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Open AccessArticle

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

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Laboratoire de Synthèse Supramoléculaire, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e Avenue Nord, Sherbrooke, QC J1H 5N4, Canada
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Département de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, QC J1E 4K1, Canada
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Laboratoire d’Analyses Structurales par Diffraction des Rayons-X, Département de Chimie, Université de Sherbrooke, 2500, Boulevard de l’Université, Sherbrooke, QC J1K 2R1, Canada
*
Author to whom correspondence should be addressed.
Crystals 2019, 9(9), 448; https://doi.org/10.3390/cryst9090448
Received: 31 July 2019 / Revised: 24 August 2019 / Accepted: 28 August 2019 / Published: 29 August 2019
Crystal structure elucidations of bio-based polymers provide invaluable data regarding structure–property relationships. In this work, we achieved synthesis and Single Crystal X-ray Diffraction (SCXRD) structural determination of a new furan-based polydiacetylene (PDA) derivative with carbamate (urethane) functionality. Firstly, diacetylene (DA) monomers were found to self-assemble in the crystalline state in such a way that the polymerization theoretically occurred in two different directions. Indeed, for both directions, geometrical parameters for the reactive alignment of DA are satisfied and closely related with the optimal geometrical parameters for DA topochemical polymerization (d(1) = 4.7–5.2 Å, d(2) ≤ 3.8 Å, θ ≈ 45°). However, within the axis of hydrogen bonds (HB), the self-assembling monomers display distances and angles (d(1) = 4.816 Å, d(2) = 3.822 Å, θ = 51°) that deviate more from the ideal values than those in the perpendicular direction (d(1) = 4.915Å, d(2) = 3.499Å, θ ≈ 45°). As expected from these observations, the thermal topochemical polymerization occurs in the direction perpendicular to the HB and the resulting PDA was characterized by SCXRD. View Full-Text
Keywords: biopolymer; sustainable materials; polydiacetylene; furan; Single Crystal X-ray Diffraction (SCXRD); carbamate; hydrogen bond; topochemical polymerization; diacetylene biopolymer; sustainable materials; polydiacetylene; furan; Single Crystal X-ray Diffraction (SCXRD); carbamate; hydrogen bond; topochemical polymerization; diacetylene
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MDPI and ACS Style

Dory, Y.L.; Caron, M.; Duguay, V.O.; Chicoine-Ouellet, L.; Fortin, D.; Baillargeon, P. Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization. Crystals 2019, 9, 448.

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