Substituted glycolides from natural sources: preparation, alcoholysis and polymerization

Nifant'ev, I.E.; Shlyakhtin, A.V.; Bagrov, V.V.; Tavtorkin, A.N.; Komarov, P.D.; Churakov, A.V.; Ivchenko, P.V.

Статья опубликована в высокорейтинговом журнале

Информация о цитировании статьи получена из Web of Science, Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 16 декабря 2020 г.

Авторы: Nifant'ev Ilya E., Shlyakhtin Andrey V., Bagrov Vladimir V., Tavtorkin Alexander N., Komarov Pavel D., Churakov Andrei V., Ivchenko Pavel V.
Журнал: Polymer Chemistry
Том: 11
Номер: 42
Год издания: 2020
Первая страница: 6890
Последняя страница: 6902
DOI: 10.1039/d0py01297a
Аннотация: Polylactides, polyglycolides and copolymers containing both glycolate and lactate fragments are biocompatible and biodegradable materials that can be used for environmentally friendly packaging, 3D printing, surgery, drug delivery and other applications. Here we present a first comparative study of a series of 1,4-dioxan-2,5-diones (glycolides: MeGL, iPrGL, iBuGL, BnGL, PhGL and MePhGL) that can be synthesized from natural L-α-hydroxy acids or L-α-amino acids. The formation of (R,R)(S,S)-MePhGL was confirmed by X-ray diffractometry and explained using density functional theory (DFT). We found that diester fragments are retained during the non-catalytic methanolysis of these compounds and that ring-opening regoiselectivitydepends on the bulkiness of the substituents. Ring-opening polymerization, catalyzed by 1,5,7-triazabicyclo[4.4.0]undec-5-ene, yielded alkyl-substituted polyglycolides with given MWs. Controlled polymerization of PhGL was possible at low monomer/initiator ratios, while (R,R)/(S,S)-MePhGL formed oligomers and epimerized products. DFT modeling provided an explanation for the observed patterns based on the ease of enolization and the stability of the enolate-anions of phenyl-substituted glycolides. Solutions of MeGL, iPrGL, iBuGL, BnGL and PhGL homopolymers in hexafluoroisopropanol were electrospun into fibrous mats whose morphologies, mechanical characteristics, biodegradabilities and thermal properties varied widely and depended on the substituents on the glycolide.
Добавил в систему: Нифантьев Илья Эдуардович

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Substituted glycolides from natural sources: preparation, alcoholysis and polymerizationстатья

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