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Role of Ring Ortho Substituents on the Configuration of Carotenoid Polyene Chains

Author(s):

Minsoo Kim, Hyunuk Jung, Albert C. Aragonès, Ismael Díez-Pérez, Kwang-Hyun Ahn, Wook-Jin Chung, Dahye Kim, Sangho Koo

Journal:

Organic Letters

Year:

2018

Volume:

20

Pages

493-496

DOI:

10.1021/acs.orglett.7b03930

Abstract:

The 9-(Z)-configuration was exclusively obtained in the carotenoid polyene chain irrespective of olefination and disconnection methods for terminal ortho-unsubstituted benzene rings. The 2,6-dimethyl substituents in the terminal rings secure an all-(E)-polyene structure. The single molecular conductance of the pure 9-(Z)-carotene was measured for the first time to be 1.53 × 10−4 ± 6.37 × 10−5 G0, whose value was 47% that of the all-(E)-carotene ((3.23 × 10−4 ) ± (1.23 × 10−4 ) G0).

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