Fluorene-based conjugated polymer with tethered thymines: click postpolymerization synthesis and optical response to mercury(II)

Authors

  • Yanli Lei,

    1. Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
    2. Key Laboratory of Functional Polymers, Xinjiang University, Urumqi 830046, People's Republic of China
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  • Fudong Ma,

    1. Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
    2. Key Laboratory of Functional Polymers, Xinjiang University, Urumqi 830046, People's Republic of China
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  • Yong Tian,

    1. Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
    2. Key Laboratory of Functional Polymers, Xinjiang University, Urumqi 830046, People's Republic of China
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  • Qiaoli Niu,

    1. Institute of Optoelectronic Materials and Technology, South China Normal University, Guangzhou 510631, People's Republic of China
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  • Hongyu Mi,

    1. Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
    2. Key Laboratory of Functional Polymers, Xinjiang University, Urumqi 830046, People's Republic of China
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  • Ismayil Nurulla,

    1. Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
    2. Key Laboratory of Functional Polymers, Xinjiang University, Urumqi 830046, People's Republic of China
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  • Wei Shi

    Corresponding author
    1. Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
    2. Key Laboratory of Functional Polymers, Xinjiang University, Urumqi 830046, People's Republic of China
    • Key Laboratory of Petroleum and Gas Fine Chemicals, Educational Ministry of China, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People's Republic of China
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Abstract

A kind of fluorene-based conjugated polymer with tethered thymine (T) groups {poly[(9,9-dioctyl)-2,7-fluorene-{9,9-dioctyl-4–1,2,3-triazol-[5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione}-2,7-fluorene]-co-[(9,9-dioctyl)-2,7-fluorene-4,7-bis(5-thiophen-2-yl)benzo-2,1,3-thiadiazole] (P-3)} was successfully synthesized by a Cu(I)-catalyzed click reaction between the acetylene-substituted polymer precursor {poly[(9,9-dioctyl)-2,7-fluorene-(9,9-dioctyl-4-phenylacetylene fluorene)]-co-[(9,9-dioctyl)-2,7-fluorene-4,7-bis(5-thiophen-2-yl)benzo-2,1,3-thiadiazole]} and 3′-azido-3′-deoxythymidine. The chemical structures of the intermediates and target polymer were verified by Fourier transform infrared spectroscopy and 1H-NMR analyses. The specific binding with Hg2+ of P-3 was corroborated by ultraviolet–visible spectroscopy and photoluminescence analyses against other metal ions. The results show that P-3 possessed selectivity and sensitivity toward Hg2+. Around 77% of photoluminescence intensity of P-3 was quenched when the concentration of Hg2+ reached 7.7 × 10−4 M and with a detection limit in the range of about 4.8 μM. A comparison experiment suggested that a synergic effect of the tethered T and S atoms interrelated with Hg2+ existed in P-3. Most of the fluorescence intensity of P-3 was recovered upon the addition of iodide anions to the P-3/Hg2+ complex; this suggested that P-3 could be used as a potential reversible optical Hg2+ probe. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

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