Abstract
The crystals of N-salicylideneaniline (SA) and SA derivatives are classic functional materials that exhibit reversible colour changes (photochromism) and/or excited-state intramolecular proton transfer (ESIPT) fluorescence emission under ultraviolet (UV) light irradiation. In this study, a novel SA derivative was synthesised with an extended alkyl chain, N-(5-bromo-salicylidene)-3-aminoethylpyridine (5Br-SAEP). The photophysical properties of 5Br-SAEP were characterised in the crystalline state. The monohydrated crystal (1H) of 5Br-SAEP was dehydrated to form the anhydrous crystal (1A) at a relative humidity of less than 76%. The photochromic activity was switched by the dehydration phase transition from the non-photochromic 1H to the photochromic 1A. The quantum yield of fluorescence decreased significantly from 8% in 1H to 3% in 1A. The in situ change of photophysical properties occurred due to the change in the crystal structure. This indicated the potential of the solvated crystals of the SAEP derivatives for applications in novel switching or smart materials.
Funding source: Tokyo Institute of Technology
Funding source: Keio Gijuku Academic Development Fund
Acknowledgements
Mr Ishihara of the Instrumental Analysis Center at Yokohama National University is thanked for excellent technical support in recording the solid-state fluorescent spectra. Prof. Hidehiro Uekusa of the Tokyo Institute of Technology is acknowledged for providing great support. Editage (www.editage.com) for English language editing is thanked. This research was supported by Keio Gijuku Academic Development Fund.
Author contributions: The author has accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This study was supported by Keio Gijuku Academic Development Fund.
Conflict of interest statement: The author states no conflict of interest.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2020-0091).
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