title: Charge-Transfer-Induced Fluorescence Quenching of Anthracene Derivatives and Selective Detection of Picric Acid.
abstract: 2,6-Divinylpyridine-appended anthracene derivatives flanked by two alkyl chains at the 9,10-position of the core have been designed, synthesized, and characterized by NMR, MALDI-TOF, FTIR, and single-crystal XRD. These anthracene derivatives are able to recognize picric acid (2,4,6-trinitrophenol, PA) selectively down to parts per billion (ppb) level in aqueous as well as nonaqueous medium. Fluorescence emission of these derivatives in solution is significantly quenched by adding trace amounts of PA, even in the presence of other competing analogues, such as 2,4-dinitrophenol (2,4-DNP), 4-nitrophenol (NP), nitrobenzene (NB), benzoic acid (BA), and phenol (PH). The high sensitivity of these derivatives toward PA is considered as a combined effect of the proton-induced intramolecular charge transfer (ICT) as well as electron transfer from the electron-rich anthracene to the electron-deficient PA. Moreover, visual detection of PA has been successfully demonstrated in the solid state by using different substrates.
authors.affiliation: Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032, India.
authors.forename: Dines Chandra
authors.initials: DC
authors.lastname: Santra
authors.affiliation: Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032, India.
authors.forename: Manas Kumar
authors.initials: MK
authors.lastname: Bera
authors.affiliation: Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032, India.
authors.forename: Pradip Kumar
authors.initials: PK
authors.lastname: Sukul
authors.affiliation: Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032, India. psusm2@iacs.res.in.
authors.forename: Sudip
authors.identifier: http://orcid.org/0000-0001-5358-5653
authors.initials: S
authors.lastname: Malik
keywords: fluorescence; nitro-aromatic explosives; ppb level detection; sensors; vinylpyridine