000132238 001__ 132238
000132238 005__ 20251121145033.0
000132238 0247_ $$2doi$$a10.1039/D3QO01832F
000132238 0248_ $$2sideral$$a136611
000132238 037__ $$aART-2024-136611
000132238 041__ $$aeng
000132238 100__ $$aGonzález, Lucía
000132238 245__ $$aHydantoin hexameric rosettes: harnessing H-bonds for supergelation and liquid crystals
000132238 260__ $$c2024
000132238 5060_ $$aAccess copy available to the general public$$fUnrestricted
000132238 5203_ $$aWe 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.
000132238 536__ $$9info:eu-repo/grantAgreement/ES/MINECO/PID2021-122882NB-I00$$9info:eu-repo/grantAgreement/ES/MINECO-FEDER/PGC2018-097583-B-I00$$9info:eu-repo/grantAgreement/ES/MICINN/RYC2021-031154-I$$9info:eu-repo/grantAgreement/ES/DGA/E47-23R
000132238 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc$$uhttps://creativecommons.org/licenses/by-nc/4.0/deed.es
000132238 590__ $$a4.7$$b2024
000132238 592__ $$a1.068$$b2024
000132238 591__ $$aCHEMISTRY, ORGANIC$$b5 / 57 = 0.088$$c2024$$dQ1$$eT1
000132238 593__ $$aOrganic Chemistry$$c2024$$dQ1
000132238 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000132238 700__ $$aMarín, Iván$$uUniversidad de Zaragoza
000132238 700__ $$0(orcid)0000-0003-1141-5933$$aTejedor, Rosa M.$$uUniversidad de Zaragoza
000132238 700__ $$0(orcid)0000-0001-5816-7960$$aBarberá, Joaquín$$uUniversidad de Zaragoza
000132238 700__ $$0(orcid)0000-0003-1378-0571$$aRomero, Pilar
000132238 700__ $$0(orcid)0000-0002-8932-9085$$aConcellón, Alberto$$uUniversidad de Zaragoza
000132238 700__ $$0(orcid)0000-0001-7636-9187$$aUriel, Santiago$$uUniversidad de Zaragoza
000132238 700__ $$aSerrano, José L.
000132238 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000132238 773__ $$g11, 3 (2024), 735-745$$pOrganic chemistry frontiers.$$tORGANIC CHEMISTRY FRONTIERS$$x2052-4129
000132238 8564_ $$s2093113$$uhttps://zaguan.unizar.es/record/132238/files/texto_completo.pdf$$yVersión publicada
000132238 8564_ $$s2799959$$uhttps://zaguan.unizar.es/record/132238/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000132238 909CO $$ooai:zaguan.unizar.es:132238$$particulos$$pdriver
000132238 951__ $$a2025-11-21-14:41:08
000132238 980__ $$aARTICLE