Facile Modification of Propiolated Castor Oil via Nucleophilic Thiol‐Yne Click Reactions

IF 2.5 4区化学 Q3 POLYMER SCIENCE

Macromolecular Chemistry and Physics Pub Date : 2024-06-05 DOI:10.1002/macp.202400146

Damla Kalayci, Emre Akar, Serter Luleburgaz, E. Çakmakçi, U. Gunay, Volkan Kumbaraci, H. Durmaz, Umit Tunca

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引用次数: 0

Abstract

The combination of modern click protocols and bio‐based building blocks is a great step towards energy‐efficient, sustainable, and tailorable polymer production. Herein, we chose thiol‐Michael addition (thiol‐yne) reactions from the toolbox of click chemistry protocols and used propiolated castor oil (PCO), a vegetable oil derivative, as the bio‐based building block for the facile functionalization of PCO with various thiols. In addition to the functionalization of PCO, hyperbranched and crosslinked polymers were also prepared. The thiol‐yne click functionalization reactions of the PCO were conducted at room temperature within 5 minutes and in the presence of an organic catalyst. The modifications were conducted in 2‐MeTHF. The yields were found to change between 80–99% depending on the type of the thiol compound. The effect of various organic catalysts was investigated, and 1,8‐diazabicyclo(5.4.0)undec‐7‐ene (DBU) was found to be the most effective catalyst for the thiol‐yne modification reactions. The hyperbranched polymer reached 23.8 kDa (Mw) within 5 minutes. The thermosets displayed low glass transition temperatures (Tgs) between ‐46 °C and ‐26 °C. The findings of this paper open up new horizons for polymer researchers who work in the field of sustainable polymers and click chemistry and the presented idea here is appealing because it offers a potential strategy for fast, reliable, modular, and functional macromolecule preparation from renewable vegetable oils.This article is protected by copyright. All rights reserved

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通过亲核硫醇-炔单击反应对丙二醇化蓖麻油进行简便改性

现代点击化学协议与生物基构建模块的结合，是向高能效、可持续和可定制聚合物生产迈出的一大步。在此，我们从点击化学方案的工具箱中选择了硫醇-迈克尔加成（硫醇-炔）反应，并使用丙醇化蓖麻油（PCO）（一种植物油衍生物）作为生物基构建模块，用各种硫醇对 PCO 进行了简便的官能化。除了 PCO 的官能化之外，还制备了超支化和交联聚合物。PCO 的硫醇-炔单击官能化反应在室温和有机催化剂存在下于 5 分钟内进行。改性反应在 2-MeTHF 中进行。根据硫醇化合物类型的不同，产率在 80-99% 之间变化。研究发现，1,8-二氮杂双环(5.4.0)十一-7-烯（DBU）是硫醇-炔改性反应中最有效的催化剂。超支化聚合物的分子量在 5 分钟内达到 23.8 kDa。热固性塑料的玻璃化转变温度（Tgs）较低，介于 -46 °C 和 -26 °C 之间。本文的研究结果为可持续聚合物和点击化学领域的聚合物研究人员开辟了新的视野，本文提出的想法很有吸引力，因为它为利用可再生植物油制备快速、可靠、模块化和功能性大分子提供了一种潜在的策略。本文受版权保护。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Macromolecular Chemistry and Physics 化学-高分子科学

CiteScore

4.30

自引率

4.00%

发文量

278

审稿时长

1.4 months

期刊介绍： Macromolecular Chemistry and Physics publishes in all areas of polymer science - from chemistry, physical chemistry, and physics of polymers to polymers in materials science. Beside an attractive mixture of high-quality Full Papers, Trends, and Highlights, the journal offers a unique article type dedicated to young scientists – Talent.