Conjugated polymers for the fluorescent detection of nitroaromatics: Influence of side‐chain sterics and π‐system electronics |
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| Authors: | Tyler L. Duniho Brynna J. Laughlin Ashley A. Buelt William F. Baker Catherine A. Conrad Rhett C. Smith |
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| Affiliation: | 1. Department of Chemistry, Clemson University, , Clemson, South Carolina, 29634;2. Laboratory for Creative Inquiry in Chemistry, Clemson University, , Clemson, South Carolina, 29634;3. Center for Optical Materials Science and Engineering Technologies, , Anderson, South Carolina, 29625 |
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| Abstract: | A series of eight poly(p‐phenylene vinylene) (PPV) and poly(p‐phenylene ethynylene) (PPE) ( P1–P8 ) derivatives were tested for their ability to detect the nitroaromatic explosive 2,4,6‐trinitrotoluene (TNT) and its model compound 2,6‐dinitrotoluene (DNT). The polymers P1–P8 represent five structural classes that have not been examined for nitroaromatic sensing. These new motifs include PPE derivatives with a main‐chain m‐terphenyl unit ( P1 ) or oxacyclophane canopy‐like structure ( P2 ) and PPV derivatives with 2,6‐mesitylenephenylene repeats ( P3 and P4 ), 9,9‐dialkyl‐1,4‐fluorenylene repeats ( P5 and P6 ), or m‐phenylene units that periodically disrupt π‐conjugation along the backbone of the polymer ( P7 and P8 ). The time‐dependent photoluminescent response of films to TNT and DNT and the solution‐phase Stern‐Volmer quenching constants for both TNT and DNT were determined. The results are rationalized in terms of side‐chain sterics and π‐system electronics and are discussed relative to known conjugated polymers. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 1487–1492 |
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| Keywords: | conjugated polymers explosives fluorescence fluorescent sensing nitroaromatic sensors TNT |
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