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Role of Ring <i>Ortho</i> Substituents on the Configuration of Carotenoid Polyene Chains
Kim, Minsoo,Jung, Hyunuk,Aragonè,s, Albert C.,Dix301,ez-Pex301,rez, Ismael,Ahn, Kwang-Hyun,Chung, Wook-Jin,Kim, Dahye,Koo, Sangho American Chemical Society 2018 ORGANIC LETTERS Vol.20 No.2
<P>The 9-(<I>Z</I>)-configuration was exclusively obtained in the carotenoid polyene chain irrespective of olefination and disconnection methods for terminal <I>ortho</I>-unsubstituted benzene rings. The 2,6-dimethyl substituents in the terminal rings secure an all-(<I>E</I>)-polyene structure. The single molecular conductance of the pure 9-(<I>Z</I>)-carotene was measured for the first time to be 1.53 × 10<SUP>–4</SUP> ± 6.37 × 10<SUP>–5</SUP>G<SUB>0</SUB>, whose value was 47% that of the all-(<I>E</I>)-carotene ((3.23 × 10<SUP>–4</SUP>) ± (1.23 × 10<SUP>–4</SUP>) G<SUB>0</SUB>).</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2018/orlef7.2018.20.issue-2/acs.orglett.7b03930/production/images/medium/ol-2017-03930m_0006.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol7b03930'>ACS Electronic Supporting Info</A></P>