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Photocontrol of Polar Aromatic Interactions by a Bis‐Hemithioindigo Based Helical Receptor
Author(s) -
Guentner Manuel,
Uhl Edgar,
Mayer Peter,
Dube Henry
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604237
Subject(s) - photoisomerization , steric effects , chemistry , molecule , folding (dsp implementation) , structural isomer , polar , isomerization , helix (gastropod) , aromaticity , stereochemistry , crystallography , organic chemistry , catalysis , ecology , physics , astronomy , snail , electrical engineering , biology , engineering
The first example of a bis‐hemithioindigo (bis‐HTI)‐based molecular receptor was realized. Its folding and selective binding affinity for aromatic guest molecules can be precisely controlled by visible light and heat. The thermodynamically stable state of the bis‐HTI is the s‐shaped planar Z , Z ‐configuration. After irradiation with 420 nm light only the E , Z ‐configuration is formed in a highly selective photoisomerization. The E , Z ‐isomer adopts a helical conformation because of the implementation of repulsive steric interactions. The E , Z ‐configured helix is able to recognize electron‐poor aromatic guests exclusively through polar aromatic interactions and also distinguishes between regioisomers. After heating, the Z , Z ‐configuration is completely restored and the aromatic guest molecule is efficiently released.