Publication: Imide-yne click polymerization: a new and versatile tool for the toolbox of X-yne click polymerization
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2024-01-01
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Abstract
The Michael reaction, a cornerstone in organic chemistry, continues to revolutionize the field with its unparalleled versatility in forming carbon-carbon, carbon-oxygen, carbon-nitrogen, and carbon-sulfur bonds, paving the way for groundbreaking advancements in complex molecule and macromolecule construction. In this study, imide-yne reaction was employed at the macromolecular level for the first time to prepare linear poly(imide ester)s. A wide range of bisimides and dipropiolates were reacted through imide-yne click polymerization in the presence of 1,4-diazabicyclo[2.2.2] octane (DABCO) at room temperature. The polymerizations proceed in an anti-Markovnikov fashion, yielding the E-isomer as the major product. Polymers were obtained in high yields and their molecular weights were found to be in the range of 5.64-12.67 kDa. The remaining unreacted double bonds in the linear polymers were found to undergo further functionalization with thiols using a strong organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), which was also supported by a model study. Post-polymerization modification study prompted us to prepare imide-yne monomers that can react with dithiols to synthesize poly(imide thioether)s through nucleophilic thiol-ene click reaction using TBD as the catalyst. The obtained polymers displayed a wide range of glass transition temperatures and thermal stability. Thus, it can be said that the proposed method enables the synthesis of new polyimide-based structures with tailorable thermal properties. It is believed that the proposed strategy will make a significant contribution to expanding the versatility of active alkyne chemistry at the macromolecular level.
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Biyomedikal Mühendisliği, Yaşam Bilimleri, Moleküler Biyoloji ve Genetik, Sitogenetik, Kimya, Biyokimya, Biyoinorganik Kimya, Fizikokimya, Polimer Karakterizasyonu, Temel Bilimler, Mühendislik ve Teknoloji, Biomedical Engineering, Life Sciences, Molecular Biology and Genetics, Cytogenetic, Chemistry, Biochemistry, Bioinorganic Chemistry, Physical Chemistry, Characterization of Polymers, Natural Sciences, Engineering and Technology, Mühendislik Bilişim Ve Teknoloji (Eng), Temel Bilimler (Sci), Yaşam Bilimleri (Life), Mühendislik, Moleküler Biyoloji Ve Genetik, Mühendislik Biyomedikal, Polimer Bilimi, Kimya Organik, Biyokimya Ve Moleküler Biyoloji, Engineering Computing & Technology (Eng), Natural Sciences (Sci), Life Sciences (Life), Engineering, Molecular Biology & Genetics, Engineering Biomedical, Polymer Science, Chemistry Organic, Biochemistry & Molecular Biology, Biyomühendislik, Fizik Bilimleri, Polimerler ve Plastikler, Organik Kimya, Bioengineering, Physical Sciences, Polymers and Plastics, Organic Chemistry
Citation
Aslanturk O., Sagdic G., ÇAKMAKÇI E., Durmaz H., Günay U. S., "Imide-yne click polymerization: a new and versatile tool for the toolbox of X-yne click polymerization", Polymer Chemistry, 2024