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Sulfur- and Nitrogen-Containing Porous Donor–Acceptor Polymers as Real-Time Optical and Chemical Sensors

  • Yaroslav S. Kochergin
    Yaroslav S. Kochergin
    Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany
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  • , 
  • Yu Noda
    Yu Noda
    Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany
    More by Yu Noda
    Orcidhttp://orcid.org/0000-0003-0715-5534
  • , 
  • Ranjit Kulkarni
    Ranjit Kulkarni
    Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany
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  • , 
  • Klára Škodáková
    Klára Škodáková
    Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague, Czech Republic
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  • , 
  • Ján Tarábek
    Ján Tarábek
    Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague, Czech Republic
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    Orcidhttp://orcid.org/0000-0003-0116-3824
  • , 
  • Johannes Schmidt
    Johannes Schmidt
    Institute of Chemistry, Technische Universität Berlin, Hardenbergstraße 40, 10623 Berlin, Germany
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  • , and 
  • Michael J. Bojdys*
    Michael J. Bojdys
    Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany
    *E-mail: [email protected]
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    Orcidhttp://orcid.org/0000-0002-2592-4168
Cite this: Macromolecules 2019, 52, 20, 7696–7703
Publication Date (Web):October 4, 2019
https://doi.org/10.1021/acs.macromol.9b01643
Copyright © 2019 American Chemical Society
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    Abstract

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    Fully aromatic, organic polymers have the advantage of being composed from light, abundant elements, and are hailed as candidates in electronic and optical devices “beyond silicon”, yet, applications that make use of their π-conjugated backbone and optical bandgap are lacking outside of heterogeneous catalysis. Herein, we use a series of sulfur- and nitrogen-containing porous polymers (SNPs) as real-time optical and electronic sensors reversibly triggered and reset by acid and ammonia vapors. Our SNPs incorporate donor–acceptor and donor–donor motifs in extended networks and enable us to study the changes in bulk conductivity, optical bandgap, and fluorescence lifetimes as a function of π-electron de/localization in the pristine and protonated states. Interestingly, we find that protonated donor–acceptor polymers show a decrease of the optical bandgap by 0.42 to 0.76 eV and longer fluorescence lifetimes. In contrast, protonation of a donor–donor polymer does not affect its bandgap; however, it leads to an increase of electrical conductivity by up to 25-fold and shorter fluorescence lifetimes. The design strategies highlighted in this study open new avenues toward useful chemical switches and sensors based on modular purely organic materials.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.macromol.9b01643.

    • SNPs showing a rapid color change and marked red-shift of the absorption edge in solid-state UV–vis spectra (MP4)

    • Materials; characterization; synthetic protocols and procedures; overview of prepared materials; nitrogen gas adsorption/desorption analysis; thermogravimetric analysis (TGA); powder X-ray diffraction (PXRD); scanning electron microscopy (SEM); transmission electron microscopy (TEM); elemental analysis (EA); energy-dispersive X-ray (EDX) spectroscopy; X-ray photoelectron spectroscopy (XPS); solid-state UV–vis study and optical bandgap calculations; HCl vapor concentration study and polymer stability test; screening of different acids; Fourier-transform infrared spectroscopy (FTIR) study; complimentary stability study for SNPs (in addition to SNP-NDT1 cycling tests); solid state photoluminescence (PL); time-correlated single-photon counting (TCSPC) measurement; electronic conductivity measurements; electron paramagnetic resonance (EPR) study; additional temperature-dependent EPR study for SNP-NDT1 and SP-BTT networks; and additional references (PDF)

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