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. 2013 Aug 12;19(33):10832-5.
doi: 10.1002/chem.201300984. Epub 2013 Jul 2.

Combined effect of polar substituents on the electronic flows in the carotenoid molecular wires

Yanan Zhao  1 , Stuart Lindsay, Sunhwa Jeon, Hyung-Jun Kim, Liang Su, Boram Lim, Sangho Koo
Affiliations

Combined effect of polar substituents on the electronic flows in the carotenoid molecular wires

Yanan Zhao et al. Chemistry. .
No abstract available

Keywords: carotenoids; conductance; electrochemistry; molecular electronics; molecular wire.

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Figures

Scheme 1
Scheme 1
a) Conceptual design of the circuit consisting of the carotenoid wires with polar substituents R1 and R2 as conductance modulators. b) Carotenoid molecular wires 1 and 2 with the aromatic substituent(s) × of different electronic nature.
Scheme 2
Scheme 2
Synthesis of the carotenoid molecular wires 1e–j (X ≠ Y) with the aromatic substituents of different electronic nature as the conductance (or resistance) elements.
Scheme 3
Scheme 3
Conductance measurement of the carotenoid wire 1c (X = Y = H in Scheme 2) by the repeated break-junction method. a) Making and breaking contacts between the STM probe and the carotenoid wires anchored to the gold substrate when the probe is pushed into and pulled away from the substrate. b) Control conductance curves over time and the control histogram. c) Steps in the sample conductance curves over time, which indicate the number of carotenoid molecules that make contacts to the STM probe and the histogram of the conductance value of the carotenoid wire (Gaussian fit to the conductance histogram is also shown above).
Scheme 4
Scheme 4
Control of the electronic flow in the carotenoid wire by the resistive substituent: a “bottle-neck” effect in the π-electron density by the electron-withdrawing substituent.
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