Synthesis and studies of new photochromic spiropyrans containing a formylcoumarin fragment
- Authors: Nikolaeva O.G.1, Metelitsa A.V.1, Cheprasov A.S.2, Karlutova O.Y.1, Starikov A.G.2, Dubonosov A.D.2, Bren´ V.A.1, Minkin V.I.1,2
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Affiliations:
- Institute of Physical and Organic Chemistry, Southern Federal University
- Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova
- Issue: Vol 65, No 4 (2016)
- Pages: 944-951
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/237767
- DOI: https://doi.org/10.1007/s11172-016-1396-x
- ID: 237767
Cite item
Abstract
A computer search for new photoactive compounds among indoline spiropyrans of coumarin series was carried out using DFT B3LYP/6-31G(d,p) method. Based on the data obtained, the spiropyrans containing a formylcoumarin fragment annulated to the 2H-pyran ring and possessing photochromic properties were synthesized. The structure and photochromism of these compounds were studied by 1H NMR, IR, and UV/Vis spectroscopy. The introduction of a formyl group into the coumarin moiety of spiropyrans led to a bathochromic shift of the long wavelength absorption maxima of merocyanine isomers, as well as to a considerable increase in their lifetime.
About the authors
O. G. Nikolaeva
Institute of Physical and Organic Chemistry, Southern Federal University
Email: aled@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
Email: aled@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
A. S. Cheprasov
Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov on Don, 344006
O. Yu. Karlutova
Institute of Physical and Organic Chemistry, Southern Federal University
Email: aled@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
A. G. Starikov
Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov on Don, 344006
A. D. Dubonosov
Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova
Author for correspondence.
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov on Don, 344006
V. A. Bren´
Institute of Physical and Organic Chemistry, Southern Federal University
Email: aled@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090
V. I. Minkin
Institute of Physical and Organic Chemistry, Southern Federal University; Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova
Email: aled@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov on Don, 344090; Rostov on Don, 344006