Journal
HELVETICA CHIMICA ACTA
Volume 86, Issue 6, Pages 2149-2155Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.200390172
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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 (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. H-1-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 (Table). It was discovered that vase-kite switching of cavitands is strongly solvent-dependent.
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