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Electron-Rich Triphenylamine-Based Sensors for Picric Acid Detection

Chowdhury, Aniket and Mukherjee, Partha Sarathi (2015) Electron-Rich Triphenylamine-Based Sensors for Picric Acid Detection. In: JOURNAL OF ORGANIC CHEMISTRY, 80 (8). pp. 4064-4075.

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Official URL: http://dx.doi.org/10.1021/acs.joc.5b00348

Abstract

This paper demonstrates the role of solvent in selectivity and sensitivity of a series of electron-rich compounds for the detection of trace amounts of picric acid. Two new electron-rich fluorescent esters (6, 7) containing a triphenylamine backbone as well as their analogous carboxylic acids (8, 9) have been synthesized and characterized. Fluorescent triphenylamine coupled with an ethynyl moiety constitutes p-electron-rich selective and sensitive probes for electron-deficient picric acid (PA). In solution, the high sensitivity of all the sensors toward PA can be attributed to a combined effect of the ground-state charge-transfer complex formation and resonance energy transfer between the sensor and analyte. The acids 8 and 9 also showed enhanced sensitivity for nitroaromatics in the solid state, and their enhanced sensitivity could be attributed to exciton migration due to close proximity of the neighboring acid molecules, as evident from the X-ray diffraction study. The compounds were found to be quite sensitive for the detection of trace amount of nitroaromatics in solution, solid, and contact mode.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Keywords: AGGREGATION-INDUCED EMISSION; METAL-ORGANIC FRAMEWORK; SOLID-STATE; EXPLOSIVE NITROAROMATICS; FLUORESCENT CHEMOSENSORS; CONJUGATED POLYMERS; SELECTIVE DETECTION; FEMTOGRAM DETECTION; CHEMICAL SENSORS; TRACE
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 22 May 2015 07:31
Last Modified: 22 May 2015 07:31
URI: http://eprints.iisc.ac.in/id/eprint/51564

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