Title
Chiral Recognition of Azo-Schiff Base Ligands, Their Cu(II) Complexes, and Their Docking to Laccase as Mediators
Abstract
Chiral crystals were discovered due to spontaneous resolution when enantiomers of 4-phenyldiazenyl-2-[(R or S)-(1-phenylethyl)-iminomethyl]phenol and its racemic mixture were prepared. Using two ligands per molecule, optically active R,R and S,S enantiomers and meso R,S diastereomer of Cu(II) complexes were prepared. Strong chiral recognition was expected for them. Laccase has attracted attention as a catalyst that reduces oxygen to water in a cathode of biofuel cells, which can be effectively mediated by metal complexes. Furthermore, azobenzene can align perpendicularly to the polarization direction of irradiating linearly polarized ultraviolet light (Weigert effect) as well as to the conventional cis-trans photoisomerization accompanying the shift of redox potential. Thus, we also studied the photo-induced control of cis-trans forms and the alignment of these Cu(II) complexes as a mediator to fit laccase appropriately. We discuss photo-induced control on not only electronically but also sterically-favored redox conditions. The meso(R,S)-form of the Cu(II) complex in cis-form was found to be the best at increasing the current of cyclic voltammetry (CV) among the three R,R and S,S enantiomers and the R,S diastereomer of the Cu(II) complexes.
Year
DOI
Venue
2019
10.3390/sym11050666
SYMMETRY-BASEL
Keywords
Field
DocType
chiral Schiff base,spontaneous resolution,enantiomer,diastereomer,azobenzene,Weigert effect,copper(II) (Cu(II)) complex,laccase
Chirality (chemistry),Photoisomerization,Schiff base,Mathematical analysis,Polymer chemistry,Diastereomer,Azobenzene,Enantiomer,Mathematics,Ultraviolet light,Racemic mixture
Journal
Volume
Issue
Citations 
11
5.0
0
PageRank 
References 
Authors
0.34
0
6
Name
Order
Citations
PageRank
Fuki Kunitake100.34
Jong-Yeon Kim200.34
Shiomi Yagi300.68
Shu Yamzaki400.34
Tomoyuki Haraguchi511.98
Takashiro Akitsu612.32