Photochromism in cucurbit[8]uril cavity

Inhibition of hydrolysis and modification of the rate of merocyanine-spiropyran transformations

Research output: Article

28 Citations (Scopus)

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

Fingerprint

Photochromism
photochromism
hydrolysis
Hydrolysis
cavities
Equilibrium constants
Complexation
Encapsulation
Reaction kinetics
Isomers
water
Water
reaction kinetics
isomers
Dyes
Activation energy
dyes
inclusions
activation energy
aqueous solutions

ASJC Scopus subject areas

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

Cite this

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title = "Photochromism in cucurbit[8]uril cavity: Inhibition of hydrolysis and modification of the rate of merocyanine-spiropyran transformations",
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.",
author = "Z. Miskolczy and L. Bicz{\'o}k",
year = "2011",
month = "11",
day = "3",
doi = "10.1021/jp207708x",
language = "English",
volume = "115",
pages = "12577--12583",
journal = "Journal of Physical Chemistry B Materials",
issn = "1520-6106",
publisher = "American Chemical Society",
number = "43",

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TY - JOUR

T1 - Photochromism in cucurbit[8]uril cavity

T2 - Inhibition of hydrolysis and modification of the rate of merocyanine-spiropyran transformations

AU - Miskolczy, Z.

AU - Biczók, L.

PY - 2011/11/3

Y1 - 2011/11/3

N2 - 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.

AB - 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.

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U2 - 10.1021/jp207708x

DO - 10.1021/jp207708x

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JO - Journal of Physical Chemistry B Materials

JF - Journal of Physical Chemistry B Materials

SN - 1520-6106

IS - 43

ER -