{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T05:03:12Z","timestamp":1787029392337,"version":"build-2736575974"},"reference-count":32,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2022,9,19]],"date-time":"2022-09-19T00:00:00Z","timestamp":1663545600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Opening Foundation of Heilongjiang Provincial Key Laboratory of Polymeric Composition materials","award":["CLKFKT2021Z1"],"award-info":[{"award-number":["CLKFKT2021Z1"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Polymers"],"abstract":"<jats:p>Polyether ketone (PEK) plastics are linear thermoplastic polymers connected by at least one ether bond and at least one ketone bond on the aryl group. The reason for their excellent heat resistance, rigidity, and mechanical strength is that their main molecular chain contains plenty of aromatic rings and polar carbonyl groups, and their molecular chain presents a large rigidity and strong intermolecular force. In addition, the main chain contains a considerable number of ether bonds, resulting in a certain toughness. However, polyether ketone materials have the disadvantage of poor solubility because of their excellent rigidity. To improve the solubility of polyether ketone, the preparation method of a novel nitrogenous heterocyclic polyaromatic ether monomer, 2-(4-chlorophenyl)-2,3-dihydrophthalazine-1,4-dione (CDD), was proposed, and its activity of polymerization was studied. The average molecular weight of the poly(aryl ether ketone) containing a nitrogenous heterocyclic polyaromatic ether group obtained by self-polycondensation of CDD was 4.181 \u00d7 103 kg\/mol, and the yield was 90.5%. In order to further explore the activity of monomers, novel copolymerized poly(aryl ether ketone) (PBCD) containing a nitrogenous heterocyclic polyaromatic ether structure was prepared by ternary copolymerization with 4,4-difluorobenzophenone (DFBP) and bisphenol fluorene (BHPF) with high activity. The average molecular weight of PBCD was 72.793 \u00d7 103 kg\/mol, the molecular weight distribution was 2.344, and the yield was 88.1%. Fourier transform infrared spectroscopy (FT-IR) and 1H NMR were used to confirm the structure of the obtained polymer. Through thermogravimetric analysis (TGA), the determined weight loss temperature of 5% under nitrogen was higher than 500 \u00b0C, indicating excellent thermal stability. Compared with the solubility of the binary copolymer containing fluorenyl poly(aryl ether ketone) (PBD), the polymer showed reasonable solubility in selective solvents such as chloroform and N,N-dimethylacetamide.<\/jats:p>","DOI":"10.3390\/polym14183904","type":"journal-article","created":{"date-parts":[[2022,9,19]],"date-time":"2022-09-19T04:49:22Z","timestamp":1663562962000},"page":"3904","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis and Characterization of a Self-Polycondensation Diazaphthalanone Monomer and Its Polymers from Polycondensation Reactions"],"prefix":"10.3390","volume":"14","author":[{"given":"Xin","family":"Liu","sequence":"first","affiliation":[{"name":"College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar 161006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaozhou","family":"Zhang","sequence":"additional","affiliation":[{"name":"College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar 161006, China"},{"name":"Heilongjiang Province Key Laboratory of Polymeric Composition Material, Qiqihar 161006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiawei","family":"Jiang","sequence":"additional","affiliation":[{"name":"College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar 161006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongge","family":"Jia","sequence":"additional","affiliation":[{"name":"College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar 161006, China"},{"name":"Heilongjiang Province Key Laboratory of Polymeric Composition Material, Qiqihar 161006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xigao","family":"Jian","sequence":"additional","affiliation":[{"name":"Department of Polymer Science & Engineering, Dalian University of Technology, Dalian 116024, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinyan","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Polymer Science & Engineering, Dalian University of Technology, Dalian 116024, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"22439","DOI":"10.1039\/C8NR07548D","article-title":"Robust polyimide nanofibrous membrane with porous-layer-coated morphology by in situ self-bonding and micro-crosslinking for lithium-ion battery separator","volume":"10","author":"Sun","year":"2018","journal-title":"Nanoscale"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"486","DOI":"10.1016\/j.progpolymsci.2013.11.002","article-title":"Multifunctional polymer foams with carbon nanoparticles","volume":"39","author":"Antunes","year":"2014","journal-title":"Prog. Polym. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1016\/j.jiec.2015.03.013","article-title":"A review on colorless and optically transparent polyimide films: Chemistry, process and engineering applications","volume":"28","author":"Ni","year":"2015","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"414","DOI":"10.1002\/pola.22392","article-title":"Synthesis, characterization, and properties of new thermally curable polyetheresters containing benzoxazine moieties in the main chain","volume":"46","author":"Kiskan","year":"2010","journal-title":"J. Polym. Sci. Part A Polym. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1691","DOI":"10.1021\/ma047973u","article-title":"Synthesis and CO2 Solubility Studies of Poly(ether carbonate)s and Poly(ether ester)s Produced by Step Growth Polymerization","volume":"38","author":"Tan","year":"2005","journal-title":"Macromolecules"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1002\/app.1912","article-title":"Synthesis and properties of novel poly(phthalazinone ether ketone ketone)","volume":"82","author":"Liu","year":"2001","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1467","DOI":"10.1007\/s00289-012-0866-z","article-title":"Synthesis of poly (arylene ether nitrile ketone) s bearing phthalazinone moiety and their properties","volume":"70","author":"Wang","year":"2013","journal-title":"Polym. Bull."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"858","DOI":"10.1002\/pi.4857","article-title":"Carbazole-based poly(aryl ether ketone) containing crosslinkable allyl groups on the side chains: Synthesis, characterization and properties","volume":"64","author":"Wang","year":"2015","journal-title":"Polym. Int."},{"key":"ref_9","first-page":"148","article-title":"Polymers derived from phenolphthaleins","volume":"34","author":"Berard","year":"1993","journal-title":"Polym. Prepr. (Am. Chem. Soc. Div. Pol. Chem.)"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1021\/ma030246z","article-title":"Synthesis and characterization of phthalazinone containing poly(arylene ether)s via a novel N-C coupling reaction","volume":"37","author":"Wang","year":"2012","journal-title":"Macromolecules"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1882","DOI":"10.1007\/s11051-013-1882-0","article-title":"Synthesis and characterization of Zn-doped MgAl-layered double hydroxide nanoparticles as PVC heat stabilizer","volume":"15","author":"Wang","year":"2013","journal-title":"J. Nanoparticle Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1007\/s10800-011-0313-0","article-title":"Chemical and mechanical degradation of sulfonated poly(sulfone) membranes in vanadium redox flow batteries","volume":"41","author":"Zhang","year":"2011","journal-title":"J. Appl. Electrochem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/j.memsci.2010.02.064","article-title":"Effect of amination agent on the properties of quaternized poly(phthalazinone ether sulfone) anion exchange membrane for vanadium redox flow battery application","volume":"354","author":"Xing","year":"2010","journal-title":"J. Membr. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1286","DOI":"10.1021\/am100146u","article-title":"High-temperature poly(phthalazinone ether ketone) thin films for dielectric energy storage","volume":"2","author":"Pan","year":"2010","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1016\/j.memsci.2008.10.047","article-title":"Synthesis of fluoro-containing sulfonated poly(phthalazinone ether ketone ketone)s and their properties as PEM in PEMFC and DMFC","volume":"326","author":"Pan","year":"2009","journal-title":"J. Membr. Sci."},{"key":"ref_16","first-page":"3724","article-title":"Chemically derived graphene\u2013metal oxide hybrids as electrodes for electrochemical energy storage: Pre-graphenization or post-graphenization?","volume":"19","author":"Chen","year":"2012","journal-title":"J. Mater. Chem."},{"key":"ref_17","first-page":"783","article-title":"New advances in the research of carbazole compounds","volume":"30","author":"Zhang","year":"2010","journal-title":"Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2327","DOI":"10.1016\/j.polymer.2012.03.056","article-title":"Soluble semi-crystalline PEEK analogs based on 3,5-difluorobenzophenone: Synthesis and characterization","volume":"53","author":"Fortney","year":"2012","journal-title":"Polymer"},{"key":"ref_19","first-page":"379","article-title":"Properties of Poly(arylene ether ketone)s Containing N-Alkylcarbazole in Main Chains","volume":"32","author":"Wang","year":"2015","journal-title":"Appl. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1177\/0954008319901148","article-title":"New poly(aryl ether ketone)s containing 2,6-diphenylpyridyl units and diphenylphosphinophenyl pendant groups","volume":"32","author":"Zhang","year":"2020","journal-title":"High Perform. Polym."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Bao, F., Zhang, F., Wang, C., Song, Y., Li, N., Wang, J., and Jian, X. (2019). Study of the Effects of the Structure of Phthalazinone\u2019s Side-Group on the Properties of the Poly(phthalazinone ether ketone)s Resins. Polymers, 11.","DOI":"10.3390\/polym11050803"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1007\/s10965-019-1812-7","article-title":"Novel benzimidazole and pyridine-containing poly(ether ether ketone) s with good solubility, thermal properties and fluorescence","volume":"26","author":"Deng","year":"2019","journal-title":"J. Polym. Res."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"742","DOI":"10.1002\/pat.1950","article-title":"Synthesis and characterization of phthalazinone-based poly(aryl ether ketone) derived from 4,4\u2032-dichlorobenzophenone","volume":"23","author":"Zhou","year":"2012","journal-title":"Polym. Adv. Technol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1761","DOI":"10.1002\/pola.27199","article-title":"Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB-type monomers","volume":"52","author":"Li","year":"2014","journal-title":"J. Polym. Sci. Part A Polym. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1080\/10601320601077039","article-title":"Synthesis of High Molecular Weight Fluorinated Poly(phthalazinone ether)s by Self-Condensation of an AB-Type Monomer and by Condensation of AA Monomers with Decafluorobiphenyl","volume":"44","author":"Li","year":"2007","journal-title":"J. Macromol. Sci. Part A Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"122525","DOI":"10.1016\/j.polymer.2020.122525","article-title":"Effect of pendent phenyl and bis-phthalazinone moieties on the properties of N-heterocyclic poly(aryl ether ketone ketone)s","volume":"198","author":"Liu","year":"2020","journal-title":"Polymer"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.polymer.2015.02.015","article-title":"Production and characterization of melt-spun Poly(Ether Ether Ketone) fibers for biomedical applications","volume":"63","author":"Ouellette","year":"2015","journal-title":"Polymer"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1051","DOI":"10.1080\/10601325.2010.511080","article-title":"Synthesis and Properties of Carbazole-containing Copolymers from Bis [3-(4-fluorobenzoyl)carbazole] Methane","volume":"47","author":"Liu","year":"2010","journal-title":"J. Macromol. Sci. Part A"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"100696","DOI":"10.1016\/j.mtcomm.2019.100696","article-title":"Crosslinkable polyaryletherketone ultrafiltration membranes with solvent-resistant improvement","volume":"21","author":"Jin","year":"2019","journal-title":"Mater. Today Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"50895","DOI":"10.1002\/app.50895","article-title":"Heat resistant microporous membranes based on soluble poly (aryl ether ketone) copolymers for lithium ion battery separator","volume":"138","author":"Huang","year":"2021","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1994","DOI":"10.1016\/0032-3861(85)90179-X","article-title":"On the molecular weight determination of a poly(aryl-ether-ether-ketone) (PEEK)","volume":"26","author":"Devaux","year":"1985","journal-title":"Polymer"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"110205","DOI":"10.1016\/j.eurpolymj.2020.110205","article-title":"Poly(aryl ether ketone ketone)s containing diphenyl-biphthalazin-dione moieties with excellent thermo-mechanical performance and solubility","volume":"143","author":"Liu","year":"2020","journal-title":"Eur. Polym. J."}],"container-title":["Polymers"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4360\/14\/18\/3904\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:34:04Z","timestamp":1760142844000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4360\/14\/18\/3904"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,19]]},"references-count":32,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["polym14183904"],"URL":"https:\/\/doi.org\/10.3390\/polym14183904","relation":{},"ISSN":["2073-4360"],"issn-type":[{"value":"2073-4360","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,9,19]]}}}