Volume 81, Issue 12 p. 1360-1370
Full Paper

Vinylanthracene-Based Compounds as Electron-Rich Sensors for Explosives Recognition

Aniket Chowdhury

Aniket Chowdhury

Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, Karnataka, 560012 India

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Prof. Dr. Partha Sarathi Mukherjee

Corresponding Author

Prof. Dr. Partha Sarathi Mukherjee

Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, Karnataka, 560012 India

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First published: 12 September 2016
Citations: 10

Graphical Abstract

Sensing with a twist: Four new vinylanthracene-based organic luminescent compounds have been prepared. The twisted aromatic backbone imparted strong luminescence in the solution and solid states, which was used for the detection of explosives, especially picric acid (PA) and other nitroaromatic compounds (NACs), through a combination of resonance energy transfer and photo-induced electron transfer processes (see figure).

Abstract

Four new vinylanthracene-based fluorescent molecules were synthesized and characterized. The highly fluorescent vinylanthracene moiety was coupled with the ethynylbenzene group to yield rigid and electron-rich π systems, which were utilized as selective and sensitive probes for picric acid in both the solution and solid states. In solution, the molecules demonstrated signal amplification by a combined effect of photo-induced electron transfer and resonance energy transfer, whereas in the solid state the enhanced sensitivity was attributed to a collective effect of PET and exciton migration among closely spaced molecules. In direct contact mode experiments, thin films of the molecules demonstrated discernible changes in fluorescent intensity, which shows that the molecules are potential materials for in-the-field applications.