A new unsymmetrical bisspiropyran was synthesized on the basis of 2,4-dihydroxyisophthalic aldehyde with naphthoxazinone and indoline fragments in the structure. The structure of the obtained compound was proved by the data from 1H NMR and IR spectroscopy and X-ray crystallographic analysis. The photochromic characteristics of the obtained compound were investigated. It was established by means of the data from B3LYP/6-31G** quantum-chemical calculations that irradiation of a solution of the obtained biphotochrome with unfiltered light leads to opening of both pyran fragments. This is the first corroborated example of the twofold cleavage of Cspiro–O bonds for compounds of this class.
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Dedicated to Professor M. A. Yurovskaya on her birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 357-372, March, 2010.
For Communication 32 see [1].
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Mukhanov, E.L., Alekseenko, Y.S., Dorogan, I.V. et al. Photochromic and thermochromic spiranes 33. Synthesis of a new indolinonaphthoxazino- bisspiropyran and investigation of its photochromic characteristics. Chem Heterocycl Comp 46, 279–290 (2010). https://doi.org/10.1007/s10593-010-0503-4
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DOI: https://doi.org/10.1007/s10593-010-0503-4