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Thermo‐ and Acid‐Responsive Photochromic Spironaphthoxazine‐Containing Organogelators
Authors:Yongguang Li  Keith Man‐Chung Wong Dr.  Anthony Yiu‐Yan Tam Dr.  Lixin Wu Prof. Dr.  Vivian Wing‐Wah Yam Prof. Dr.
Affiliation:1. State Key Laboratory of Supramolecular Structure and Materials and College of Chemistry, Jilin University, Changchun 130012 (P.R. China);2. Institute of Molecular Functional Materials and Department of Chemistry, The University of Hong Kong, Pokfulam Road (Hong Kong)
Abstract:A series of photochromic spironaphthoxazine derivatives has been designed, synthesized, and characterized by using 1H NMR spectroscopy, FAB mass spectrometry, and elemental analysis. Their photophysical and photochromic behavior have been investigated. Two of the compounds (G12‐en‐SA‐SO and G16‐en‐SA‐SO) have been shown to be capable of forming stable thermoreversible organogels in organic solvents, tested by the “stable‐to‐inversion of a test tube” method. Addition of p‐toluenesulfonic acid was found to induce the formation of stable organogels at concentrations below that of the critical gelation concentration (c.g.c.), with a concomitant change in color from colorless to purple. Transmission electron microscopy and scanning electron microscopy of the xerogels showed typical fibrous structures in the micrometer scale. The activation parameters for the bleaching reaction of G8‐en‐SA‐SO in the solution state and G16‐en‐SA‐SO in the gel state have been determined in ethanol through kinetic studies at various temperatures. The results showed that the rate of the bleaching reaction in the gel state was much slower than that in the solution state.
Keywords:acidichromism  organogels  photochromism  spironaphthoxazine  supramolecular chemistry
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