Trans-cis Photoisomerization of 1-Methyl-4-(4′-hydroxystyryl)pyridinium in inclusion complexes of β-cyclodextrin and its derivatives

Keita Hamasaki, Asao Nakamura, Akihiko Ueno, Fujio Toda

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4 Citations (Scopus)

Abstract

The effects of β-cyclodextrin (β-CyD), heptakis(2,6-di-O-methyl)-β-cyclodextrin (DMβCyD) and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCyD) on trans-cis photoisomerization of 1-ethyl-4-(4′-hydroxystyryl)pyridinium (POH) have been studied in aqueous solutions. The ratio of [cis]/[trans] for POH in the photostationary state at pH 8.54 was remarkably reduced by the presence of βCyD or DMβCyD. The reduction of the [cis]/[trans] ratio in the photostationary state was explained in terms of the shift of the equilibrium of POH+trans ⇌ POtrans + H- toward POtrans formation. The binding constants of βCyD and DMβCyD for POtrans were 2.00- and 1.36-fold larger than those for POH+trans, respectively. The binding constants of TMβCyD for both species are much smaller than those of βCyD and DMβCyD. This result indicates that POtrans, which has a betain structure, forms stable complexes with βCyD and DMβCyD with its hydrophobic parts inside and the charged parts outside the CyD cavities.

Original languageEnglish
Pages (from-to)349-359
Number of pages11
JournalJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume13
Issue number4
DOIs
Publication statusPublished - 1992 Aug
Externally publishedYes

Fingerprint

Photoisomerization
cyclodextrins
Cyclodextrins
chemical derivatives
inclusions
aqueous solutions
cavities
shift

Keywords

  • 1-methyl-4-(4′-hydroxystyryl)pyridinium
  • betain
  • charge separation
  • cyclodextrin
  • inclusion complex
  • trans-cis photoisomerization

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Chemistry(all)

Cite this

@article{1626f0dedc9944c4b66bd341c547134a,
title = "Trans-cis Photoisomerization of 1-Methyl-4-(4′-hydroxystyryl)pyridinium in inclusion complexes of β-cyclodextrin and its derivatives",
abstract = "The effects of β-cyclodextrin (β-CyD), heptakis(2,6-di-O-methyl)-β-cyclodextrin (DMβCyD) and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCyD) on trans-cis photoisomerization of 1-ethyl-4-(4′-hydroxystyryl)pyridinium (POH) have been studied in aqueous solutions. The ratio of [cis]/[trans] for POH in the photostationary state at pH 8.54 was remarkably reduced by the presence of βCyD or DMβCyD. The reduction of the [cis]/[trans] ratio in the photostationary state was explained in terms of the shift of the equilibrium of POH+trans ⇌ POtrans + H- toward POtrans formation. The binding constants of βCyD and DMβCyD for POtrans were 2.00- and 1.36-fold larger than those for POH+trans, respectively. The binding constants of TMβCyD for both species are much smaller than those of βCyD and DMβCyD. This result indicates that POtrans, which has a betain structure, forms stable complexes with βCyD and DMβCyD with its hydrophobic parts inside and the charged parts outside the CyD cavities.",
keywords = "1-methyl-4-(4′-hydroxystyryl)pyridinium, betain, charge separation, cyclodextrin, inclusion complex, trans-cis photoisomerization",
author = "Keita Hamasaki and Asao Nakamura and Akihiko Ueno and Fujio Toda",
year = "1992",
month = "8",
doi = "10.1007/BF01133234",
language = "English",
volume = "13",
pages = "349--359",
journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",
issn = "1388-3127",
publisher = "Kluwer Academic Publishers",
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}

TY - JOUR

T1 - Trans-cis Photoisomerization of 1-Methyl-4-(4′-hydroxystyryl)pyridinium in inclusion complexes of β-cyclodextrin and its derivatives

AU - Hamasaki, Keita

AU - Nakamura, Asao

AU - Ueno, Akihiko

AU - Toda, Fujio

PY - 1992/8

Y1 - 1992/8

N2 - The effects of β-cyclodextrin (β-CyD), heptakis(2,6-di-O-methyl)-β-cyclodextrin (DMβCyD) and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCyD) on trans-cis photoisomerization of 1-ethyl-4-(4′-hydroxystyryl)pyridinium (POH) have been studied in aqueous solutions. The ratio of [cis]/[trans] for POH in the photostationary state at pH 8.54 was remarkably reduced by the presence of βCyD or DMβCyD. The reduction of the [cis]/[trans] ratio in the photostationary state was explained in terms of the shift of the equilibrium of POH+trans ⇌ POtrans + H- toward POtrans formation. The binding constants of βCyD and DMβCyD for POtrans were 2.00- and 1.36-fold larger than those for POH+trans, respectively. The binding constants of TMβCyD for both species are much smaller than those of βCyD and DMβCyD. This result indicates that POtrans, which has a betain structure, forms stable complexes with βCyD and DMβCyD with its hydrophobic parts inside and the charged parts outside the CyD cavities.

AB - The effects of β-cyclodextrin (β-CyD), heptakis(2,6-di-O-methyl)-β-cyclodextrin (DMβCyD) and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCyD) on trans-cis photoisomerization of 1-ethyl-4-(4′-hydroxystyryl)pyridinium (POH) have been studied in aqueous solutions. The ratio of [cis]/[trans] for POH in the photostationary state at pH 8.54 was remarkably reduced by the presence of βCyD or DMβCyD. The reduction of the [cis]/[trans] ratio in the photostationary state was explained in terms of the shift of the equilibrium of POH+trans ⇌ POtrans + H- toward POtrans formation. The binding constants of βCyD and DMβCyD for POtrans were 2.00- and 1.36-fold larger than those for POH+trans, respectively. The binding constants of TMβCyD for both species are much smaller than those of βCyD and DMβCyD. This result indicates that POtrans, which has a betain structure, forms stable complexes with βCyD and DMβCyD with its hydrophobic parts inside and the charged parts outside the CyD cavities.

KW - 1-methyl-4-(4′-hydroxystyryl)pyridinium

KW - betain

KW - charge separation

KW - cyclodextrin

KW - inclusion complex

KW - trans-cis photoisomerization

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