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

M. Kim; H. Jung; A.C. Aragonès; I. Díez-Pérez; K.-H. Ahn; W.-J. Chung; D. Kim; S. Koo

doi:10.1021/acs.orglett.7b03930

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

M. Kim, H. Jung, A.C. Aragonès, I. Díez-Pérez, K.-H. Ahn, W.-J. Chung, D. Kim, S. Koo

Research output: Contribution to journal › Letter › peer-review

5 Citations (Scopus)

Abstract

textcopyright 2018 American Chemical Society. 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 G 0 , whose value was 47% that of the all-(E)-carotene ((3.23 × 10 -4 ) ± (1.23 × 10 -4 ) G 0 ).

Original language	English
Pages (from-to)	493–496
Journal	ORGANIC LETTERS
Volume	20
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.7b03930
Publication status	E-pub ahead of print - 10 Jan 2018

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title = "Role of Ring Ortho Substituents on the Configuration of Carotenoid Polyene Chains",

abstract = "textcopyright 2018 American Chemical Society. 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 G 0 , whose value was 47% that of the all-(E)-carotene ((3.23 × 10 -4 ) ± (1.23 × 10 -4 ) G 0 ).",

author = "M. Kim and H. Jung and A.C. Aragon{\`e}s and I. D{\'i}ez-P{\'e}rez and K.-H. Ahn and W.-J. Chung and D. Kim and S. Koo",

year = "2018",

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doi = "10.1021/acs.orglett.7b03930",

language = "English",

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journal = "ORGANIC LETTERS",

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TY - JOUR

T1 - Role of Ring Ortho Substituents on the Configuration of Carotenoid Polyene Chains

AU - Kim, M.

AU - Jung, H.

AU - Aragonès, A.C.

AU - Díez-Pérez, I.

AU - Ahn, K.-H.

AU - Chung, W.-J.

AU - Kim, D.

AU - Koo, S.

PY - 2018/1/10

Y1 - 2018/1/10

N2 - textcopyright 2018 American Chemical Society. 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 G 0 , whose value was 47% that of the all-(E)-carotene ((3.23 × 10 -4 ) ± (1.23 × 10 -4 ) G 0 ).

AB - textcopyright 2018 American Chemical Society. 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 G 0 , whose value was 47% that of the all-(E)-carotene ((3.23 × 10 -4 ) ± (1.23 × 10 -4 ) G 0 ).

U2 - 10.1021/acs.orglett.7b03930

DO - 10.1021/acs.orglett.7b03930

M3 - Letter

SN - 1523-7060

VL - 20

SP - 493

EP - 496

JO - ORGANIC LETTERS

JF - ORGANIC LETTERS

IS - 2

ER -

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

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