Display options
Share it on

Org Lett. 2015 Sep 04;17(17):4140-3. doi: 10.1021/acs.orglett.5b01866. Epub 2015 Aug 27.

Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion.

Organic letters

Ritwik Samanta, B Sathish Kumar, Pradeepta K Panda

Affiliations

  1. School of Chemistry and ‡Advanced Centre of Research in High Energy Materials, University of Hyderabad , Hyderabad 500046, India.

PMID: 26313641 DOI: 10.1021/acs.orglett.5b01866

Abstract

Four new calix[4]pyrroles with the shortest possible strap so far through ortho-linking of the aromatic unit have been synthesized, including a naphthalene-derived fluorescent receptor. They show exclusive selectivity toward the fluoride ion as confirmed by (1)H NMR, isothermal titration calorimetry, and fluorescence spectroscopic study. Anion affinity could also be modulated further via functionalization at the strap. Computational analysis displays calix[4]pyrroles binding to fluoride ion in a very unusual 1,3-alternate conformation where the anion resides on the opposite side of the strap.

Publication Types