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 (1O2), 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.
Highlights
Modern society is recording an urgent demand for sustainable, simple and selective synthetic methodologies for the preparation of smart materials and added value compounds (Corma et al, 2007; Kohli et al, 2019).In the polymer field, the interest for fully bio-based materials has enormously grown up, due to the urgent need to solve the serious environmental pollution problems caused by the extensive use of traditional fossil-based plastics
Complete conversion into a 1:1 mixture of regioisomers was obtained treating 1 with 1% Rose Bengal (RB), air and white light, while only starting material was recovered in absence of the photosensitizer
We studied the photooxygenation in the absence of solvent, after adsorption of 1 onto the photosensitizer/zeolite system, varying the nature of the photosensitizer and the zeolite, the loading of the photosensitizer on zeolite and the loading of substrate respect on photosensitizersupported zeolite
Summary
Modern society is recording an urgent demand for sustainable, simple and selective synthetic methodologies for the preparation of smart materials and added value compounds (Corma et al, 2007; Kohli et al, 2019).In the polymer field, the interest for fully bio-based materials has enormously grown up, due to the urgent need to solve the serious environmental pollution problems caused by the extensive use of traditional fossil-based plastics. Poly(butylene succinate) (PBS), synthesized through the well-known two-stage melt polycondensation reaction from 1,4-butanediol and succinic acid, has attracted much attention as promising ecofriendly bioplastic, being characterized by intriguing physical and mechanical properties, similar to those of polyethylene (LDPE), good processability, low cost, and biodegradability. Many works have been published describing the use of PBS in regenerative medicine and for the realization of nanosystems for controlled drug release (Gigli et al, 2016). In this context the biocompatibility of the material is crucial, and the straightforward
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