Conclusions
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1.
An x-ray crystallographic and photochemical investigation of the photochromic 1′-phenyl-3′,3′-dimethyl-6-nitrospiro(indoline-2,2′-[2H-]benzothiopyran) was undertaken.
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2.
The Cspiro-S bond which is cleaved in the spirothiopyrans during photoexcitation, like the Cspiro-O bond in spiropyrans, is elongated and is the weakest in the molecule.
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3.
In contrast to the Cspiro-O bond of the spiropyrans, the elongation of the Cspiro-S bond in the spirothiopyrans is due not to specific orbital interactions but to steric strains in the molecule.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 576–582, March, 1986.
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Aldoshin, S.M., Kholmanskii, A.S. & Atovmyan, L.O. Effect of the nature of the heteroatoms at the spiro unit of indoline spiropyrans on their structure and photochemical characteristics. Russ Chem Bull 35, 523–528 (1986). https://doi.org/10.1007/BF00953219
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DOI: https://doi.org/10.1007/BF00953219