Aniket A. Talanikar, Samadhan S. Nagane, Prakash P. Wadgaonkar, Gajanan S. Rashinkar
{"title":"降冰片烯基悬垂芳香(co)聚醚醚酮","authors":"Aniket A. Talanikar, Samadhan S. Nagane, Prakash P. Wadgaonkar, Gajanan S. Rashinkar","doi":"10.1080/10601325.2023.2261462","DOIUrl":null,"url":null,"abstract":"Abstract4, 4'-(Bicyclo (2.2.1) hept-5-en-2 yl methylene) bis (2-methoxyphenol) (BPA-NB) was utilized as a step-growth monomer for the synthesis of (co)poly(ether ether ketone)s (PEEK-NBs) via nucleophilic aromatic substitution polycondensation. A homo and five PEEK-NBs were synthesized by polycondensation of 4, 4'-difluorobenzophenone with BPA-NB and various compositions of BPA-NB and bisphenol-A, respectively. 1H NMR spectroscopy confirmed the chemical structure and composition of PEEK-NBs. Inherent viscosity and number-average molecular weight values of PEEK-NBs were in the range 0.64 to 0.78 dL g−1 and 62,670 to 84,470 g mol−1, respectively, indicating the formation of polymers of reasonably high molecular weight. It was easy to dissolve PEEK-NBs in common organic solvents such as chloroform, dichloromethane, and tetrahydrofuran. Tough, transparent, and flexible films of PEEK-NBs could be cast from chloroform solution. X-Ray diffraction studies indicated amorphous nature of PEEK-NBs. Glass transition temperature (Tg) values, determined by DSC analysis, of PEEK-NBs were in the range 163 to190 °C and Tg values increased with the increase in mol % of BPA-NB. The post-polymerization modification of a representative PEEK-NB was demonstrated using two azido compounds, namely, 4-(azidomethyl)-7-methoxy-2H-chromen-2-one and 9-(azidomethyl)anthracene, via metal-free azide-alkene 1,3-dipolar cycloaddition reaction to obtain copoly(ether ether ketone)s appended with coumarinyl and anthracenyl moieties, respectively.Keywords: (Co)poly(ether ether ketone)snorbornenyl groupspost-polymerization modificationazide-alkene click reaction AcknowledgementsAuthors are grateful to Dr. P. R. Rajamohanan for help with interpretation of NMR data.Disclosure statementNo potential conflict of interest was reported by the author(s).","PeriodicalId":50159,"journal":{"name":"Journal of Macromolecular Science Part A-Pure and Applied Chemistry","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2023-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Norbornenyl-pendant aromatic (co)poly(ether ether ketone)s\",\"authors\":\"Aniket A. Talanikar, Samadhan S. Nagane, Prakash P. Wadgaonkar, Gajanan S. Rashinkar\",\"doi\":\"10.1080/10601325.2023.2261462\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Abstract4, 4'-(Bicyclo (2.2.1) hept-5-en-2 yl methylene) bis (2-methoxyphenol) (BPA-NB) was utilized as a step-growth monomer for the synthesis of (co)poly(ether ether ketone)s (PEEK-NBs) via nucleophilic aromatic substitution polycondensation. A homo and five PEEK-NBs were synthesized by polycondensation of 4, 4'-difluorobenzophenone with BPA-NB and various compositions of BPA-NB and bisphenol-A, respectively. 1H NMR spectroscopy confirmed the chemical structure and composition of PEEK-NBs. Inherent viscosity and number-average molecular weight values of PEEK-NBs were in the range 0.64 to 0.78 dL g−1 and 62,670 to 84,470 g mol−1, respectively, indicating the formation of polymers of reasonably high molecular weight. It was easy to dissolve PEEK-NBs in common organic solvents such as chloroform, dichloromethane, and tetrahydrofuran. Tough, transparent, and flexible films of PEEK-NBs could be cast from chloroform solution. X-Ray diffraction studies indicated amorphous nature of PEEK-NBs. Glass transition temperature (Tg) values, determined by DSC analysis, of PEEK-NBs were in the range 163 to190 °C and Tg values increased with the increase in mol % of BPA-NB. 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Abstract4, 4'-(Bicyclo (2.2.1) hept-5-en-2 yl methylene) bis (2-methoxyphenol) (BPA-NB) was utilized as a step-growth monomer for the synthesis of (co)poly(ether ether ketone)s (PEEK-NBs) via nucleophilic aromatic substitution polycondensation. A homo and five PEEK-NBs were synthesized by polycondensation of 4, 4'-difluorobenzophenone with BPA-NB and various compositions of BPA-NB and bisphenol-A, respectively. 1H NMR spectroscopy confirmed the chemical structure and composition of PEEK-NBs. Inherent viscosity and number-average molecular weight values of PEEK-NBs were in the range 0.64 to 0.78 dL g−1 and 62,670 to 84,470 g mol−1, respectively, indicating the formation of polymers of reasonably high molecular weight. It was easy to dissolve PEEK-NBs in common organic solvents such as chloroform, dichloromethane, and tetrahydrofuran. Tough, transparent, and flexible films of PEEK-NBs could be cast from chloroform solution. X-Ray diffraction studies indicated amorphous nature of PEEK-NBs. Glass transition temperature (Tg) values, determined by DSC analysis, of PEEK-NBs were in the range 163 to190 °C and Tg values increased with the increase in mol % of BPA-NB. The post-polymerization modification of a representative PEEK-NB was demonstrated using two azido compounds, namely, 4-(azidomethyl)-7-methoxy-2H-chromen-2-one and 9-(azidomethyl)anthracene, via metal-free azide-alkene 1,3-dipolar cycloaddition reaction to obtain copoly(ether ether ketone)s appended with coumarinyl and anthracenyl moieties, respectively.Keywords: (Co)poly(ether ether ketone)snorbornenyl groupspost-polymerization modificationazide-alkene click reaction AcknowledgementsAuthors are grateful to Dr. P. R. Rajamohanan for help with interpretation of NMR data.Disclosure statementNo potential conflict of interest was reported by the author(s).
期刊介绍:
Journal of Macromolecular Science, Part A: Pure and Applied Chemistry (JMS-PAC) is a necessary resource for academic and industrial scientists and engineers whose interests center on both synthetic and naturally occurring polymers and their applications.