15-Stibaindoles as Lewis Acidic, -Conjugated, Fluoride Anion Responsive Platforms uri icon

abstract

  • 2017 American Chemical Society. Our interest in anion-responsive materials has led us to investigate the synthesis and properties of derivatives featuring a Lewis acidic antimony(V) moiety integrated within the -conjugated structure of a 15-stibaindole (or 15-benzostibole). Starting from an organozirconium reagent, 1,2,3-tris(phenyl)-1-stibaindole (1) was first synthesized and subsequently allowed to react with o-chloranil and 3,5-di-tert-butyl-o-benzoquinone to afford the corresponding catecholato-15-stibaindole derivatives 2 and 3, respectively, as a result of oxidative addition of the o-benzoquinone reagent to the antimony center. Conversion of 1 into 2 and 3 lowers the energy of the antimony-based orbital, thus promoting its conjugation with the orbital of the heterocyclic chromophore. As a result of this - conjugation, 2 and 3 experience a narrowing of the - energy gap leading to a red shift of the corresponding UV-vis absorption band. This - conjugation can be turned off by addition of a fluoride anion, which interacts with the antimony-based orbital. This turn-off response manifests itself in a color change that can be exploited for the detection of ppm levels of fluoride in drinking water samples.

published proceedings

  • ORGANOMETALLICS

altmetric score

  • 4.35

author list (cited authors)

  • Christianson, A. M., Rivard, E., & Gabbai, F. P.

citation count

  • 47

complete list of authors

  • Christianson, Anna M||Rivard, Eric||Gabbaii, Francois P

publication date

  • July 2017