Jump to main content
Jump to site search

Issue 6, 2017
Previous Article Next Article

Extended cavity pyrene-based iptycenes for the turn-off fluorescence detection of RDX and common nitroaromatic explosives

Author affiliations

Abstract

Extended cavity pyrene-based iptycenes have been synthesized by using the Diels–Alder reaction between in situ generated dehydropyrenes and anthracene. The photophysical properties and the interaction of these iptycenes with nitro-explosive components were studied both in solution and in the solid state by using fluorescence spectroscopy and X-ray crystallography, respectively. Due to the presence of both the large iptycene cavity and the central pyrene core, an unprecedently high fluorescence-quenching response towards non-aromatic and non-planar 1,3,5-trinitroperhydro-1,3,5-triazine (RDX) has been observed both in solution (with an apparent Stern–Volmer constant value aKSV up to 1.53 × 103 M−1) and in the vapor phase (50–75% fluorescence quenching of the PU films doped with chemosensors). In the case of nitroaromatic explosives, nitrobenzene (NB), 2,4-DNT, TNT, and 2,4,6-trinitrophenol (TNP or picric acid, PA), pyrene-based iptycenes also demonstrate a good fluorescence-quenching response both in solutions (with apparent Stern–Volmer constant values aKSV = 0.4–8.0 × 103 M−1) and in the vapor phase (up to 90% fluorescence quenching of the PU films doped with chemosensors). The “sphere of action” fluorescence quenching model was suggested.

Graphical abstract: Extended cavity pyrene-based iptycenes for the turn-off fluorescence detection of RDX and common nitroaromatic explosives

Back to tab navigation

Supplementary files

Article information


Submitted
19 Sep 2016
Accepted
24 Jan 2017
First published
06 Feb 2017

New J. Chem., 2017,41, 2309-2320
Article type
Paper

Extended cavity pyrene-based iptycenes for the turn-off fluorescence detection of RDX and common nitroaromatic explosives

A. F. Khasanov, D. S. Kopchuk, I. S. Kovalev, O. S. Taniya, K. Giri, P. A. Slepukhin, S. Santra, M. Rahman, A. Majee, V. N. Charushin and O. N. Chupakhin, New J. Chem., 2017, 41, 2309
DOI: 10.1039/C6NJ02956F

Social activity

Search articles by author

Spotlight

Advertisements