PHOTOCHROMIC AND THERMOCHROMIC SPIRANES. 33. SYNTHESIS OF A NEW INDOLINONAPHTHOXAZINOBISSPIROPYRAN AND INVESTIGATION OF ITS PHOTOCHROMIC CHARACTERISTICS

Authors

  • Е. Л. Муханов Research Institute of Physical and Organic Chemistry, Southern Federal University
  • Ю. С. Алексеенко Southern Scientific Center, Russian Academy of Sciences
  • И. В. Дороган Research Institute of Physical and Organic Chemistry, Southern Federal University
  • В. В. Ткачев Institute of Problems of Chemical Physics, Russian Academy of Sciences
  • Б. С. Лукьянов Research Institute of Physical and Organic Chemistry, Southern Federal University
  • С. М. Алдошин Institute of Problems of Chemical Physics, Russian Academy of Sciences
  • С. О. Безуглый Southern Scientific Center, Russian Academy of Sciences
  • В. И. Минкин Research Institute of Physical and Organic Chemistry, Southern Federal University
  • А. Н. Утенышев Institute of Problems of Chemical Physics, Russian Academy of Sciences
  • О. Н. Рящин Research Institute of Physical and Organic Chemistry, Southern Federal University

DOI:

https://doi.org/10.1007/2833

Keywords:

bisspiropyran, merocyanine, TD DFT, photochromism

Abstract

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.

How to Cite
Mukhanov, E. L.; Alekseenko, Yu. S.; Dorogan, I. V.; Tkachev, V. V.; Lukyanov, B. S.; Aldoshin, S. M.; Bezuglyi, S. O.; Minkin, V. I.; Utenyshev, A. N.; Ryashchin, O. N. Chem. Heterocycl. Compd. 2010, 46, 279. [Khim. Geterotsikl. Soedin. 2010, 357.]

For this article in the English edition see DOI 10.1007/s10593-010-0503-4

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Published

2015-12-03

Issue

No. 3 (2010)

Section

Original Papers