Locked Energy of Axial to Equatorial Transformation Monitored by Exciplex and Excimer Fluorescence

• Manikandan Kadirvel

  School of Pharmacy and Pharmaceutical Sciences, University of Manchester

• Elena V Bichenkova

  School of Pharmacy and Pharmaceutical Sciences, University of Manchester

• Antony D’Emanuele

  School of Pharmacy and Pharmaceutical Sciences, University of Manchester

• Sally Freeman

  School of Pharmacy and Pharmaceutical Sciences, University of Manchester

Abstract

2-O-tert-Butyldimethylsilyl-4,6-bispyrenoyl-myo-inositol-1,3,5-orthoformate (1) and 2-O-tert-butyldimethylsilyl-4-[(4-dimethylamino)benzoyl]-6-pyrenoyl-myo-inositol-1,3,5-orthoacetate (2) adopt unstable chair conformations with five substituents axial, in which the aromatic esters participate in π-stacking, and give excimer and exciplex fluorescence, respectively. Upon addition of acid, the orthoformate/orthoacetate lock is cleaved, which allows the inositol ring to switch to the more stable penta-equatorial chair conformation, with loss of exciplex/excimer fluorescence.

Journal

• Chemistry Letters

  Chemistry Letters 35 (8), 868-869, 2006-07-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360283694087590656
• NII Article ID: 10018187437
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2006.868
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/35/8/868/55591787/cl.2006.868.pdf
• Data Source:
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  • CiNii Articles