Photophysical property change of N-(5-bromo-salicylidene)-3-aminoethylpyridine monohydrated crystals via dehydration phase transition

Abstract

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.