文章基本信息

标题：A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy
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作者：Micah Mabin ; Quintin Elliott ; Zhihan Wang 等
期刊名称：iScience
印刷版ISSN：2589-0042
出版年度：2022
卷号：25
期号：9
页码：1-13
DOI：10.1016/j.isci.2022.105020
语种：English
出版社：Elsevier
摘要：SummaryA novel cyclobutane-containing diacid building block, CBDA-3, was synthesized from sorbic acid using clean, efficient [2 + 2] photocycloaddition. This photoreaction can be performed using commercially available germicidal lamps, which represent a form of ECO-UV. SC-XRD showed that the cyclobutane ring in CBDA-3 has a unique semi-rigid character, unlike more rigid aromatic rings or more flexible types of aliphatic rings. C=C bonds present in the structure of CBDA-3 provide opportunities for derivatization which could be used to alter the characteristics of polymers made from this monomer. Additionally, TGA and DSC analysis showed CBDA-3 to have excellent thermal stability. These characteristics make CBDA-3 a promising building block with the potential to be used as a sustainable alternative to traditional petroleum-derived diacids. Finally, a facile and reliable Fischer esterification of CBDA-3 was performed to tune its melting point and solubility for different applications and to demonstrate the applicability of this building block in polymer synthesis.Graphical abstractDisplay OmittedHighlights•A novel cyclobutane-containing diacid building block•A potentially sustainable alternative to petroleum-derived diacids•Photoreaction using ECO-UV (Energy-efficient, Cost-effective, and Operator-friendly)Chemistry; Organic chemistry; Green chemistry