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Fluorescent Amorphous Distyrylnaphthalene-Based Polymers: Synthesis, Characterization and Thin-Film Nanomolar Sensing of Nitroaromatics in Water

INQUISUR, Departamento de Química, Universidad Nacional del Sur (UNS)-CONICET, Av. Alem 1253, Bahía Blanca B8000CPB, Argentina
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Polymers 2018, 10(12), 1366; https://doi.org/10.3390/polym10121366
Received: 20 November 2018 / Revised: 5 December 2018 / Accepted: 6 December 2018 / Published: 10 December 2018
Two new fluorescent segmented conjugated polymers with either 1,4- or 2,6-distyrylnaphthalene chromophores and their model compounds were synthesized and the chemosensing abilities of the polymeric thin films to detect nitroaromatics (NACs) in aqueous media were evaluated. The structural, thermal and optical properties of the polymers were correlated with those displayed by their corresponding model compounds. Changes in the connectivity of naphthylene units caused minor differences in optical properties, morphology and quenching efficiencies. Molecular modeling highlighted the extremely bent character of polymer microstructures that explains their high solubility and amorphous character. Polymeric films are amorphous, strongly fluorescent and showed remarkable quenching efficiencies in the nanomolar range with picric acid (PA) and trinitrotoluene (TNT). Quenching experiments using either different nitroaromatic quenchers, excitation wavelengths, excitation beam path-lengths, or time of exposure of the film to the quenching solution evidenced the dominant role of inner filter effects (IFE) in the polymer response to NACs in the micromolar range. The sensing response towards PA, a quencher that strongly absorbs at the excitation wavelength, has an IFE contribution even at the nanomolar range, while the response towards the non-absorbing TNT depends only on the quenching occurring after diffusion of the analyte into the film. View Full-Text
Keywords: Segmented conjugated polymer; amorphous; thin films; fluorescent sensor; nitroaromatics; nanomolar detection Segmented conjugated polymer; amorphous; thin films; fluorescent sensor; nitroaromatics; nanomolar detection
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MDPI and ACS Style

Garay, R.O.; Schvval, A.B.; Almassio, M.F.; Del Rosso, P.G.; Romagnoli, M.J.; Montani, R.S. Fluorescent Amorphous Distyrylnaphthalene-Based Polymers: Synthesis, Characterization and Thin-Film Nanomolar Sensing of Nitroaromatics in Water. Polymers 2018, 10, 1366. https://doi.org/10.3390/polym10121366

AMA Style

Garay RO, Schvval AB, Almassio MF, Del Rosso PG, Romagnoli MJ, Montani RS. Fluorescent Amorphous Distyrylnaphthalene-Based Polymers: Synthesis, Characterization and Thin-Film Nanomolar Sensing of Nitroaromatics in Water. Polymers. 2018; 10(12):1366. https://doi.org/10.3390/polym10121366

Chicago/Turabian Style

Garay, Raúl O.; Schvval, Ana B.; Almassio, Marcela F.; Del Rosso, Pablo G.; Romagnoli, Maria J.; Montani, Rosana S. 2018. "Fluorescent Amorphous Distyrylnaphthalene-Based Polymers: Synthesis, Characterization and Thin-Film Nanomolar Sensing of Nitroaromatics in Water" Polymers 10, no. 12: 1366. https://doi.org/10.3390/polym10121366

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