Synthesis and Conformational Switching of Partially and Differentially Bridged Resorcin[4]arenes Bearing Fluorescent Dye Labels. Preliminary Communication

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Abstract

We report the synthesis of modified Cram-type cavitands bearing one or two fluorescent labels for single-molecule spectroscopic studies of vase[BOND]kite conformational switching (Scheme 3). Syntheses were performed by stepwise bridging of the four couples of neighboring H-bonded OH groups of resorcin[4]arene bowls (Schemes 2 and 3). The new substitution patterns enable the construction of a large variety of future functional architectures. 1H-NMR Investigations showed that the new partially and differentially bridged cavitands feature temperature- and pH-triggered vase[BOND]kite conformational isomerism similar to symmetrical cavitands with four identical quinoxaline bridges (Table). It was discovered that vase[BOND]kite switching of cavitands is strongly solvent-dependent.

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