A Rotary Molecular Motor Gated by Electrical Energy

DFT calculations predict that the chiral pentiptycene derivative E-1 possesses distinct rotational potential energy surfaces in the neutral vs the radical anionic (E-1 •–) form such that continued electrochemical switching between E-1 and E-1 •– could lead to a directional rotation of the pentiptyce...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 23; pp. 6100 - 6103
Main Authors Kao, Chen-Yi, Lu, Hsiu-Feng, Chao, Ito, Yang, Jye-Shane
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.12.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MACHINES
MOTION
DRIVEN
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Summary:DFT calculations predict that the chiral pentiptycene derivative E-1 possesses distinct rotational potential energy surfaces in the neutral vs the radical anionic (E-1 •–) form such that continued electrochemical switching between E-1 and E-1 •– could lead to a directional rotation of the pentiptycene rotor about the exocyclic C–C bond. The time scale of random Brownian rotation is ∼106 s for E-1 and ∼170 s for E-1 •– at 150 K, and thus a switching time scale of 0.2 s could readily bias the rotation direction to >99% at 150 K. The synthetic feasibility, line-shape analysis on the VT 1H NMR spectra, and electrochemical redox switching of E-1 are demonstrated.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502946v