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Abstract
Molecular structures of a novel carotenoid analogue, 2-(all-trans-retinylidene)-indan-1,3-dione (RetInd), were determined in solution and in the crystalline state by 1H-NMR spectroscopy and by X-ray crystallography, respectively. They were compared with those of all-trans-retinal (Ret), a visual chromophore. Ret takes a 6s-cis configuration (a cis configuration around the C6–C7 single bond) that is usually found in carotenoid analogues that have β-end groups, both in solution and in the crystalline state. On the other hand, it was found that RetInd took a 6s-cis configuration in solution but it took a 6s-trans configuration in the crystalline state. Comparison of the crystallographic structures between Ret and RetInd lead us to the conclusion that a van der Waals attraction in polyene chains and steric repulsion between a cyclohexene and an indan-1,3-dione ring stabilized the 6s-trans configuration of RetInd in the crystalline state.
Published Version
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