132238 20260217205503.0 doi 10.1039/D3QO01832F sideral 136611 ART-2024-136611 eng González, Lucía Hydantoin hexameric rosettes: harnessing H-bonds for supergelation and liquid crystals 2024 Access copy available to the general public Unrestricted We have synthesized two geometric isomers of a cyclohexane-5-spirohydantoin derivative (1,3-diazaspiro[4.5]decane-2,4-dione) incorporating a hydrophobic phenyl 3,4,5-tris(dodecyloxy)benzoate unit at position 8. Separation of these diastereomers was accomplished through silica gel flash chromatography. The interplay of intermolecular hydrogen bonding and micro-segregation between the polar hydantoin unit and nonpolar aliphatic chains within the molecule endows them with remarkable self-assembly capabilities, both in solution and in the solid state. These hydantoin derivatives spontaneously form rosette-shaped structures composed of six molecules. In the solid state, these compounds display hexagonal columnar liquid crystal phases, with hydrogen-bonded disks as their fundamental building blocks. Similarly, when exposed to apolar solvents such as cyclohexane or dodecane, they adopt a columnar arrangement, resulting in gel formation comprising nanoscale fibers that intricately interlace to form a network. Remarkably, the two isomers exhibit markedly different properties. The major isomer behaves as a glassy liquid crystalline material, while the minor one exhibits liquid crystalline behavior with a high propensity to crystallize. Our experimental findings, in combination with theoretical studies, underscore the fundamentally distinct supramolecular organizations present in these isomers, shedding light on their unique self-assembling properties. info:eu-repo/grantAgreement/ES/DGA/E47-23R info:eu-repo/grantAgreement/ES/MICINN/RYC2021-031154-I info:eu-repo/grantAgreement/ES/MINECO-FEDER/PGC2018-097583-B-I00 info:eu-repo/grantAgreement/ES/MINECO/PID2021-122882NB-I00 info:eu-repo/semantics/openAccess by-nc https://creativecommons.org/licenses/by-nc/4.0/deed.es 4.7 2024 CHEMISTRY, ORGANIC 5 / 57 = 0.088 2024 Q1 T1 1.068 2024 Organic Chemistry 2024 Q1 8.2 2024 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Marín, Iván Universidad de Zaragoza Tejedor, Rosa M. Universidad de Zaragoza (orcid)0000-0003-1141-5933 Barberá, Joaquín Universidad de Zaragoza (orcid)0000-0001-5816-7960 Romero, Pilar (orcid)0000-0003-1378-0571 Concellón, Alberto Universidad de Zaragoza (orcid)0000-0002-8932-9085 Uriel, Santiago Universidad de Zaragoza (orcid)0000-0001-7636-9187 Serrano, José L. 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 11, 3 (2024), 735-745 Organic chemistry frontiers. ORGANIC CHEMISTRY FRONTIERS 2052-4129 2093113 http://zaguan.unizar.es/record/132238/files/texto_completo.pdf Versión publicada 2799959 http://zaguan.unizar.es/record/132238/files/texto_completo.jpg?subformat=icon icon Versión publicada oai:zaguan.unizar.es:132238 articulos driver 2026-02-17-20:22:42 ARTICLE