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 suppr...

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Bibliographic Details
Published in:Organic letters 2008-05, Vol.10 (9), p.1671-1674
Main Authors: King, Eric D, Tao, Peng, Sanan, Toby T, Hadad, Christopher M, Parquette, Jon R
Format: Article
Language:English
Subjects:
Alanine - chemistry
Azo Compounds - chemistry
Circular Dichroism
Computer Simulation
Models, Molecular
Molecular Conformation
Molecular Structure
Polymers - chemistry
Stereoisomerism
Thermodynamics
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8004722