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EnglishDye-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 1 has been regioselectively converted into diol 4 using singlet oxygen (O-1(2)), a traceless reagent that can be generated from air, visible light and zeolite supported-photosensitizer (Thionine-NaY). With our synthetic approach, diol 4 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.
| Titolo: | Regioselective Photooxidation of Citronellol: A Way to Monomers for Functionalized Bio-Polyesters |
| Autore/i: | Lanteri, Deianira; Quattrosoldi, Silvia; Soccio, Michelina; Basso, Andrea; Cavallo, Dario; Munari, Andrea; Riva, Renata; Lotti, Nadia; Moni, Lisa |
| Autore/i Unibo: | |
| Anno: | 2020 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.3389/fchem.2020.00085 |
| Abstract: | 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 1 has been regioselectively converted into diol 4 using singlet oxygen (O-1(2)), a traceless reagent that can be generated from air, visible light and zeolite supported-photosensitizer (Thionine-NaY). With our synthetic approach, diol 4 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. |
| Data stato definitivo: | 2020-04-21T23:34:40Z |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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