Abstract
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.
Highlights
Biomass and biomass-derived materials are considered by the scientific community as some of the most promising alternatives for decreasing the current dependence on fossil resources [1,2,3,4,5,6]
This is evidenced by plans to gradually replace some petroleum-based plastic by bio-based plastic [7,8,9,10,11,12]
There are several reasons that can explain the growing interest in furan-based polymers: (1) they originate from lignocellulose, the most abundant and bio-renewable biomass on earth [1]; (2) the synthetic accessibility of a wide variety of furan monomers with very different chemical properties, providing access to various types of macromolecular materials such as polyesters, polyamides, polyurethanes, epoxy resins, etc., [18]; and (3) the possibility of exploiting the chemical features associated with the Crystals 2019, 9, 448; doi:10.3390/cryst9090448
Summary
Biomass and biomass-derived materials are considered by the scientific community as some of the most promising alternatives for decreasing the current dependence on fossil resources [1,2,3,4,5,6]. This is evidenced by plans to gradually replace some petroleum-based plastic by bio-based plastic [7,8,9,10,11,12]. Development of new bio-based polymers requires characterization tools to gain better. X-ray understanding thewidely material's structure andThese properties [26].tools
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