Photomodulated chiral induction in helical azobenzene oligomers.
Appending L-alanine to the terminal positions of a helical azobenzene oligomer produced a P helical bias, which increased with oligomer length. Irradiation gave rise to E-->Z isomerization of the terminal azo linkages, which displaced the stereogenic center of L-Ala from the helix backbone and suppressed chiral induction. Theoretical simulations of the CD spectrum of the P helical conformation are in qualitative agreement with the experimental spectra.
King
Eric D
ED
Department of Chemistry, The Ohio State University, Columbus, OH 43210, USA.
Tao
Peng
P
Sanan
Toby T
TT
Hadad
Christopher M
CM
Parquette
Jon R
JR
D000409:Alanine / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D002942:Circular Dichroism; D003198:Computer Simulation; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
D001391:Azo Compounds; D011108:Polymers; C009850:azobenzene; D000409:Alanine