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Systematic Modulation of Hydrogen Bond Donors in Aminoazobenzene Derivatives Provides Further Evidence for the Concerted Inversion Photoisomerization Pathway
Author(s) -
Bandara H. M. Dhammika,
Basa Prem N.,
Yan Jingjing,
Camire Casey E.,
MacDonald John C.,
Jackson Randy K.,
Burdette Shawn C.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300525
Subject(s) - chemistry , photoisomerization , intramolecular force , isomerization , hydrogen bond , photochemistry , pyridine , aniline , stereochemistry , molecule , catalysis , medicinal chemistry , organic chemistry
A series of aminoazobenzene derivatives structurally related to AzoAMP‐1 have been prepared and characterized by using a variety of analytical techniques. AzoAMP‐1 is based on 2,2′‐diaminoazobenzene with N ‐methylpyridine groups. The new derivatives all contain a hydrogen bond between the aniline hydrogen atom and the azo group, as well as a separate pendant functional group that could contribute an additional hydrogen‐bond acceptor to an intramolecular network. A combination of photoisomerization studies and NMR spectroscopic and X‐ray crystallographic investigations suggest that AzoAMP‐1 possesses a unique structure that prevents isomerization through the concerted inversion pathway, which cannot be reproduced with other types or arrangements of substituents. Only AzoAMQ, which contains a similar quinolone heterocycle in place of the pyridine group of AzoAMP‐1, displayed somewhat similar photochemistry.