Photochromism in cucurbit[8]uril cavity: Inhibition of hydrolysis and modification of the rate of merocyanine-spiropyran transformations

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Abstract

The effect of inclusion complex formation on the photochromic behavior of a spirobenzopyran dye and its merocyanine isomer was studied in aqueous solution using cucurbit[8]uril (CB8) as a host. The merocyanine (MC) and protonated merocyanine (MCH+) were the most stable forms both in water and inside the cavity of CB8. The equilibrium constant of 1:1 complexation with CB8 was found to be 1.7 × 105 and 2.0 × 106 M -1 for the former and latter species, respectively. The encapsulation led to significant change in the rate of the photoinduced and thermal photochromic transformations and hindered the hydrolysis of MC. The effect of CB8 on the reaction kinetics strongly altered with pH. The transition from the spiropyran form to trans-MC in a thermal reaction had 33 kJ mol-1 lower activation energy and more than 5 orders of magnitude smaller Arrhenius pre-exponential factor in CB8 than in water.

Original languageEnglish
Pages (from-to)12577-12583
Number of pages7
JournalJournal of Physical Chemistry B
Volume115
Issue number43
DOIs
Publication statusPublished - nov. 3 2011

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry

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