Reversible double-helix-random-coil transition process of bis{hexa(ethynylhelicene)}s

Chemistry, an Asian Journal
Hiroki SugiuraMasahiko Yamaguchi

Abstract

Two compounds with two hexa(ethynylhelicene) parts connected by a flexible hexadecamethylene and a rigid butadiyne linker were synthesized. The 1H NMR spectroscopic and CD analyses and vapor-pressure osmometry (VPO) of these two compounds revealed intramolecular double-helix formation. Upon heating a 5-microM solution in toluene, the double-helix structure unfolded to form a random coil, and on cooling it folded again into a double helix. The thermodynamic stabilities of both structures were dependent on temperature, and the structural change in both compounds is due to the large enthalpies and entropies under equilibrium. The rate constants of their unfolding were obtained by assuming a pseudo-first-order reaction; the compound with a rigid linker unfolded slower than that with a flexible linker. The former has a larger activation energy, and its double-helix and random-coil conformers were separated by chromatography. The rate of folding was also faster for the flexible-linker compound with larger activation energy. The rate constants for the folding of both compounds slightly decreased with increasing temperature, which was ascribed to the presence of exothermic pre-equilibrium and rate-determining steps. The folding was mar...Continue Reading

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Citations

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