Synthesis and optical characterization of novel enantiopure BODIPY linked azacrown ethers as potential fluorescent chemosensors

Ildikó Móczár, P. Huszthy, Zita Maidics, Mihály Kádár, Tóth Klára Tóth

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Two novel enantiopure BODIPY linked azacrown ether chemosensors were prepared by reacting 3-chloro-5-methoxyBODIPY with new enantiopure monoaza-18-crown-6 ether ligands bearing two methyl and isobutyl groups on their chiral centres, respectively. The latter compounds were synthesized starting from optically active tetraethylene glycols in six steps. The operation of chemosensors is based on the intramolecular charge transfer (ICT) process. They exhibit pronounced off-on type fluorescent responses to some metal ions and chiral primary aralkyl ammonium ions, in particular to Ca2+ and Pb2+. Even in the case of 1:1 ratio of Ca2+ and Pb2+ ions to the ionophores, the fluorescence intensities and quantum yield values increased more than 10-fold, as well as both the absorption and emission bands were blue-shifted by about 20-30 nm (hipsochromic effect) in acetonitrile. The formation of relatively stable complexes allowed the determination of log Ks values by the mole-ratio method.

Original languageEnglish
Pages (from-to)8250-8258
Number of pages9
JournalTetrahedron
Volume65
Issue number39
DOIs
Publication statusPublished - Sep 26 2009

Fingerprint

Ethers
Ether
Bearings (structural)
Ions
Glycols
Ionophores
Quantum yield
Ammonium Compounds
Crown Ethers
Metal ions
Charge transfer
Fluorescence
Ligands
Metals
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
acetonitrile
18-crown-6

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and optical characterization of novel enantiopure BODIPY linked azacrown ethers as potential fluorescent chemosensors. / Móczár, Ildikó; Huszthy, P.; Maidics, Zita; Kádár, Mihály; Klára Tóth, Tóth.

In: Tetrahedron, Vol. 65, No. 39, 26.09.2009, p. 8250-8258.

Research output: Contribution to journalArticle

Móczár, Ildikó ; Huszthy, P. ; Maidics, Zita ; Kádár, Mihály ; Klára Tóth, Tóth. / Synthesis and optical characterization of novel enantiopure BODIPY linked azacrown ethers as potential fluorescent chemosensors. In: Tetrahedron. 2009 ; Vol. 65, No. 39. pp. 8250-8258.
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