Pentiptycene-Derived Fluorescence Turn-Off Polymer Chemosensor for Copper(II) Cation with High Selectivity and Sensitivity

Anting Chen; Wei Wu; Megan E A Fegley; Sherryllene S Pinnock; Jetty L Duffy-Matzner; William E Bernier; Wayne E Jones

doi:10.3390/polym9040118

Pentiptycene-Derived Fluorescence Turn-Off Polymer Chemosensor for Copper(II) Cation with High Selectivity and Sensitivity

Polymers (Basel). 2017 Mar 24;9(4):118. doi: 10.3390/polym9040118.

Authors

Anting Chen¹, Wei Wu², Megan E A Fegley³, Sherryllene S Pinnock⁴, Jetty L Duffy-Matzner⁵, William E Bernier⁶, Wayne E Jones⁷

Affiliations

¹ Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. achen47@binghamton.edu.
² Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. wwu39@binghamton.edu.
³ Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. mfegley@binghamton.edu.
⁴ Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. spinnoc1@binghamton.edu.
⁵ Department of Chemistry, Augustana University, Sioux Falls, SD 57197, USA. jetty.duffy@augie.edu.
⁶ Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. wbernier@binghamton.edu.
⁷ Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. wjones@binghamton.edu.

Abstract

Fluorescent conjugated polymers (FCPs) have been explored for selective detection of metal cations with ultra-sensitivity in environmental and biological systems. Herein, a new FCP sensor, tmeda-PPpETE (poly[(pentiptycene ethynylene)-alt-(thienylene ethynylene)] with a N,N,N'-trimethylethylenediamino receptor), has been designed and synthesized via Sonogashira cross-coupling reaction with the goal of improving solid state polymer sensor development. The polymer was found to be emissive at λ_max ~ 459 nm under UV radiation with a quantum yield of 0.119 at room temperature in THF solution. By incorporating diamino receptors and pentiptycene groups into the poly[(phenylene ethynylene)-(thiophene ethynylene)] (PPETE) backbone, the polymer showed an improved turn-off response towards copper(II) cation, with more than 99% quenching in fluorescence emission. It is capable of discriminating copper(II) cation from sixteen common cations, with a detection limit of 16.5 nM (1.04 ppb).

Keywords: chemical sensor; conjugated polymers; copper sensor; fluorescence; pentiptycene.

Abstract

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