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Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation

Manying Liu, Pan Liu, Zikang Lei, Rongjuan Ba, Suxiang Ge, Jiachang Li, Huimin Jia, Yuanting Qiao Orcid Logo, Yange Zhang, Zhi Zheng

ACS Applied Polymer Materials, Volume: 6, Issue: 22, Pages: 13805 - 13812

Swansea University Author: Yuanting Qiao Orcid Logo

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DOI (Published version): 10.1021/acsapm.4c02663

Abstract

Although hyper-cross-linked polymers (HCPs) offer significant advantages, their industrial scalability has been impeded by concerns regarding waste generation. To mitigate this challenge, we have successfully developed an efficient and cost-effective green synthesis method for phenanthrenequinone-ba...

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Published in: ACS Applied Polymer Materials
ISSN: 2637-6105 2637-6105
Published: American Chemical Society (ACS) 2024
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URI: https://cronfa.swan.ac.uk/Record/cronfa68450
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spelling 2025-02-04T14:50:36.9437158 v2 68450 2024-12-03 Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation ceae57100ecb7c4b2883e29079a8985d 0000-0002-7741-9278 Yuanting Qiao Yuanting Qiao true false 2024-12-03 EAAS Although hyper-cross-linked polymers (HCPs) offer significant advantages, their industrial scalability has been impeded by concerns regarding waste generation. To mitigate this challenge, we have successfully developed an efficient and cost-effective green synthesis method for phenanthrenequinone-based HCPs (PQ-HCPs). This method employs a Friedel–Crafts alkylation reaction, utilizing trifluoromethanesulfonic acid as a catalyst and PQ as the starting material. Under low catalyst concentrations, electrophilic sulfonation reactions are predominant. However, increasing the catalyst to a 2 equiv amount significantly shifts the reaction pathway toward Friedel–Crafts alkylation cross-linking. The resultant optimal sample, PQ-HCP-1:3, boasts an impressive specific surface area of up to 428 m2·g–1. Dye adsorption experiments on these samples demonstrated a marked selective affinity for Rhodamine B, with the hydrophilicity of the samples being a pivotal factor in the adsorption process. This innovative approach substantially outperforms traditional methods, which typically involve ferric chloride (FeCl3) and aluminum chloride (AlCl3), by significantly reducing the production of solid waste and effluent during the chemical reaction process. Journal Article ACS Applied Polymer Materials 6 22 13805 13812 American Chemical Society (ACS) 2637-6105 2637-6105 Hyper-cross-linked polymer, green synthesis, solid waste, phenanthrenequinone, trifluoromethanesulfonic acid 22 11 2024 2024-11-22 10.1021/acsapm.4c02663 COLLEGE NANME Engineering and Applied Sciences School COLLEGE CODE EAAS Swansea University Not Required This work was financially supported by the National NaturalScience Foundation of China (Grants 52072327, 62274141,and 22276160), Higher Education and Teaching ReformationProject (2024SJGLX0451), Academic Degrees & GraduateEducation Reform Project of Henan Province (YJS2022JD34),Key Research and Development Projects of Universities inHenan Province (23B430009), and Natural Science Founda-tion of Henan Province (232300420099). 2025-02-04T14:50:36.9437158 2024-12-03T14:02:42.0438484 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemical Engineering Manying Liu 1 Pan Liu 2 Zikang Lei 3 Rongjuan Ba 4 Suxiang Ge 5 Jiachang Li 6 Huimin Jia 7 Yuanting Qiao 0000-0002-7741-9278 8 Yange Zhang 9 Zhi Zheng 10 68450__33409__9014c300c1f2482399dc07d27d300268.pdf APM-MS.pdf 2025-01-26T00:52:55.6260050 Output 927379 application/pdf Accepted Manuscript true Author accepted manuscript document released under the terms of a Creative Commons CC-BY licence using the Swansea University Research Publications Policy (rights retention). true eng https://creativecommons.org/licenses/by/4.0/deed.en
title Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
spellingShingle Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
Yuanting Qiao
title_short Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
title_full Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
title_fullStr Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
title_full_unstemmed Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
title_sort Phenanthrenequinone-Based Hyper-Cross-Linked Polymers via a Waste-Minimizing Friedel–Crafts Alkylation
author_id_str_mv ceae57100ecb7c4b2883e29079a8985d
author_id_fullname_str_mv ceae57100ecb7c4b2883e29079a8985d_***_Yuanting Qiao
author Yuanting Qiao
author2 Manying Liu
Pan Liu
Zikang Lei
Rongjuan Ba
Suxiang Ge
Jiachang Li
Huimin Jia
Yuanting Qiao
Yange Zhang
Zhi Zheng
format Journal article
container_title ACS Applied Polymer Materials
container_volume 6
container_issue 22
container_start_page 13805
publishDate 2024
institution Swansea University
issn 2637-6105
2637-6105
doi_str_mv 10.1021/acsapm.4c02663
publisher American Chemical Society (ACS)
college_str Faculty of Science and Engineering
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hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemical Engineering{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemical Engineering
document_store_str 1
active_str 0
description Although hyper-cross-linked polymers (HCPs) offer significant advantages, their industrial scalability has been impeded by concerns regarding waste generation. To mitigate this challenge, we have successfully developed an efficient and cost-effective green synthesis method for phenanthrenequinone-based HCPs (PQ-HCPs). This method employs a Friedel–Crafts alkylation reaction, utilizing trifluoromethanesulfonic acid as a catalyst and PQ as the starting material. Under low catalyst concentrations, electrophilic sulfonation reactions are predominant. However, increasing the catalyst to a 2 equiv amount significantly shifts the reaction pathway toward Friedel–Crafts alkylation cross-linking. The resultant optimal sample, PQ-HCP-1:3, boasts an impressive specific surface area of up to 428 m2·g–1. Dye adsorption experiments on these samples demonstrated a marked selective affinity for Rhodamine B, with the hydrophilicity of the samples being a pivotal factor in the adsorption process. This innovative approach substantially outperforms traditional methods, which typically involve ferric chloride (FeCl3) and aluminum chloride (AlCl3), by significantly reducing the production of solid waste and effluent during the chemical reaction process.
published_date 2024-11-22T08:25:51Z
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score 11.053243

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