101515 20230926093531.0 doi 10.1039/d0me00030b sideral 118316 ART-2020-118316 eng Mabesoone, M.F.J. Competitive hydrogen bonding in supramolecular polymerizations of tribenzylbenzene-1, 3, 5-tricarboxamides 2020 Access copy available to the general public Unrestricted 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. info:eu-repo/grantAgreement/ES/MCIU/RYC-2013-12570 info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2015-66869-P info:eu-repo/semantics/openAccess All rights reserved http://www.europeana.eu/rights/rr-f/ 4.935 2020 CHEMISTRY, PHYSICAL 57 / 162 = 0.352 2020 Q2 T2 NANOSCIENCE & NANOTECHNOLOGY 52 / 106 = 0.491 2020 Q2 T2 MATERIALS SCIENCE, MULTIDISCIPLINARY 106 / 333 = 0.318 2020 Q2 T1 1.355 2020 Biomedical Engineering 2020 Q1 Chemical Engineering (miscellaneous) 2020 Q1 Chemistry (miscellaneous) 2020 Q1 Process Chemistry and Technology 2020 Q1 Industrial and Manufacturing Engineering 2020 Q1 Materials Chemistry 2020 Q1 Energy Engineering and Power Technology 2020 Q1 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion Kardas, S. Soria-Carrera, H. (orcid)0000-0002-5823-0314 Barbera, J. Universidad de Zaragoza (orcid)0000-0001-5816-7960 Martinez de la Fuente, J. (orcid)0000-0003-1081-8482 Palmans, A.R.A. Fossepre, M. Surin, M. Martin-Rapun, R. Universidad de Zaragoza (orcid)0000-0003-0702-8260 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 5, 4 (2020), 820-828 MOLECULAR SYSTEMS DESIGN & ENGINEERING 2058-9689 1323315 http://zaguan.unizar.es/record/101515/files/texto_completo.pdf Postprint 1178221 http://zaguan.unizar.es/record/101515/files/texto_completo.jpg?subformat=icon icon Postprint oai:zaguan.unizar.es:101515 articulos driver 2023-09-26-09:29:59 ARTICLE