Anion responsive TTF-appended calix[4]arenes. synthesis and study of two different conformers

Min Hee Lee, Qian Yong Cao, Sung Kuk Kim, Jonathan L. Sessler, Jong Seung Kim

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Two new cone- and 1,3-alternate-calix[4]arenes (cone-1 and 1,3-alt-1), bearing four modified TTF (tetrathiafulvalene) substituents on the upper rim, have been synthesized. The binding ability of these two sets of conformers for various anions, including F-, Cl-, Br-, I -, PF6-, ClO4-, HSO 4-, CH3COO-, H2PO 4-, and HP2O7 3 -, was tested in organic media by monitoring the changes in their UV/vis and 1H NMR spectra as a function of added anion, as well as via cyclovoltammetry (CV) (all anions studied as their respective TBA salts). On the basis of the present findings, we propose that incorporation of four TTF units within an overall calix[4]arene-based recognition framework produces a preorganized receptor system that displays a modest preference for the pyrophosphate (HP2O7 3-)anion.

Original languageEnglish
Pages (from-to)870-874
Number of pages5
JournalJournal of Organic Chemistry
Volume76
Issue number3
DOIs
Publication statusPublished - 2011 Feb 4

ASJC Scopus subject areas

  • Organic Chemistry

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