Isomeric sp2-C-conjugated porous organic polymer-mediated photo- and sono-catalytic detoxification of sulfur mustard simulant under ambient conditions

Ji Hyeon Kim; Hongryeol Yun; Dong Won Kang; Jinwoo Shin; Minjung Kang; Nem Singh; Ji Eun Jeong; Chang Seop Hong; Jong Seung Kim

doi:10.1016/j.matt.2021.10.005

Isomeric sp²-C-conjugated porous organic polymer-mediated photo- and sono-catalytic detoxification of sulfur mustard simulant under ambient conditions

Ji Hyeon Kim, Hongryeol Yun, Dong Won Kang, Jinwoo Shin, Minjung Kang, Nem Singh, Ji Eun Jeong, Chang Seop Hong, Jong Seung Kim

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

The development of efficient strategies for the sustainable detoxification of mustard gas simulants has longstanding demand for human safety. Here, we present for the first time a photo- and sono-catalyzed selective detoxification of mustard gas simulants under ambient conditions using conveniently prepared porous organic polymer (POP) catalysts. We developed a microwave-assisted synthesis of three isomeric tetraphenylethylene-based POPs (TP_o, TP_m, and TP_p) bearing fully sp²-hybridized carbon frameworks. Among the three isomers, TP_m efficiently generated ¹O₂, whereas TP_p generated both O₂^.– and HO. under visible light irradiation, both TP_m and TP_p efficiently generated ROS to selectively convert 2-chloroethyl ethyl sulfide (CEES) into nontoxic 2-chloroethyl ethyl sulfoxide (CEESO) in the atmospheric conditions, through a known conversion mechanism. TP_m and TP_p can also generate ¹O₂ under ultrasound irradiation. This work provides insight into designing new POP photo- and sono-catalysts to generate ROS in widespread applications.

Original language	English
Pages (from-to)	3774-3785
Number of pages	12
Journal	Matter
Volume	4
Issue number	11
DOIs	https://doi.org/10.1016/j.matt.2021.10.005
Publication status	Published - 2021 Nov 3

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea ( NRF-2021R1A2B5B03086313 , 2021M3I3A1084573 , to C.S.H.), the Priority Research Centers Program ( 2019R1A6A1A11044070 , to C.S.H.), CRI project ( 2018R1A3B1052702 , NRF-2019M3E5D1A01068998 , to J.S.K .), the Global PhD Fellowship (GPF) program (2019H1A2A1074096, J.H.K.) from the National Research Foundation of Korea (NRF) funded by the Ministry of Education . We are grateful to Prof. Kwangyeol Lee for the TEM measurements. We thank the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics (IBS-R023-D1) for providing NMR spectrometry and professional technical support.

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF-2021R1A2B5B03086313, 2021M3I3A1084573, to C.S.H.), the Priority Research Centers Program (2019R1A6A1A11044070, to C.S.H.), CRI project (2018R1A3B1052702, NRF-2019M3E5D1A01068998, to J.S.K.), the Global PhD Fellowship (GPF) program (2019H1A2A1074096, J.H.K.) from the National Research Foundation of Korea (NRF) funded by the Ministry of Education. We are grateful to Prof. Kwangyeol Lee for the TEM measurements. We thank the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics (IBS-R023-D1) for providing NMR spectrometry and professional technical support. J.H.K. H.Y. and D.W.K. contributed to synthesis, characterization, solution experiments, and NMR studies. J.S. and M.K. contributed to the figure arrangement. N.S. contributed to manuscript grammatical editing. J.-E.J. performed PLQY analyses. J.H.K. H.Y. D.W.K. N.S. C.S.H. and J.S.K. contributed to the writing, review, and editing of the manuscript. J.H.K. C.S.H. and J.S.K. received study-enabling funding. D.W.K. contributed to the initial project conception. C.S.H. and J.S.K. contributed to supervision and project development. All authors proofread, commented on, and approved the final version of the manuscript. The authors declare no competing interests.

Publisher Copyright:
© 2021 Elsevier Inc.

Keywords

MAP4: Demonstrate
ambient condition
chemical warfare agent
photocatalyst
porous organic polymer
reactive oxygen species
sonocatalyst
sulfur mustard simulant
sulfur oxidation
ultrasound

ASJC Scopus subject areas

General Materials Science

Access to Document

10.1016/j.matt.2021.10.005

Cite this

@article{d7d6f04860b748288963e7aea080def3,

title = "Isomeric sp2-C-conjugated porous organic polymer-mediated photo- and sono-catalytic detoxification of sulfur mustard simulant under ambient conditions",

abstract = "The development of efficient strategies for the sustainable detoxification of mustard gas simulants has longstanding demand for human safety. Here, we present for the first time a photo- and sono-catalyzed selective detoxification of mustard gas simulants under ambient conditions using conveniently prepared porous organic polymer (POP) catalysts. We developed a microwave-assisted synthesis of three isomeric tetraphenylethylene-based POPs (TPo, TPm, and TPp) bearing fully sp2-hybridized carbon frameworks. Among the three isomers, TPm efficiently generated 1O2, whereas TPp generated both O2.– and HO. under visible light irradiation, both TPm and TPp efficiently generated ROS to selectively convert 2-chloroethyl ethyl sulfide (CEES) into nontoxic 2-chloroethyl ethyl sulfoxide (CEESO) in the atmospheric conditions, through a known conversion mechanism. TPm and TPp can also generate 1O2 under ultrasound irradiation. This work provides insight into designing new POP photo- and sono-catalysts to generate ROS in widespread applications.",

keywords = "MAP4: Demonstrate, ambient condition, chemical warfare agent, photocatalyst, porous organic polymer, reactive oxygen species, sonocatalyst, sulfur mustard simulant, sulfur oxidation, ultrasound",

author = "Kim, {Ji Hyeon} and Hongryeol Yun and Kang, {Dong Won} and Jinwoo Shin and Minjung Kang and Nem Singh and Jeong, {Ji Eun} and Hong, {Chang Seop} and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea ( NRF-2021R1A2B5B03086313 , 2021M3I3A1084573 , to C.S.H.), the Priority Research Centers Program ( 2019R1A6A1A11044070 , to C.S.H.), CRI project ( 2018R1A3B1052702 , NRF-2019M3E5D1A01068998 , to J.S.K .), the Global PhD Fellowship (GPF) program (2019H1A2A1074096, J.H.K.) from the National Research Foundation of Korea (NRF) funded by the Ministry of Education . We are grateful to Prof. Kwangyeol Lee for the TEM measurements. We thank the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics (IBS-R023-D1) for providing NMR spectrometry and professional technical support. Funding Information: This work was supported by the National Research Foundation of Korea (NRF-2021R1A2B5B03086313, 2021M3I3A1084573, to C.S.H.), the Priority Research Centers Program (2019R1A6A1A11044070, to C.S.H.), CRI project (2018R1A3B1052702, NRF-2019M3E5D1A01068998, to J.S.K.), the Global PhD Fellowship (GPF) program (2019H1A2A1074096, J.H.K.) from the National Research Foundation of Korea (NRF) funded by the Ministry of Education. We are grateful to Prof. Kwangyeol Lee for the TEM measurements. We thank the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics (IBS-R023-D1) for providing NMR spectrometry and professional technical support. J.H.K. H.Y. and D.W.K. contributed to synthesis, characterization, solution experiments, and NMR studies. J.S. and M.K. contributed to the figure arrangement. N.S. contributed to manuscript grammatical editing. J.-E.J. performed PLQY analyses. J.H.K. H.Y. D.W.K. N.S. C.S.H. and J.S.K. contributed to the writing, review, and editing of the manuscript. J.H.K. C.S.H. and J.S.K. received study-enabling funding. D.W.K. contributed to the initial project conception. C.S.H. and J.S.K. contributed to supervision and project development. All authors proofread, commented on, and approved the final version of the manuscript. The authors declare no competing interests. Publisher Copyright: {\textcopyright} 2021 Elsevier Inc.",

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T1 - Isomeric sp2-C-conjugated porous organic polymer-mediated photo- and sono-catalytic detoxification of sulfur mustard simulant under ambient conditions

AU - Kim, Ji Hyeon

AU - Yun, Hongryeol

AU - Kang, Dong Won

AU - Shin, Jinwoo

AU - Kang, Minjung

AU - Singh, Nem

AU - Jeong, Ji Eun

AU - Hong, Chang Seop

AU - Kim, Jong Seung

N1 - Funding Information: This work was supported by the National Research Foundation of Korea ( NRF-2021R1A2B5B03086313 , 2021M3I3A1084573 , to C.S.H.), the Priority Research Centers Program ( 2019R1A6A1A11044070 , to C.S.H.), CRI project ( 2018R1A3B1052702 , NRF-2019M3E5D1A01068998 , to J.S.K .), the Global PhD Fellowship (GPF) program (2019H1A2A1074096, J.H.K.) from the National Research Foundation of Korea (NRF) funded by the Ministry of Education . We are grateful to Prof. Kwangyeol Lee for the TEM measurements. We thank the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics (IBS-R023-D1) for providing NMR spectrometry and professional technical support. Funding Information: This work was supported by the National Research Foundation of Korea (NRF-2021R1A2B5B03086313, 2021M3I3A1084573, to C.S.H.), the Priority Research Centers Program (2019R1A6A1A11044070, to C.S.H.), CRI project (2018R1A3B1052702, NRF-2019M3E5D1A01068998, to J.S.K.), the Global PhD Fellowship (GPF) program (2019H1A2A1074096, J.H.K.) from the National Research Foundation of Korea (NRF) funded by the Ministry of Education. We are grateful to Prof. Kwangyeol Lee for the TEM measurements. We thank the Institute for Basic Science (IBS) Center for Molecular Spectroscopy and Dynamics (IBS-R023-D1) for providing NMR spectrometry and professional technical support. J.H.K. H.Y. and D.W.K. contributed to synthesis, characterization, solution experiments, and NMR studies. J.S. and M.K. contributed to the figure arrangement. N.S. contributed to manuscript grammatical editing. J.-E.J. performed PLQY analyses. J.H.K. H.Y. D.W.K. N.S. C.S.H. and J.S.K. contributed to the writing, review, and editing of the manuscript. J.H.K. C.S.H. and J.S.K. received study-enabling funding. D.W.K. contributed to the initial project conception. C.S.H. and J.S.K. contributed to supervision and project development. All authors proofread, commented on, and approved the final version of the manuscript. The authors declare no competing interests. Publisher Copyright: © 2021 Elsevier Inc.

PY - 2021/11/3

Y1 - 2021/11/3

N2 - The development of efficient strategies for the sustainable detoxification of mustard gas simulants has longstanding demand for human safety. Here, we present for the first time a photo- and sono-catalyzed selective detoxification of mustard gas simulants under ambient conditions using conveniently prepared porous organic polymer (POP) catalysts. We developed a microwave-assisted synthesis of three isomeric tetraphenylethylene-based POPs (TPo, TPm, and TPp) bearing fully sp2-hybridized carbon frameworks. Among the three isomers, TPm efficiently generated 1O2, whereas TPp generated both O2.– and HO. under visible light irradiation, both TPm and TPp efficiently generated ROS to selectively convert 2-chloroethyl ethyl sulfide (CEES) into nontoxic 2-chloroethyl ethyl sulfoxide (CEESO) in the atmospheric conditions, through a known conversion mechanism. TPm and TPp can also generate 1O2 under ultrasound irradiation. This work provides insight into designing new POP photo- and sono-catalysts to generate ROS in widespread applications.

AB - The development of efficient strategies for the sustainable detoxification of mustard gas simulants has longstanding demand for human safety. Here, we present for the first time a photo- and sono-catalyzed selective detoxification of mustard gas simulants under ambient conditions using conveniently prepared porous organic polymer (POP) catalysts. We developed a microwave-assisted synthesis of three isomeric tetraphenylethylene-based POPs (TPo, TPm, and TPp) bearing fully sp2-hybridized carbon frameworks. Among the three isomers, TPm efficiently generated 1O2, whereas TPp generated both O2.– and HO. under visible light irradiation, both TPm and TPp efficiently generated ROS to selectively convert 2-chloroethyl ethyl sulfide (CEES) into nontoxic 2-chloroethyl ethyl sulfoxide (CEESO) in the atmospheric conditions, through a known conversion mechanism. TPm and TPp can also generate 1O2 under ultrasound irradiation. This work provides insight into designing new POP photo- and sono-catalysts to generate ROS in widespread applications.

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KW - chemical warfare agent

KW - photocatalyst

KW - porous organic polymer

KW - reactive oxygen species

KW - sonocatalyst

KW - sulfur mustard simulant

KW - sulfur oxidation

KW - ultrasound

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