor–donor triphenylamine (TPA) derivative†

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Pressure-induced remarkable luminescence switch of a dimer form of donor–acceptor–donor triphenylamine (TPA) derivative

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