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SYNTHESIS OF BIS-SPIROPYRANS BASED ON 6,8-DIFORMYL-5,7-DIHYDROXY- 4 METHYLCOUMARIN AND PHOTOCHROMIC PROPERTIES THEREOF

Ольга Г. Николаева, Ольга Ю. Карлутова, Александр С. Чепрасов, Анатолий В. Метелица, Игорь В. Дороган, Александр Д. Дубоносов, Владимир А. Брень
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Abstract


Synthesis of new asymmetric bis-spiropyrans of indoline series based on 6,8-diformyl-5,7-dihydroxy-4-methylcoumarin was realized. Depending on the nature of the substituents in positions 1 and 5 of the indoline moiety the derived compounds may exist in solution in the spiro or merocyanine forms, or as a tautomeric mixture of these forms. UV irradiation of the cyclic forms leads to photocoloring associated with re-opening of one or both of the spiro moieties. The wide variability of spectral kinetic properties of bis-spiropyrans upon fluorescence of photoinduced forms allows one to consider them as molecular switches having absorptive and fluorescent signal functions with the possibility of practical application.

How to Cite
Nikolaeva, O. G.; Karlutova, O. Yu.; Cheprasov, A. S.; Metelitsa, A. V.; Dorogan, I. V.; Dubonosov, A. D.; Bren', V. A. Chem. Heterocycl. Compd. 2015, 51, 229. [Khim. Geterotsikl. Soedin. 2015, 51, 229.]

For this article in the English edition see DOI 10.1007/s10593-015-1689-2

 


Keywords


6,8-diformyl-5,7-dihydroxy-4-methylcoumarin; merocyanine; spiropyran; quantum-chemical calculations; photochromism

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