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This work was supported by the MINECO-FEDER funds PGC2018-097583-B-I00, PID2021-122882NB-I00 and PID2021-126132-NB-I00 (MCIN/AEI/10.13039/501100011033/and by "ERDF A way of making Europe") and Gobierno de Aragon-FEDER (Research Group E47_23R). A. C. acknowledges grant RYC2021-031154-I funded by the MICINN/AEI/FEDER/EU-NextGenerationEU. The authors would like to acknowledge the use of the SAI (UZ), CEQMA (UZ-CSIC) Services and the Laboratorio de Microscopias Avanzadas-LMA (INMA-UZ).

Analysis of institutional authors

Gonzalez, LuciaAuthor

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Article

Hydantoin hexameric rosettes: harnessing H-bonds for supergelation and liquid crystals

Publicated to:Organic Chemistry Frontiers. 11 (3): 735-745 - 2023-12-04 11(3), DOI: 10.1039/d3qo01832f

Authors: Gonzalez, Lucia; Marin, Ivan; Tejedor, Rosa M; Barbera, Joaquin; Romero, Pilar; Concellon, Alberto; Uriel, Santiago; Serrano, Jose L

Affiliations

Abstract

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. We present two hydantoin isomers that self-assemble through hydrogen bonding in solution and in bulk, either in a bowl-shaped or planar rosette, resulting in remarkable liquid crystals and gelation properties.

Keywords

AciAggregationAssembliesComplexMobilityPatterns

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Organic Chemistry Frontiers due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2023, it was in position 6/58, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Organic. Notably, the journal is positioned above the 90th percentile.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2025-06-08:

  • WoS: 2
  • Scopus: 2
  • OpenCitations: 1

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-06-08:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 7.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 7 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 1.
  • The number of mentions on the social network X (formerly Twitter): 2 (Altmetric).

Leadership analysis of institutional authors

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: First Author (González Bermúdez, Lucía) .