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

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(-), HSO4(-), CH3COO(-), H2PO4(-), and HP2O7(3-), was tested in organic media by monitoring the changes in their UV/vis and (1)H 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.

SUBMITTER: Lee MH

PROVIDER: S-EPMC3133693 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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

Lee Min Hee MH Cao Qian-Yong QY Kim Sung Kuk SK Sessler Jonathan L JL Kim Jong Seung JS

The Journal of organic chemistry 20101231 3

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(-), HSO4(-), CH3COO(-), H2PO4(-), and HP2O7(3-), was tested in organic media by monitoring the changes in their UV/vis and (1)H NMR spectra as a function of added anion, as well as via cyclovoltammetry (CV) ...[more]

PMID: 21194202

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Correction: Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space.

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