Unidirectional Rotary Motion in Isotopically Chiral Molecular Motors: A Computational Analysis.

Jun Wang,Bo Durbeej,Baswanth Oruganti

doi:10.1021/acs.orglett.0c02436

Jun Wang, Bo Durbeej + Show 1 more

Open Access

https://doi.org/10.1021/acs.orglett.0c02436

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Abstract

Molecular dynamics simulations are performed to explore if isotopic chirality can induce unidirectional rotary motion in molecular motors operated through double-bond photoisomerizations. Using a high-quantum yield motor featuring a chemically asymmetric carbon atom as reference, it is found that isotopically chiral counterparts of this motor sustain such motion almost equally well. Overall, the study reveals a previously unexplored role for isotopic chirality in the design of rotary molecular motors.

Highlights

Molecular dynamics simulations are performed to explore if isotopic chirality can induce unidirectional rotary motion in molecular motors operated through double-bond photoisomerizations
Double-bond photoisomerization is the reaction upon which many different types of synthetic molecular motors rely to produce 360° unidirectional rotary motion through the absorption of ultraviolet (UV) or visible light, with examples such as overcrowded-alkene,[1] hemithioindigo,[2] dibenzofulvene,[3] and N-alkyl-imine[4] motors
On the basis of quantum chemical calculations and non-adiabatic molecular dynamics (NAMD) simulations,[6] it has been demonstrated that the CW or CCW rotary direction of motors featuring Schiff-base and cyclohexenylidene motifs can be controlled by the intrinsic asymmetry of the ringpuckered cyclohexenylidene.[7]

Summary

Introduction

Molecular dynamics simulations are performed to explore if isotopic chirality can induce unidirectional rotary motion in molecular motors operated through double-bond photoisomerizations. Double-bond photoisomerization is the reaction upon which many different types of synthetic molecular motors rely to produce 360° unidirectional rotary motion through the absorption of ultraviolet (UV) or visible light, with examples such as overcrowded-alkene,[1] hemithioindigo,[2] dibenzofulvene,[3] and N-alkyl-imine[4] motors.

Results

Conclusion