Academic Journal
Competitive hydrogen bonding in supramolecular polymerizations of tribenzylbenzene-1,3,5-tricarboxamides
| العنوان: | Competitive hydrogen bonding in supramolecular polymerizations of tribenzylbenzene-1,3,5-tricarboxamides |
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| المؤلفون: | Mabesoone, Mathijs F. J., Kardas, Sinan, Soria-Carrera, Héctor, Barberá, Joaquín, Fuente, Jesús M. de la, Palmans, Anja R. A., Fossépré, Mathieu, Surin, Mathieu, Martín-Rapún, Rafael |
| المساهمون: | Netherlands Organization for Scientific Research, Ministry of Education, Culture and Science (The Netherlands), Ministerio de Ciencia, Innovación y Universidades (España), Ministerio de Economía y Competitividad (España), Ministerio de Educación, Cultura y Deporte (España), Fonds de la Recherche Scientifique (Fédération Wallonie-Bruxelles) |
| بيانات النشر: | Royal Society of Chemistry (UK) |
| سنة النشر: | 2020 |
| المجموعة: | Digital.CSIC (Consejo Superior de Investigaciones Científicas / Spanish National Research Council) |
| الوصف: | Despite numerous reports on nucleated supramolecular polymerization, the molecular origin of the properties of these supramolecular polymers remains overlooked. Here, the formation of fibers formed by self-assembly of N,N′,N′′-tris(alkoxybenzyl)benzene-1,3,5-tricarboxamides (benzyl-BTAs) has been studied using both simulations and experimental techniques. The simulations show that the fibers exhibit a dynamic behavior with stacking defects that appear and propagate differently depending on the BTA molecular structure. To validate theoretical results, a library of eight benzyl-BTAs has been synthesized to compare their supramolecular polymerizations both in the bulk and in apolar solvents. We show that the molecular organization of monomers and dynamics of supramolecular polymers strongly depend on the number and position of the alkoxy substituents on peripheral phenyl rings. By combining theoretical results with experimental measurements, we elucidate the likely role of competitive hydrogen bonding between the central amides and peripheral ether moieties on the stacking behavior of BTAs and the dynamics of structural defects in supramolecular polymers. Our findings open up new design rules for these dynamic materials. ; MFJM and ARAP thank E.W. (Bert) Meijer for stimulating discussions, Elisabeth Weyandt for providing several aldehyde starting materials, and acknowledge financial support from NWO (TOP-PUNT Grant 10018944) and the Dutch Ministry of Education, Culture and Science (Gravitation program 024.001.035). RMR, HSC, JB and JMF acknowledge the Ministerio de Ciencia Innovación y Universidades (Spain) for funding through the Ramón y Cajal Program (RYC-2013-12570) and Proyectos I+D+i (CTQ2015-66869-P). HSC is grateful for a FPU fellowship from Ministerio de Educación Cultura y Deporte (Spain). The collaboration between Eindhoven and Mons is supported by the Fonds de la Recherche Scientifique – FNRS and the Fonds Wetenschappelijk Onderzoek under EOS Project No. 30650939. Computational resources have been ... |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 2058-9689 |
| Relation: | #PLACEHOLDER_PARENT_METADATA_VALUE#; info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/RYC-2013-12570; info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-66869-P; Postprint; https://doi.org/10.1039/D0ME00030B; Sí; Molecular Systems Design and Engineering 5(4): 820-828 (2020); http://hdl.handle.net/10261/218895; http://dx.doi.org/10.13039/501100003176; http://dx.doi.org/10.13039/501100002661; http://dx.doi.org/10.13039/501100003329 |
| DOI: | 10.1039/D0ME00030B |
| DOI: | 10.13039/501100003176 |
| DOI: | 10.13039/501100002661 |
| DOI: | 10.13039/501100003329 |
| الاتاحة: | http://hdl.handle.net/10261/218895 https://doi.org/10.1039/D0ME00030B https://doi.org/10.13039/501100003176 https://doi.org/10.13039/501100002661 https://doi.org/10.13039/501100003329 |
| Rights: | open |
| رقم الانضمام: | edsbas.C9DF02F4 |
| قاعدة البيانات: | BASE |
| تدمد: | 20589689 |
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| DOI: | 10.1039/D0ME00030B |