Synthesis, Structure and Properties of a Novel Photochromic Dyad Based on Spirooxazine and Ferrocene

Abstract

Abstract:

A novel photochromic compound 2 based on spirooxazine and ferrocene residue was synthesized by esterification reaction of 9′-hydroxy spirooxazine and ferrocene carboxylic acid in the presence of DCC. Its structure was characterized by ¹H NMR, ¹³C NMR, IR, HRMS, and X-ray single crystal diffraction. The UV measurement show that compound 2 has good photochromic properties in several organic solvents and good fatigue resistance property. The special property in dichloromethane was proved to be caused by acidichromism when irradiated with high pressure Hg lamp without ice bath. The photochromic property of compound 2 in solid PMMA thin film was also studied. In the acidic condition, or under irradiation with high pressure Hg lamp without ice bath, the dichloromethane solution of compound 2 exhibit a good fluorescence. Additionally, compound 2 show a good reversibility of the redox, which is determined by CV. Ferrocene derivatives have the property of absorbing light, and this property may be helpful to extend the fatigue life of photochromic compounds. Besides, the new compound may posses photo-electromagnetic property owing to the existence of metal ion.

Key words: Spirooxazine, Photochromism, Fluorescence, Cyclic voltammetry, Ferrocene

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YANG Su-Hua, PANG Mei-Li*, GUO Xin-Fu, HUO Xiao-Lian, HAN Jie, MENG Ji-Ben*. Synthesis, Structure and Properties of a Novel Photochromic Dyad Based on Spirooxazine and Ferrocene[J]. Chem. J. Chinese Universities, 2009, 30(6): 1135.

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Synthesis, Structure and Properties of a Novel Photochromic Dyad Based on Spirooxazine and Ferrocene

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