Article,

Synthesis and Conformational Switching of Partially and Differentially Bridged Resorcin4arenes Bearing Fluorescent Dye Labels

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Helv. Chim. Acta, 86 (6): 2149-2155 (Jul 10, 2003)
DOI: 10.1002/hlca.200390172

Abstract

We report the synthesis of modified Cram-type cavitands bearing one or two fluorescent labels for single-molecule spectroscopic studies of vase-kite conformational switching. Syntheses were performed by stepwise bridging of the four couples of neighboring H-bonded OH groups of resorcin4arene bowls. The new substitution patterns enable the construction of a large variety of future functional architectures. H-NMR Investigations showed that the new partially and differentially bridged cavitands feature temperature- and pH-triggered vase-kite conformational isomerism similar to symmetrical cavitands with four identical quinoxaline bridges. It was discovered that vase-kite switching of cavitands is strongly solvent-dependent.

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