4Department of Design & Manufacturing Engineering, Jeonbuk National University, Jeonju 54896, South Korea3School of Pharmacy, Jining Medical University, Rizhao, Shandong 276826, China1School of Pharmacy, Shandong First Medical University & Shandong Academy of Medical Sciences, Tai'an, Shandong 271016, China2Z.Q. and M.Z. contributed equally to this work.
刊名
Journal of Photochemistry and Photobiology A: Chemistry
As a prominent class of photochromic systems, diarylethenes offer an ideal platform for investigating media-dependent photochromic properties through rational molecular design. In this work, we systematically explored the synergistic effects of the ethene bridge moiety and side-chain aromatic substituents on modulating molecular conformations and photochromic performance. Three diarylethene derivatives , featuring a methyl-1H-indole ethene bridge and benzothiophene or phenyl-substituted thiophen...更多
As a prominent class of photochromic systems, diarylethenes offer an ideal platform for investigating media-dependent photochromic properties through rational molecular design. In this work, we systematically explored the synergistic effects of the ethene bridge moiety and side-chain aromatic substituents on modulating molecular conformations and photochromic performance. Three diarylethene derivatives , featuring a methyl-1H-indole ethene bridge and benzothiophene or phenyl-substituted thiophene/thiazole side chains, were synthesized via Suzuki-Miyaura cross-coupling reactions. Structural and conformational analyses reveal that steric hindrance between the indole bridge and the side chains dictates the coexistence of parallel and antiparallel conformers in 1o, whereas 2o and 3o exclusively adopt a single stable conformation. This variation in steric hindrance further modulates the reactive carbon‑carbon distance , thereby tuning their photochemical reactivity. Notably, 3o possesses an additional C₂-symmetric molecular structure confirmed by NMR, arising from intramolecular heteroatomic interactions that shorten the reactive carbon distance. All three compounds exhibit reversible photochromic behaviors in solution, PMMA films, and the solid state, with media-dependent characteristics under specific light irradiation. These results establish correlations among steric hindrance, molar conformation, reactive carbon distance, and photochromic performance, further validating the promising potential of such indole-bridged diarylethene systems for advanced applications including molecular photoswitches, optical data storage, and multi-medium color-switching devices.收起
