1,3-indane-based chromogenic calixpyrroles with push-pull chromophores: synthesis and anion sensing

Ryuhei Nishiyabu; Pavel Anzenbacher Jr

doi:10.1021/ol0521782

1,3-indane-based chromogenic calixpyrroles with push-pull chromophores: synthesis and anion sensing

Org Lett. 2006 Feb 2;8(3):359-62. doi: 10.1021/ol0521782.

Authors

Ryuhei Nishiyabu¹, Pavel Anzenbacher Jr

Affiliation

¹ Center for Photochemical Sciences and Department of Chemistry, Bowling Green State University, Bowling Green, Ohio 43403, USA.

PMID: 16435834
DOI: 10.1021/ol0521782

Abstract

[structure: see text]. Knoevenagel condensation of 2-formyl-octamethylcalix[4]pyrrole with selected 1,3-indanedione derivatives yields calix[4]pyrrole anion sensors with push-pull chromophores displaying strong intramolecular charge transfer. The push-pull feature results in augmented signal output as well as in dramatic changes in anion selectivity exemplified by a 50-fold increase in acetate vs chloride selectivity compared to the parent calix[4]pyrrole.