Redox-induced conformational alteration of n,n-diarylamides.
We constructed a novel molecular conformational alteration system with an N-aryl-N-phenylacetamide structure, in which the N-aryl group consists of a hydroquinone-p-quinone system as a redox-dependent aromatic trigger. The amide conformation depended on the oxidation state of the aryl group, and the two states (compounds 2 and 3) were reversibly converted to each other by redox reactions. Such compounds would be applied as useful structural units for external stimulus-responsive control on the shape and function of large molecules or supramolecules.
Okamoto
Iwao
I
Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan. iokamoto@ac.jp
Yamasaki
Ryu
R
Sawamura
Mika
M
Kato
Takako
T
Nagayama
Naomi
N
Takeya
Tetsuya
T
Tamura
Osamu
O
Masu
Hyuma
H
Azumaya
Isao
I
Yamaguchi
Kentaro
K
Kagechika
Hiroyuki
H
Tanatani
Aya
A
D000577:Amides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D000577:Amides