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Post-Synthetically Elaborated BODIPY-Based Porous Organic Polymers (POPs) for the Photochemical Detoxification of a Sulfur Mustard Simulant
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    Post-Synthetically Elaborated BODIPY-Based Porous Organic Polymers (POPs) for the Photochemical Detoxification of a Sulfur Mustard Simulant
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    • Ahmet Atilgan
      Ahmet Atilgan
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
    • M. Mustafa Cetin
      M. Mustafa Cetin
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
      Department of Bioinformatics and Genetics, Faculty of Engineering and Natural Science, Kadir Has University, 34083 Cibali Campus Fatih, Istanbul, Turkey
    • Jierui Yu
      Jierui Yu
      Department of Chemistry and Biochemistry, Southern Illinois University, 1245 Lincoln Drive, Carbondale, Illinois 62901, United States
      More by Jierui Yu
    • Yassine Beldjoudi
      Yassine Beldjoudi
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
    • Jian Liu
      Jian Liu
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
      More by Jian Liu
    • Charlotte L. Stern
      Charlotte L. Stern
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
    • Furkan M. Cetin
      Furkan M. Cetin
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
    • Timur Islamoglu
      Timur Islamoglu
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
    • Omar K. Farha
      Omar K. Farha
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
    • Pravas Deria*
      Pravas Deria
      Department of Chemistry and Biochemistry, Southern Illinois University, 1245 Lincoln Drive, Carbondale, Illinois 62901, United States
      *[email protected]
      More by Pravas Deria
    • J. Fraser Stoddart*
      J. Fraser Stoddart
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
      Institute of Molecular Design and Synthesis, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. China
      School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia
      *[email protected]
    • Joseph T. Hupp*
      Joseph T. Hupp
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States
      *[email protected]
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 43, 18554–18564
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    https://doi.org/10.1021/jacs.0c07784
    Published September 26, 2020
    Copyright © 2020 American Chemical Society

    Abstract

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    Designing new materials for the effective detoxification of chemical warfare agents (CWAs) is of current interest given the recent use of CWAs. Although halogenated boron-dipyrromethene derivatives (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene or BDP or BODIPY) at the 2 and 6 positions have been extensively explored as efficient photosensitizers for generating singlet oxygen (1O2) in homogeneous media, their utilization in the design of porous organic polymers (POPs) has remained elusive due to the difficulty of controlling polymerization processes through cross-coupling synthesis pathways. Our approach to overcome these difficulties and prepare halogenated BODIPY-based porous organic polymers (X-BDP-POP where X = Br or I) represents an attractive alternative through post-synthesis modification (PSM) of the parent hydrogenated polymer. Upon synthesis of both the parent polymer, H-BDP-POP, and its post-synthetically modified derivatives, Br-BDP-POP and I-BDP-POP, the BET surface areas of all POPs have been measured and found to be 640, 430, and 400 m2·g–1, respectively. In addition, the insertion of heavy halogen atoms at the 2 and 6 positions of the BODIPY unit leads to the quenching of fluorescence (both polymer and solution-phase monomer forms) and the enhancement of phosphorescence (particularly for the iodo versions of the polymers and monomers), as a result of efficient intersystem crossing. The heterogeneous photocatalytic activities of both the parent POP and its derivatives for the detoxification of the sulfur mustard simulant, 2-chloroethyl ethyl sulfide (CEES), have been examined; the results show a significant enhancement in the generation of singlet oxygen (1O2). Both the bromination and iodination of H-BDP-POP served to shorten by 5-fold of the time needed for the selective and catalytic photo-oxidation of CEES to 2-chloroethyl ethyl sulfoxide (CEESO).

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    • Materials/general methods/instrumentation, synthesis protocols, NMR spectroscopy, crystallographic characterization, N2 adsorption, desorption isotherms, photophysical characterization, diffuse reflectance for infrared Fourier transform spectroscopy, powder X-ray diffraction, thermogravimetric analysis, X-ray photoelectron spectroscopy, density functional theory calculations, and photocatalytic studies (PDF)

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