Covalent scrambling in porous polyarylthioethers through a stepwise SNAr for tunable bandgap and porosity.

Doyun Kim; Thien Si Nguyen; Hyejeong Lee; Bolormaa Bayarkhuu; Vepa Rozyyev; Jeehye Byun; Sheng Li; Cafer T. Yavuz

doi:10.1002/anie.202304378

Covalent scrambling in porous polyarylthioethers through a stepwise SNAr for tunable bandgap and porosity.

Doyun Kim, Thien Si Nguyen, Hyejeong Lee, Bolormaa Bayarkhuu, Vepa Rozyyev, Jeehye Byun, Sheng Li, Cafer T. Yavuz

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

4 Scopus citations

Abstract

Porous poly(aryl thioether)s offer stability and electronic tunability by robust sulfur-aryl conjugated architecture, but synthetic access is hindered due to limited control over the nucleophilic nature of sulfides and the air sensitivity of aromatic thiols. Here, we report a simple, one-pot, inexpensive, regioselective synthesis of highly porous poly(aryl thioether)s through polycondensation of perfluoroaromatic compounds with sodium sulfide. The unprecedented temperature-dependent para-directing formation of thioether linkages leads to a stepwise transition of the polymer extension into a network, thereby allowing fine control of the porosity and optical bandgaps. The obtained porous organic polymers with ultra-microporosity (

Original language	English (US)
Journal	Angewandte Chemie (International ed. in English)
DOIs	https://doi.org/10.1002/anie.202304378
State	Published - Apr 12 2023

Bibliographical note

KAUST Repository Item: Exported on 2023-04-14
Acknowledgements: This work was supported by the institutional program of KIST (2E32442), the National Research Foundation of Korea (NRF) Grant funded by the Korean government (MEST) (2021R1C1C1005774), and baseline funds from the King Abdullah University of Science and Technology (KAUST).

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.202304378

https://repository.kaust.edu.sa/bitstream/10754/691067/1/Angew%20Chem%20Int%20Ed%20-%202023%20-%20Kim%20-%20Covalent%20scrambling%20in%20porous%20polyarylthioethers%20through%20a%20stepwise%20SNAr%20for%20tunable_removed%20%281%29.pdf

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title = "Covalent scrambling in porous polyarylthioethers through a stepwise SNAr for tunable bandgap and porosity.",

abstract = "Porous poly(aryl thioether)s offer stability and electronic tunability by robust sulfur-aryl conjugated architecture, but synthetic access is hindered due to limited control over the nucleophilic nature of sulfides and the air sensitivity of aromatic thiols. Here, we report a simple, one-pot, inexpensive, regioselective synthesis of highly porous poly(aryl thioether)s through polycondensation of perfluoroaromatic compounds with sodium sulfide. The unprecedented temperature-dependent para-directing formation of thioether linkages leads to a stepwise transition of the polymer extension into a network, thereby allowing fine control of the porosity and optical bandgaps. The obtained porous organic polymers with ultra-microporosity (",

author = "Doyun Kim and Nguyen, {Thien Si} and Hyejeong Lee and Bolormaa Bayarkhuu and Vepa Rozyyev and Jeehye Byun and Sheng Li and Yavuz, {Cafer T.}",

note = "KAUST Repository Item: Exported on 2023-04-14 Acknowledgements: This work was supported by the institutional program of KIST (2E32442), the National Research Foundation of Korea (NRF) Grant funded by the Korean government (MEST) (2021R1C1C1005774), and baseline funds from the King Abdullah University of Science and Technology (KAUST).",

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doi = "10.1002/anie.202304378",

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AU - Kim, Doyun

AU - Nguyen, Thien Si

AU - Lee, Hyejeong

AU - Bayarkhuu, Bolormaa

AU - Rozyyev, Vepa

AU - Byun, Jeehye

AU - Li, Sheng

AU - Yavuz, Cafer T.

N1 - KAUST Repository Item: Exported on 2023-04-14 Acknowledgements: This work was supported by the institutional program of KIST (2E32442), the National Research Foundation of Korea (NRF) Grant funded by the Korean government (MEST) (2021R1C1C1005774), and baseline funds from the King Abdullah University of Science and Technology (KAUST).

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Y1 - 2023/4/12

N2 - Porous poly(aryl thioether)s offer stability and electronic tunability by robust sulfur-aryl conjugated architecture, but synthetic access is hindered due to limited control over the nucleophilic nature of sulfides and the air sensitivity of aromatic thiols. Here, we report a simple, one-pot, inexpensive, regioselective synthesis of highly porous poly(aryl thioether)s through polycondensation of perfluoroaromatic compounds with sodium sulfide. The unprecedented temperature-dependent para-directing formation of thioether linkages leads to a stepwise transition of the polymer extension into a network, thereby allowing fine control of the porosity and optical bandgaps. The obtained porous organic polymers with ultra-microporosity (

AB - Porous poly(aryl thioether)s offer stability and electronic tunability by robust sulfur-aryl conjugated architecture, but synthetic access is hindered due to limited control over the nucleophilic nature of sulfides and the air sensitivity of aromatic thiols. Here, we report a simple, one-pot, inexpensive, regioselective synthesis of highly porous poly(aryl thioether)s through polycondensation of perfluoroaromatic compounds with sodium sulfide. The unprecedented temperature-dependent para-directing formation of thioether linkages leads to a stepwise transition of the polymer extension into a network, thereby allowing fine control of the porosity and optical bandgaps. The obtained porous organic polymers with ultra-microporosity (

UR - http://hdl.handle.net/10754/691067

UR - https://onlinelibrary.wiley.com/doi/10.1002/anie.202304378

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DO - 10.1002/anie.202304378

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SN - 1433-7851

JO - Angewandte Chemie (International ed. in English)

JF - Angewandte Chemie (International ed. in English)

ER -

Covalent scrambling in porous polyarylthioethers through a stepwise SNAr for tunable bandgap and porosity.

Abstract

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