Femtogram Detection of Explosive Nitroaromatics: Fluoranthene-Based Fluorescent Chemosensors

Herein we report a novel fluoranthene‐based fluorescent fluorophore 7,10‐bis(4‐bromophenyl)‐8,9‐bis[4‐(hexyloxy)phenyl]fluoranthene (S3) and its remarkable properties in applications of explosive detection. The sensitivity towards the detection of nitroaromatics (NACs) was evaluated through fluoresc...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-11, Vol.18 (46), p.14745-14751
Main Authors: Venkatramaiah, N., Kumar, Shiv, Patil, Satish
Format: Article
Language:English
Subjects:
Binding sites
Chemistry
explosives
femtochemistry
fluorescence
nitroaromatics
sensors
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Summary:Herein we report a novel fluoranthene‐based fluorescent fluorophore 7,10‐bis(4‐bromophenyl)‐8,9‐bis[4‐(hexyloxy)phenyl]fluoranthene (S3) and its remarkable properties in applications of explosive detection. The sensitivity towards the detection of nitroaromatics (NACs) was evaluated through fluorescence quenching in solution, vapor, and contact mode approaches. The contact mode approach using thin‐layer silica chromatograp‐ hic plates exhibited a femtogram (1.15 fg cm−2) detection limit for trinitrotoluene (TNT) and picric acid (PA), whereas the solution‐phase quenching showed PA detection at the 2–20 ppb level. Fluorescence lifetime measurements revealed that the quenching is static in nature and the quenching process is fully reversible. Binding energies between model binding sites of the S3 and analyte compounds reveal that analyte molecules enter into the cavity created by substituted phenyl rings of fluoranthene and are stabilized by strong intermolecular interactions with alkyl chains. It is anticipated that the sensor S3 could be a promising material for the construction of portable optical devices for the detection of onsite explosive nitroaromatics. Explosive discoveries: A novel fluoranthene‐based fluorescent fluorophore 7,10‐bis(4‐bromophenyl)‐8,9‐bis[4‐(hexyloxy)phenyl]fluoranthene (S3) and its remarkable properties in applications of explosive detection is reported (see figure). It is anticipated that sensor S3 could be a promising material in the construction of portable optical devices for onsite detection of explosive nitroaromatics.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201201764