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Stereoselective Sensing by Substrate‐Controlled syn/anti Interconversion of a Stereodynamic Fluorosensor
Author(s) -
Tumambac Gilbert E.,
Mei Xuefeng,
Wolf Christian
Publication year - 2004
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.200400278
Subject(s) - chemistry , stereoselectivity , fluorescence , substrate (aquarium) , quantum yield , fluorescence spectroscopy , naphthalene , conformational isomerism , stereochemistry , yield (engineering) , photochemistry , molecule , organic chemistry , catalysis , physics , oceanography , quantum mechanics , geology , materials science , metallurgy
A stereoselective sensing method that is based on the unique stereodynamic and photochemical properties of 1,8‐diquinolylnaphthalenes has been developed. The ability to undergo substrate‐induced syn / anti interconversion and the striking difference in the fluorescence intensity of the syn and anti isomers of 1,8‐bis(2‐isopropyl‐4‐quinolyl)naphthalene ( 1 ) have been utilized for stereoselective sensing of the isomers of 1,2‐diaminocyclohexane ( 5 ). The conformational stability of 1 at room temperature greatly facilitated spectroscopic and crystallographic studies of this new prototype of stereodynamic fluorosensors. Fluorescence measurements of the anti and syn isomer of 1 revealed a quantum yield of 11.6% and 2%, respectively. NMR spectroscopy experiments confirmed that trans ‐ 5 stabilizes the C 2 ‐symmetric anti isomers of 1 , whereas cis‐ 5 favors formation of the less fluorescent meso syn ‐ 1 isomer, which results in a reduced fluorescence response. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)