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

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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.

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

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Publication details

The article was received on 16 Aug 2019, accepted on 09 Oct 2019 and first published on 14 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QM00529C
Mater. Chem. Front., 2019, Advance Article

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

    A. Li, N. Chu, J. Liu, H. Liu, J. Wang, S. Xu, H. Cui, H. Zhang, W. Xu and Z. Ma, Mater. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QM00529C

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