Lanteri Deianira, Quattrosoldi Silvia, Soccio Michelina, Basso Andrea, Cavallo Dario, Munari Andrea, Riva Renata, Lotti Nadia, Moni Lisa
Department of Chemistry and Industrial Chemistry, University of Genova, Genova, Italy.
Department of Civil, Chemical, Environmental and Materials Engineering, University of Bologna, Bologna, Italy.
Front Chem. 2020 Feb 13;8:85. doi: 10.3389/fchem.2020.00085. eCollection 2020.
Dye-sensitized photooxygenation reaction of bio-based double bond-containing substrates is proposed as sustainable functionalization of terpenes and terpenoids to transform them into polyoxygenated compounds to be employed for the synthesis of new bio-based polyesters. As proof of concept, citronellol has been regioselectively converted into diol using singlet oxygen (O), a traceless reagent that can be generated from air, visible light and zeolite supported-photosensitizer (Thionine-NaY). With our synthetic approach, diol has been obtained in two-steps, with good regioselectivity, using green reagents such as light and air, and finally a solvent-free oxidation step. From this compound, a citronellol-based copolyester of poly(butylene succinate) (PBS) has been synthesized and fully characterized. The results obtained evidence that the proposed copolymerization of PBS with the citronellol-based building blocks allows to obtain a more flexible and functionalizable material, by exploiting a largely available natural molecule modified through a green synthetic path.
基于生物的含双键底物的染料敏化光氧化反应被认为是萜类化合物和萜烯类化合物的可持续官能化方法，可将它们转化为多氧化合物，用于合成新型生物基聚酯。作为概念验证，香茅醇已使用单线态氧（O）进行区域选择性转化为二醇，单线态氧是一种可由空气、可见光和沸石负载的光敏剂（硫堇-NaY）产生的无痕试剂。通过我们的合成方法，使用光和空气等绿色试剂，通过两步反应以良好的区域选择性获得了二醇，最后是无溶剂氧化步骤。由该化合物合成了基于香茅醇的聚丁二酸丁二醇酯（PBS）共聚酯，并进行了全面表征。获得的结果表明，通过利用经绿色合成途径改性的大量可用天然分子，将PBS与基于香茅醇的结构单元进行共聚可以得到更具柔韧性和功能性的材料。
