Eugenol Biobased\nPolydiacetylene

Eugenol, a natural compound with numerous biological\nactivities,\ncan be extracted from plants or obtained by depolymerizing lignin.\nIt is also a prime building block for the design of biobased resins\nand polymers. As the transition from conventional to eco-friendly\nelectronics is underway, new green synthetic approaches are being\ndeveloped to obtain π-conjugated polymers. Therefore, the potential\nfor using eugenol in this context caught our attention. Herein, we\nreport the synthesis and single-crystal structural determination of\na eugenol-based diacetylene (Eug-DA) monomer grafted with a carbamate\nmoiety to achieve the stacking required for polymerization. The characteristic\nblue-violet color of polydiacetylenes (PDA) appears when DA monomer\nsingle crystals are left in ambient light or subjected to X-ray or\nUV irradiation. Similar blue-purple PDA crystals were also obtained\nby leaving a DA sample for 1 month at room temperature away from light.\nThe characteristic peaks of PDA in Raman spectroscopy were observed,\nas were the usual thermochromism and solvatochromism properties of\nPDA.

Publication Details

Journal
Figshare
Published
2024-10-01
DOI
https://doi.org/10.1021/acs.cgd.4c00888.s001
Primary Topic
Polydiacetylene-based materials and applications
Type
article
Field-Weighted Citation Impact
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article

Eugenol Biobased\nPolydiacetylene

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Polydiacetylene-based materials and applications
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Eugenol Biobased\nPolydiacetylene

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Abstract

Eugenol, a natural compound with numerous biological\nactivities,\ncan be extracted from plants or obtained by depolymerizing lignin.\nIt is also a prime building block for the design of biobased resins\nand polymers. As the transition from conventional to eco-friendly\nelectronics is underway, new green synthetic approaches are being\ndeveloped to obtain π-conjugated polymers. Therefore, the potential\nfor using eugenol in this context caught our attention. Herein, we\nreport the synthesis and single-crystal structural determination of\na eugenol-based diacetylene (Eug-DA) monomer grafted with a carbamate\nmoiety to achieve the stacking required for polymerization. The characteristic\nblue-violet color of polydiacetylenes (PDA) appears when DA monomer\nsingle crystals are left in ambient light or subjected to X-ray or\nUV irradiation. Similar blue-purple PDA crystals were also obtained\nby leaving a DA sample for 1 month at room temperature away from light.\nThe characteristic peaks of PDA in Raman spectroscopy were observed,\nas were the usual thermochromism and solvatochromism properties of\nPDA.

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Polydiacetylene-based materials and applications
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