{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T17:30:30Z","timestamp":1787074230178,"version":"build-2736575974"},"reference-count":37,"publisher":"American Chemical Society (ACS)","issue":"32","license":[{"start":{"date-parts":[[2026,8,2]],"date-time":"2026-08-02T00:00:00Z","timestamp":1785628800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100020108","name":"Fuji Seal Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100020108","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Degradable adhesives that are both strong and cleanly debondable are highly desirable for progressing sustainable materials but are challenging to develop owing to the limited availability of polymer systems that are endowed with both sufficient cohesion and interfacial interactions. Herein, we report a series of novel P(METATFSI-co-BMDO) polymers as a new class of cationic-side-chain-bearing aromatic polyester synthesized via radical ring-opening copolymerization of [2-(methacryloyloxy)ethyl]trimethylammonium bis(trifluoromethanesulfonyl)imide (METATFSI), an ionic-liquid monomer, and 5,6-benzo-2-bromomethyl-1,3-dioxepane (BMDO), an aromatic cyclic ketene acetal. Incorporating BMDO endows the polymer backbone with ester linkages that facilitate main-chain degradability, while the combination of its aromatic units and dense cationic side chains provides pronounced cation\u2212\u03c0 interactions. The use of the ionic-liquid monomer significantly enhances the BMDO-polymerization efficiency to afford copolymers in high yields and with tunable compositions. Strong cation\u2212\u03c0 interactions are evidenced by lower solubilities and higher glass transition temperatures compared to those predicted by ideal mixing, indicative of superior cohesive interactions within the polymer matrix. Adhesion testing revealed that P(METATFSI-co-BMDO) is strongly adhesive toward aluminum as well as challenging low-surface-energy substrates, including polypropylene and polytetrafluoroethylene. Intermediate copolymer compositions led to optimal adhesion, which reflects a balance between cohesive strengthening via cation\u2212\u03c0 interactions and effective interfacial adhesion through ionic and dipolar interactions. Hence, radical ring-opening copolymerization is a powerful strategy for integrating cation\u2212\u03c0 interactions into degradable polyester adhesives, thereby offering a promising platform for high-performance, sustainable adhesive materials that are applicable to a wide range of substrates.<\/jats:p>","DOI":"10.1021\/acsomega.6c06129","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:35:32Z","timestamp":1785854132000},"page":"48634-48641","source":"Crossref","is-referenced-by-count":0,"title":["Adhesive Properties\nof Aromatic Polyesters with Cationic\nSide Chains Synthesized via Radical Ring-Opening Copolymerization"],"prefix":"10.1021","volume":"11","author":[{"given":"Gaku","family":"Sugimoto","sequence":"first","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshiaki","family":"Kobayashi","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7014-390X","authenticated-orcid":true,"given":"Syuuhei","family":"Komatsu","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]},{"name":"Josai University , , ,","place":["Sakado, Japan, 350-0295"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8857-3185","authenticated-orcid":true,"given":"Shohei","family":"Shiomoto","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]},{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7814-3656","authenticated-orcid":true,"given":"Akihiko","family":"Kikuchi","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]},{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9087-5174","authenticated-orcid":true,"given":"Taka-Aki","family":"Asoh","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Tokyo, Japan, 125-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,2]]},"reference":[{"key":"2026081811131789200_cit1","doi-asserted-by":"publisher","first-page":"8240","DOI":"10.1039\/D3CS00764B","article-title":"Eduardo Saiz \u201cNature-inspired\nadhesive systems\u201d","volume":"53","author":"Li","year":"2024","journal-title":"Chem. Soc. Rev."},{"key":"2026081811131789200_cit2","doi-asserted-by":"publisher","first-page":"1030","DOI":"10.1038\/s41563-023-01577-2","article-title":"Metamaterial adhesives\nfor programmable adhesion through reverse crack propagation","volume":"22","author":"Hwang","year":"2023","journal-title":"Nat. Mater."},{"key":"2026081811131789200_cit3","doi-asserted-by":"publisher","first-page":"306","DOI":"10.1038\/s41586-023-06335-7","article-title":"Sustainably sourced\ncomponents to\ngenerate high-strength adhesives","volume":"621","author":"Westerman","year":"2023","journal-title":"Nature"},{"key":"2026081811131789200_cit4","doi-asserted-by":"publisher","first-page":"36","DOI":"10.1039\/D1GC03306A","article-title":"Debondable\nadhesives and their use in recycling","volume":"24","author":"Mulcahy","year":"2022","journal-title":"Green\nChem."},{"key":"2026081811131789200_cit5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202419498","article-title":"Degradable\nAdhesives as Sustainable Alternatives to\nAcrylics via Ring-Opening Radical Polymerization of Vinylcyclopropanes","volume":"64","author":"Kim","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081811131789200_cit6","doi-asserted-by":"publisher","first-page":"8473","DOI":"10.1021\/acs.chemrev.4c00032","article-title":"Designed to\nDegrade: Tailoring Polyesters for Circularity","volume":"124","author":"Aarsen","year":"2024","journal-title":"Chem. Rev."},{"key":"2026081811131789200_cit7","doi-asserted-by":"publisher","first-page":"1177","DOI":"10.1038\/s41428-024-00948-z","article-title":"Molecular design of reactive polycaprolactone\nthat can be induced into shape-memory materials promotes further functionalization","volume":"56","author":"Yoshida","year":"2024","journal-title":"Polym. J."},{"key":"2026081811131789200_cit8","doi-asserted-by":"publisher","first-page":"1171","DOI":"10.1021\/acs.accounts.2c00068","article-title":"Principles of Cation\u2212\u03c0 Interactions for\nEngineering\nMussel-Inspired Functional Materials","volume":"55","author":"Geng","year":"2022","journal-title":"Acc. 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Rev."},{"key":"2026081811131789200_cit18","doi-asserted-by":"publisher","first-page":"6879","DOI":"10.1021\/acs.langmuir.5b01149","article-title":"Surface-functionalized\nbiodegradable nanoparticles consisting of amphiphilic graft polymers\nprepared by radical copolymerization of 2-methylene-1,3-dioxepane\nand macromonomers","volume":"31","author":"Asoh","year":"2015","journal-title":"Langmuir"},{"key":"2026081811131789200_cit19","doi-asserted-by":"publisher","first-page":"68","DOI":"10.1016\/j.polymer.2017.09.073","article-title":"Facile preparation\nof degradable thermoresponsive polymers as biomaterials: Thermoresponsive\npolymers prepared by radical polymerization degrade to water-soluble\noligomers","volume":"130","author":"Komatsu","year":"2017","journal-title":"Polymer"},{"key":"2026081811131789200_cit20","doi-asserted-by":"publisher","first-page":"3981","DOI":"10.1021\/acs.langmuir.8b00148","article-title":"Fabrication\nof hybrid capsules via CaCO3 crystallization on degradable\ncoacervate droplets","volume":"34","author":"Komatsu","year":"2018","journal-title":"Langmuir"},{"key":"2026081811131789200_cit21","doi-asserted-by":"publisher","first-page":"1016","DOI":"10.1021\/acsmacrolett.4c00295","article-title":"Fast and Selective\nMain-Chain Scission of Vinyl Polymers Using the Domino Reaction in\nthe Alternating Sequence for Transesterification","volume":"13","author":"Kohsaka","year":"2024","journal-title":"ACS Macro Lett."},{"key":"2026081811131789200_cit22","doi-asserted-by":"publisher","first-page":"5829","DOI":"10.1039\/D2PY00986B","article-title":"Mechanistic investigation of cyclic\nketene acetal radical\nring-opening homo- and co-polymerization and preparation of PEO graft\ncopolymers with tunable composition","volume":"13","author":"Du","year":"2022","journal-title":"Polym.\nChem."},{"key":"2026081811131789200_cit23","doi-asserted-by":"publisher","first-page":"1368","DOI":"10.1039\/b204319j","article-title":"Conventional free\nradical polymerization in room temperature ionic liquids: a green\napproach to commodity polymers with practical advantages","author":"Hong","year":"2002","journal-title":"Chem. 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Mater. Chem."},{"key":"2026081811131789200_cit30","doi-asserted-by":"publisher","first-page":"905","DOI":"10.1002\/macp.200900579","article-title":"Synthetic Route and Characterization\nof Main Chain Ester-Containing Hydrolytically Degradable Poly(N,N-dimethylaminoethyl methacrylate)-Based\nPolycations","volume":"211","author":"Agarwal","year":"2010","journal-title":"Macromol. Chem. Phys."},{"key":"2026081811131789200_cit31","doi-asserted-by":"publisher","first-page":"3152","DOI":"10.1016\/j.matlet.2008.02.008","article-title":"Prediction\nof glass transition temperatures: Binary blends and copolymers","volume":"62","author":"Brostow","year":"2008","journal-title":"Mater. Lett."},{"key":"2026081811131789200_cit32","doi-asserted-by":"publisher","first-page":"9485","DOI":"10.1021\/acs.jpcb.5c03909","article-title":"Impact of Monomer\nSequence and Interaction\nParameter on Polymer Glass Transition Temperature","volume":"129","author":"Taylor","year":"2025","journal-title":"J. Phys. Chem. B"},{"key":"2026081811131789200_cit33","doi-asserted-by":"publisher","first-page":"128","DOI":"10.1039\/D2SM01229D","article-title":"Effect\nof the polar group content on the glass transition temperature of\nROMP copolymers","volume":"19","author":"Li","year":"2022","journal-title":"Soft Matter"},{"key":"2026081811131789200_cit34","doi-asserted-by":"publisher","first-page":"3452","DOI":"10.1021\/acsapm.9b00871","article-title":"Polymer surface\noxidation by light activated chlorine dioxide radical for metal-plastics\nadhesion","volume":"1","author":"Jia","year":"2019","journal-title":"ACS Applied Polymer Materials"},{"key":"2026081811131789200_cit35","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202523689","article-title":"Fluoride-Free\nAdhesives for Low Surface\nEnergy Fluorinate Substrates","volume":"36","author":"Zheng","year":"2026","journal-title":"Adv. Funct. Mater."},{"key":"2026081811131789200_cit36","doi-asserted-by":"publisher","first-page":"31653","DOI":"10.1039\/C5CP05873B","article-title":"Contact\nangles and wettability of\nionic liquids on polar and non-polar surfaces","volume":"17","author":"Pereira","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026081811131789200_cit37","doi-asserted-by":"publisher","first-page":"5676","DOI":"10.1002\/adma.201201780","article-title":"Joining the Un-Joinable:\nAdhesion Between Low Surface Energy Polymers Using Tetrapodal ZnO\nLinkers","volume":"24","author":"Jin","year":"2012","journal-title":"Adv. Mater."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c06129","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/32\/48634\/66354610\/acsomega.6c06129.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/32\/48634\/66354610\/acsomega.6c06129.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T17:21:39Z","timestamp":1787073699000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/32\/48634\/5238331\/Adhesive-Properties-of-Aromatic-Polyesters-with"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,2]]},"references-count":37,"journal-issue":{"issue":"32","published-online":{"date-parts":[[2026,8,2]]},"published-print":{"date-parts":[[2026,8,18]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c06129","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,2]]}}}