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Photo‐ and thermochromic cation sensitive spiro[indoline‐pyridobenzopyrans]
Author(s) -
Chernyshev Anatoly V.,
Metelitsa Anatoly V.,
Gaeva Elena B.,
Voloshin Nikolai A.,
Borodkin Gennady S.,
Minkin Vladimir I.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1252
Subject(s) - chemistry , merocyanine , indoline , thermochromism , spiropyran , photochemistry , ring (chemistry) , photochromism , metal ions in aqueous solution , metal , stereochemistry , organic chemistry
The photo‐ and thermochromic behaviour of a series of spiro[indolinepyridobenzopyrans] 1–5 has been studied. The thermodynamic and kinetic parameters of the thermal equilibria between the ring‐closed and ring‐opened (merocyanine) isomeric forms of spiropyrans have been determined using UV–Vis absorption and 1 H NMR spectroscopies techniques. The most stable form of 1‐(2‐hydroxyethyl)‐spiro[indoline‐pyridobenzopyran] 4 is represented by its trans ‐(hydroxystyryl)oxazolidineindoline isomer coexisting in acetone solution with the ring‐closed spiroform. In the presence in solution of metal salts, spiro[indoline‐pyridobenzopyrans] exhibit strong ionochromic effect due to the formation of complexes with the merocyanine ligand. The composition of the complexes formed by Zn 2+ and Ni 2+ ions has been determined with the use of spectrophotometric and electrospray ionisation mass spectroscopy techniques. The stepwise stability constants and spectral properties of the most stable 1:1 and 1:2 metal/merocyanine complexes have been determined. Selectivity of the complexation reaction depends on the position of the thermochromic equilibrium. Copyright © 2007 John Wiley & Sons, Ltd.