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Aggregation and Emission Modulations of Two-Component Gel Phase Systems Induced by H-Bonds

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Abstract

A novel organogelator, named 4-[3,4,5-Tris(dodecyloxy)benzoyloxy]-4׳-stilbazole (12TSB), was successfully synthesized through mild reaction conditions. The synthesis involved the utilization of 4-Hydroxy-4′-stilbazole, 3,4,5-tridodecyloxylbenzoic acid, and DCC/HOBt as dehydration reagents, resulting in a high yield of the desired compound. To obtain 1,3,5-Tris(4-amidobutanoic acid)phenylbenzene (TABAPB), a mixture of 1,3,5-tri(4-aminophenyl)benzene and three equivalents of succinic anhydride was stirred in THF at room temperature for 24 h. The reaction proceeded to produce TABAPB as the desired product. The synthesized stilbazole derivative, 12TSB, exhibited the ability to form gel phases when dissolved in alcoholic solvents and DMSO, owing to the interactions facilitated by л–л (pi–pi) and Van der Waals forces. The resulting gel materials displayed distinct physical properties, which varied depending on the solvent used. Complex systems were prepared by dissolving l-Tartaric acid, along with 2 equivalents of 12TSB or TABAPB, in dry THF, followed by subsequent solvent evaporation. The derivatives of the complex systems formed gel phases, and their properties were modulated based on the potential complementary interactions of H-bonding and л-л stacking. Characterization of these systems through UV–Vis, 1H-NMR, and fluorescence emission tests revealed that the modulation of optical properties primarily originated from the formation of either H-type or J-type aggregations. The specific type of aggregation observed was dictated by the nature of the two interacting components, acting as H-donor–acceptor pairs. This study contributes to a deeper understanding of the self-assembly process by elucidating the development of gelation and its impact on the modulation of optical properties.

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Acknowledgements

The authors are greatly thankful to State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, PR China.

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  1. Laboratoire de Chimie Organique et des Substances Naturelles, Faculté des Sciences, Université de Lomé, 01 BP 1515 Lomé 01, Lomé, Togo

    Oudjaniyobi Simalou

  2. State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, 130012, People’s Republic of China

    Oudjaniyobi Simalou & Ran Lu

  3. Laboratoire de Chimie Organique et des Sciences de l’Environnement, Faculté des Sciences et Techniques, Université de Kara, BP 404, Kara, Togo

    Kodjo Eloh

  4. Laboratoire de Génie des Procédés et Ressources Naturelles (LAGEPREN), Faculté des Sciences, Université de Lomé, 01 BP 1515 Lomé 01, Lomé, Togo

    Agbekonyi Kokou Agbodan

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OS and RL are responsible of conceptualization, OS software treatments, OS, KE, AKA and RL writing-original draft preparation, OS and RL validation, RL supervision. All authors read and approved the final manuscript.

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Simalou, O., Eloh, K., Agbodan, A.K. et al. Aggregation and Emission Modulations of Two-Component Gel Phase Systems Induced by H-Bonds. Chemistry Africa 7, 301–313 (2024). https://doi.org/10.1007/s42250-023-00731-2

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