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Iptycene‐Based Fluorescent Sensors for Nitroaromatics and TNT
Author(s) -
Anzenbacher Pavel,
Mosca Lorenzo,
Palacios Manuel A.,
Zyryanov Grigory V.,
Koutnik Petr
Publication year - 2012
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.201200469
Subject(s) - dehydrohalogenation , vapours , fluorescence , stacking , materials science , polymer , cycloaddition , explosive material , molecule , quenching (fluorescence) , photochemistry , trinitrotoluene , picric acid , chemical engineering , chemistry , organic chemistry , optics , composite material , physics , neuroscience , biology , engineering , catalysis
Abstract Small‐molecule fluorescent sensors ( 1 – 5 ) for the recognition of nitroaromatic compounds, such as 2,4‐dinitrotoluene and the explosive TNT, were obtained by using a three‐step dehydrohalogenation cycloaddition protocol. The interaction of the receptors and nitroaromatics was studied both in solution and in the solid state by using fluorescence spectroscopy and X‐ray crystallography, respectively. It is shown that the iptycene receptors 1 – 5 provide a cavity suitable for binding nitroaromatic compounds in an edge‐to‐face mode, rather than simple ring‐stacking interactions. The results obtained inspired us to develop an inexpensive, reliable and robust sensor for vapour detection of explosives. Polymer nanofibres are particularly suitable for the production of such TNT sensors as they accelerate the mass exchange between the polymer and the vapours of TNT. Quenching of the sensors took place within 1 min compared to 10 min for a glass‐slide assay. Hence, the sensor performance can be improved by optimising the matrix material and morphology without resynthesising the sensor moieties.