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Photoswitchable π‐Extended Dithienylethenes with an Attached Molecular Recognition Site
Author(s) -
Bittner Iris,
Lüning Ulrich
Publication year - 2018
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.201800101
Subject(s) - photoswitch , chemistry , supramolecular chemistry , molecular switch , photochromism , stereochemistry , photochemistry , crystallography , molecule , crystal structure , organic chemistry
Photoswitchable dithienylethenes have been extended in positions 5 and 5′ with π‐systems resulting in absorptions of light with longer wavelengths when electrocyclization and ‐reversion are carried out. The extended π‐systems also improve conductivities potentially. cis ‐Orientation of the thienyl rings was accomplished by integrating the central double bond into maleic imides. The nitrogen atoms of the imides were substituted by a Hamilton receptor allowing supramolecular binding of complementary guests such as barbiturates. Both, a stiff and a flexible connection between photoswitch and receptor was realized. The resulting photoswitches showed reversible switching over several cycles and were able to bind diethyl barbiturate with binding constants of > 10 4 m –1 .