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  • 标题:A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy
  • 本地全文:下载
  • 作者:Micah Mabin ; Quintin Elliott ; Zhihan Wang
  • 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
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