Quantitative investigations of cation complexation of photochromic 8-benzothiazole-substituted benzopyran: towards metal-ion sensors

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Marianna I ZakharovaVladimir I Minkin

Abstract

The photochromic, thermochromic and metallochromic behaviour of a series of three spiro[indoline-8-(benzothiazol-2-yl)-benzopyrans] has been investigated. The thermodynamic and kinetic parameters of their thermal equilibrium between the ring-closed (spiro) and ring-opened (merocyanine) isomeric forms have been determined using UV-Vis absorption and (1)H NMR spectroscopies. By adding Co(ii) and Ni(ii) ions in acetonitrile solution, 1 : 1 and 1 : 2 metal : merocyanine complexes are formed simultaneously. Using appropriate numerical methods, the kinetic analysis of the complexation allowed us to determine accurately key thermodynamic and spectroscopic parameters of the metal complexes. Results showed that the complexation strength is very sensitive to the size of the indoline nitrogen substituent. Complexation can be reversed by shining white light on the coloured complexes which regenerates the inactive spiropyran form, and releases the metallic ion; hence, these systems display fully reversible negative photochromism. The Zn(ii) complexes exhibit intense fluorescence in the 600-800 nm wavelength range. All these behaviours make these spiropyrans bearing benzothiazole heterocycles promising building blocks for the future construc...Continue Reading

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Citations

Jul 23, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aurélie PlaquetFrédéric Castet
Aug 21, 2010·Biosensors & Bioelectronics·Robert ByrneDermot Diamond
Oct 29, 2014·Chemistry, an Asian Journal·Ajit Kumar MahapatraSabyasachi Sarkar
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Oct 1, 2010·Physical Chemistry Chemical Physics : PCCP·Edith BotekJean-Louis Habib-Jiwan
Aug 29, 2017·Beilstein Journal of Organic Chemistry·Alexis Perry, Christina J Kousseff
May 29, 2020·Beilstein Journal of Organic Chemistry·Phil M PithanHeiko Ihmels
Jan 22, 2019·Journal of the American Chemical Society·Eric S EpsteinPaul V Braun
Nov 6, 2013·The Journal of Physical Chemistry. a·Audrey SégerieYi Luo
Oct 28, 2019·Inorganic Chemistry·Thomas J FeuersteinPeter W Roesky
May 3, 2012·Journal of the American Chemical Society·Benoît ChampagneFrédéric Castet

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