Pyreno[2,1-b]pyrrole and Bis(pyreno[2,1-b]pyrrole) as Selective Chemosensors of Fluoride Ion:  A Mechanistic Study

Chia-I Lin,† Srinivasan Selvi,† Jim-Min Fang,*†‡ Pi-Tai Chou,*† Chin-Hung Lai, and Yi-Ming Cheng;
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan, and The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan
J. Org. Chem., 2007, 72 (9), pp 3537–3542
DOI: 10.1021/jo070169w
Publication Date (Web): March 28, 2007
Copyright © 2007 American Chemical Society
†

 National Taiwan University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 The Genomics Research Center.

, jmfang@ntu.edu.tw, ; , chop@ntu.edu.tw

Abstract

Abstract Image

Pyreno[2,1-b]pyrrole and its dimeric derivative display excellent selectivity and sensitivity for detection of fluoride ion, in comparison with chloride, bromide, iodide, acetate, dihydrogen phosphate, hydrogen sulfate, perchlorate, nitrate, and thiocyanate ions. The hydrogen bonding with fluoride ion, both in formation and in subsequent dissociation, provides remarkable colorimetric and fluorescent changes in the visible region that are advantageous for real-time and on-site application. Detailed NMR and dynamic fluorescence spectroscopic analyses establish the associated mechanism.

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History

  • Published In Issue April 27, 2007
  • Received January 29, 2007

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