A Rotary Molecular Motor Gated by Electrical Energy
Journal
Organic Letters
Journal Volume
16
Journal Issue
23
Pages
6100-6103
Date Issued
2014
Author(s)
Abstract
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 ∼10(6) 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 (1)H NMR spectra, and electrochemical redox switching of E-1 are demonstrated.
SDGs
Type
journal article