Spiropyrans and spirooxazines 13. Synthesis and photochromic properties of benzoxazolyl-substituted spirobenzopyrans
- Authors: Rostovtseva I.A.1, Voloshin N.A.1, Solov’eva E.V.1, Chernyshev A.V.1, Metelitsa I.A.1, Metelitsa A.V.1
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Affiliations:
- Institute of Physical and Organic Chemistry, Southern Federal University
- Issue: Vol 67, No 8 (2018)
- Pages: 1476-1481
- Section: Article
- URL: https://journals.rcsi.science/1066-5285/article/view/242837
- DOI: https://doi.org/10.1007/s11172-018-2242-0
- ID: 242837
Cite item
Abstract
New benzoxazolyl-substituted spiroindoline-benzopyrans with electron-withdrawing groups in the indoline fragment were obtained. These compounds exhibit positive P- and T-type photochromism. Structural correlations of the spectrokinetic properties depending on the variation of substituents in the indoline part of the spiropyran molecules were established. Electronwithdrawing groups were found to cause a bathochromic shift of the long-wavelength absorption maxima of the merocyanine isomers as compared to the unsubstituted spiropyran and decrease their lifetime. Conversely, an introduction of electron-donating groups results in a hypso chromic shift of the absorption maxima and an increase in the lifetime of the colored isomers of spiropyrans. Electron-withdrawing substituents at the position 5 of the indoline fragment cause the increase of the colorability of the spiropyrans.
About the authors
I. A. Rostovtseva
Institute of Physical and Organic Chemistry, Southern Federal University
Email: met@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
N. A. Voloshin
Institute of Physical and Organic Chemistry, Southern Federal University
Email: met@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
E. V. Solov’eva
Institute of Physical and Organic Chemistry, Southern Federal University
Email: met@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
A. V. Chernyshev
Institute of Physical and Organic Chemistry, Southern Federal University
Email: met@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
I. A. Metelitsa
Institute of Physical and Organic Chemistry, Southern Federal University
Email: met@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
A. V. Metelitsa
Institute of Physical and Organic Chemistry, Southern Federal University
Author for correspondence.
Email: met@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090