Exciplex and excimer molecular probes: detection of conformational flip in a myo-inositol chair

Manikandan Kadirvel, Biljana Arsic, Sally Freeman, Elena V. Bichenkova

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

2-O-tert-Butyldimethylsilyl-4,6-bis-O-pyrenoyl-myo-inositol-1,3, 5-orthoformate (6) and 2-O-tert-butyldimethylsilyl-4-O-[4-(dimethylamino) benzoyl]-6-O-pyrenoyl-myo-inositol-1,3,5-orthoacetate (10) adopt conformationally restricted unstable chairs with five axial substituents. In the symmetrical diester 6, the two π-stacked pyrenoyl groups are electron acceptor-donor partners, giving a strong intramolecular excimer emission. In the mixed ester 10, the pyrenoyl group is the electron acceptor and the 4-(dimethylamino)benzoyl ester is the electron donor, giving a strong intramolecular exciplex emission. The conformation of the mixed ester 10 was assessed using 1H NMR spectroscopy (1H-NOESY) and computational studies. which showed the minimum inter-centroid distance between the two aromatic systems to be ∼3.9 Å Upon addition of acid, the orthoformate/orthoacetate trigger in 6and 10 was cleaved, which caused a switch of the conformation of the myo-inositol ring to the more stable penta-equatorial chair, leading to separation of the aromatic ester groups and loss of excimer and exciplex fluorescence, respectively. This study provides proof of principle for the development of novel fluorescent molecular probes.

Original languageEnglish
Pages (from-to)1966-1972
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume6
Issue number11
DOIs
Publication statusPublished - 9 Apr 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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