Boivin Louis-Philippe, Dupont William, Leclerc Mario, Gendron David
Université Laval, Département de Chimie, Québec City G1V 0A6, Canada.
Cégep de Thetford, Kemitek, Thetford Mines G6G 0A5, Canada.
J Org Chem. 2021 Dec 3;86(23):16548-16557. doi: 10.1021/acs.joc.1c01869. Epub 2021 Nov 12.
Forest biomass is viewed as a significant source of organic carbon and thus the ideal replacement of petroleum products. From the resources derived from biomass, lignocellulose is the most abundant biobased material on earth. One of the aromatic added value compounds obtained from the depolymerization of lignin is vanillin. Here, we report the preparation of new compounds having benzothiophene, indole, isatin, benzofuroxan, benzofurazan, benzothiadiazole, and phthalimide heteroaromatic ring structures. More precisely, our results show that vanillin can be used as a biosourced starting material for the preparation of a variety of aromatic dibrominated monomers. X-ray crystallography on single crystals was also performed to obtain meaningful information on their solid-state ordering. This work opens the way to new, sustainable, biosourced aromatic materials (small molecules or polymers) for organic electronics.
森林生物质被视为有机碳的重要来源，因此是石油产品的理想替代品。在源自生物质的资源中，木质纤维素是地球上最丰富的生物基材料。从木质素解聚得到的一种芳香族增值化合物是香草醛。在此，我们报告了具有苯并噻吩、吲哚、异吲哚酮、苯并呋咱、苯并呋喃嗪、苯并噻二唑和邻苯二甲酰亚胺杂芳环结构的新化合物的制备。更确切地说，我们的结果表明香草醛可用作制备各种芳香族二溴化单体的生物源起始材料。还对单晶进行了X射线晶体学分析，以获取有关其固态有序性的有意义信息。这项工作为有机电子学开辟了通往新型、可持续、生物源芳香材料（小分子或聚合物）的道路。
