Synthesis, characterization and cation-induced isomerization of photochromic calix[4](aza)crown-indolospiropyran conjugates

A. Grün, Péter Kerekes, I. Bitter

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Calix[4](aza)crown-5, -6 and -7 ionophores in cone and 1,3-alt conformation carrying photochromic indolospirobenzopyran (SP) signalling group were synthesized and their cation-induced isomerization to the colored merocyanine (Mc) form was studied by UV/vis spectroscopy in the presence of mono-and divalent metal ions. Under dark conditions the SP-Mc equilibrium was remarkably shifted to the colored Mc form by cations of high positive charge density (alkaline earth metal ions), and it was affected by some transition metal ions (Cu2+, Zn2+ and Pb2+) as well. Generally, the extent of isomerization of the cone conformers was larger than that of the 1,3-alt counterparts. The chelation-induced reaction was evaluated by calculating the rate constants of the coloration process.

Original languageEnglish
Pages (from-to)255-263
Number of pages9
JournalSupramolecular Chemistry
Volume20
Issue number3
DOIs
Publication statusPublished - Apr 2008

Fingerprint

Isomerization
Metal ions
Cations
Cones
Alkaline Earth Metals
Ionophores
Chelation
Charge density
Ultraviolet spectroscopy
Transition metals
Conformations
Rate constants
merocyanine

Keywords

  • Calix[4](aza)crowns
  • Cation recognition
  • Indolospiropyrans
  • Isomerization

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis, characterization and cation-induced isomerization of photochromic calix[4](aza)crown-indolospiropyran conjugates. / Grün, A.; Kerekes, Péter; Bitter, I.

In: Supramolecular Chemistry, Vol. 20, No. 3, 04.2008, p. 255-263.

Research output: Contribution to journalArticle

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