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Solid-state photochromic materials have attracted much more attention due to their actual potential applications in photoactive devices. Here, three new compounds (1-phenyl-3-methyl-4-(3-fluoro/chloro/bromobenzal)-5-hydroxypyrazole 4-phenylthiosemicarbazones) were synthesized, which exhibited reversible solid state photochromic properties upon UV/Vis light irradiation. Their photochromic properties, first-order kinetics and fatigue resistance were investigated by time-dependent UV-Vis absorption spectroscopy. The results showed that their fatigue resistance and addressability were enhanced with the increase in the electron-withdrawing ability of the substituents on the phenyl group at the 4-position of the pyrazolone ring. Thus, 1-phenyl-3-methyl-4-(3-fluorobenzal)-5-hydroxypyrazole 4-phenylthiosemicarbazone exhibited good photochromic properties and high fatigue resistance. Based on single crystal X-ray diffraction and FT-IR analyses, the photochromic mechanism involved intra/intermolecular proton transfer. [ABSTRACT FROM AUTHOR]

Three carbothioamide derivatives with reversible P-type photochromic properties in the solid state were synthesized in a one-step reaction. Based on the single crystal structures, the FT-IR spectra and theory calculations, the proposed photochromic mechanism was the intermolecular proton transfer between the thio-keto and thio-enol tautomer. Nanofibrous membranes were prepared by electrospinning, which showed improved reversible photochromic properties in comparison of the compound itself. This work may open a new pathway for design and synthesis of the new solid-state photochromic materials with high-performance. [ABSTRACT FROM AUTHOR]