Pursuit of a rotary, light-driven molecular motor

ORGN 48

Thomas W. Bell, twb@unr.edu, Nicholas M. Hext, hext@unr.edu, HyunJong Kim, Esmaeel Masadeh, and Rolando Procupez. Department of Chemistry/216, University of Nevada, Reno, NV 89557-0020
A light-driven molecular motor of potential use in nanotechnology has been designed, based on "sterically geared" 9-(2,2,2-triphenylethylidene)fluorene (1). Several substituted analogs of 1,such as the 2-tert-butyl derivative, have been synthesized to investigate photoisomerization efficiency, which theoretically limits the efficiency of the target motor.  Quantum yields for photoisomerization of the 2-tert-butyl derivative at various wavelengths are significant, ranging from 4-9%, despite theoretical prediction of inefficient or negligible isomerization of the parent hydrocarbon, fulvene.  We have also synthesized several analogs with polar substituents, which increase absorption wavelengths and can greatly enhance photoisomerization quantum yields in this system.  The current status of our efforts to synthesize the target molecular motor, containing a chiral triarylmethane moiety, is also described.