Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization
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 carb...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-08-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/9/9/448 |
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| author | Yves L. Dory Mia Caron Vincent Olivier Duguay Lucas Chicoine-Ouellet Daniel Fortin Pierre Baillargeon |
| author_facet | Yves L. Dory Mia Caron Vincent Olivier Duguay Lucas Chicoine-Ouellet Daniel Fortin Pierre Baillargeon |
| author_sort | Yves L. Dory |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-11T20:56:13Z |
| format | Article |
| id | doaj.art-1d8da6049ae0428db325709bd59910f6 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-11T20:56:13Z |
| publishDate | 2019-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-1d8da6049ae0428db325709bd59910f62022-12-22T04:03:40ZengMDPI AGCrystals2073-43522019-08-019944810.3390/cryst9090448cryst9090448Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical PolymerizationYves L. Dory0Mia Caron1Vincent Olivier Duguay2Lucas Chicoine-Ouellet3Daniel Fortin4Pierre Baillargeon5Laboratoire de Synthèse Supramoléculaire, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e Avenue Nord, Sherbrooke, QC J1H 5N4, CanadaDépartement de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaDépartement de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaDépartement de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaLaboratoire d’Analyses Structurales par Diffraction des Rayons-X, Département de Chimie, Université de Sherbrooke, 2500, Boulevard de l’Université, Sherbrooke, QC J1K 2R1, CanadaDépartement de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, QC J1E 4K1, CanadaCrystal 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.https://www.mdpi.com/2073-4352/9/9/448biopolymersustainable materialspolydiacetylenefuranSingle Crystal X-ray Diffraction (SCXRD)carbamatehydrogen bondtopochemical polymerizationdiacetylene |
| spellingShingle | Yves L. Dory Mia Caron Vincent Olivier Duguay Lucas Chicoine-Ouellet Daniel Fortin Pierre Baillargeon Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization Crystals biopolymer sustainable materials polydiacetylene furan Single Crystal X-ray Diffraction (SCXRD) carbamate hydrogen bond topochemical polymerization diacetylene |
| title | Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization |
| title_full | Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization |
| title_fullStr | Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization |
| title_full_unstemmed | Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization |
| title_short | Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization |
| title_sort | preparation and single crystal structure determination of the first biobased furan polydiacetylene using topochemical polymerization |
| topic | biopolymer sustainable materials polydiacetylene furan Single Crystal X-ray Diffraction (SCXRD) carbamate hydrogen bond topochemical polymerization diacetylene |
| url | https://www.mdpi.com/2073-4352/9/9/448 |
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