Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes
A series of triphenylene (TP) compounds—denoted 3,6-THTP-DiC<i>n</i>OH—bearing four hexyloxy ancillary chains and two variable-length alkoxy chains terminally functionalized with hydroxyl groups have been synthesized and characterized. The shorter homologs revealed mesogenic characterist...
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2024-12-01
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| author | Nahir Vadra Lisandro J. Giovanetti Pablo H. Di Chenna Fabio D. Cukiernik |
| author_facet | Nahir Vadra Lisandro J. Giovanetti Pablo H. Di Chenna Fabio D. Cukiernik |
| author_sort | Nahir Vadra |
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| description | A series of triphenylene (TP) compounds—denoted 3,6-THTP-DiC<i>n</i>OH—bearing four hexyloxy ancillary chains and two variable-length alkoxy chains terminally functionalized with hydroxyl groups have been synthesized and characterized. The shorter homologs revealed mesogenic characteristics, giving rise to thermotropic mesophases in which π-stacked columns of H-bound dimers self-organize yielding superstructures. Molecular-scale models are proposed to account for their structural features. The three studied compounds yielded supramolecular gels in methanol; their ability to gelify higher alcohols was found to be enhanced by the presence of water. The intermediate homolog also gelled <i>n</i>-hexane. Compared to their isomeric 2,7-THTP-DiC<i>n</i>OH analogs, the 3,6-derivatives showed a higher tendency to give rise to LC phases (wider thermal ranges) and a lower organogelling ability (variety of gelled solvents, lower gels stabilities). The overall results are analyzed in terms of different kinds of competing H-bonds: intramolecular, face-to-face dimeric, lateral polymeric, and solvent–TP interactions. |
| format | Article |
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| institution | Kabale University |
| issn | 2310-2861 |
| language | English |
| publishDate | 2024-12-01 |
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| series | Gels |
| spelling | doaj-art-d1c70e37ebb34c6cbc582d3c109dd4582025-01-24T13:33:45ZengMDPI AGGels2310-28612024-12-01111910.3390/gels11010009Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized TriphenylenesNahir Vadra0Lisandro J. Giovanetti1Pablo H. Di Chenna2Fabio D. Cukiernik3Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires C1428EGA, ArgentinaInstituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Universidad Nacional de la Plata, CONICET, La Plata B1900, ArgentinaUnidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (UMYMFOR), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, CONICET, Buenos Aires C1428EGA, ArgentinaDepartamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires C1428EGA, ArgentinaA series of triphenylene (TP) compounds—denoted 3,6-THTP-DiC<i>n</i>OH—bearing four hexyloxy ancillary chains and two variable-length alkoxy chains terminally functionalized with hydroxyl groups have been synthesized and characterized. The shorter homologs revealed mesogenic characteristics, giving rise to thermotropic mesophases in which π-stacked columns of H-bound dimers self-organize yielding superstructures. Molecular-scale models are proposed to account for their structural features. The three studied compounds yielded supramolecular gels in methanol; their ability to gelify higher alcohols was found to be enhanced by the presence of water. The intermediate homolog also gelled <i>n</i>-hexane. Compared to their isomeric 2,7-THTP-DiC<i>n</i>OH analogs, the 3,6-derivatives showed a higher tendency to give rise to LC phases (wider thermal ranges) and a lower organogelling ability (variety of gelled solvents, lower gels stabilities). The overall results are analyzed in terms of different kinds of competing H-bonds: intramolecular, face-to-face dimeric, lateral polymeric, and solvent–TP interactions.https://www.mdpi.com/2310-2861/11/1/9triphenylene functionalized triphenylenescolumnar liquid crystalsorganogelH-bonded dimers |
| spellingShingle | Nahir Vadra Lisandro J. Giovanetti Pablo H. Di Chenna Fabio D. Cukiernik Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes Gels triphenylene functionalized triphenylenes columnar liquid crystals organogel H-bonded dimers |
| title | Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes |
| title_full | Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes |
| title_fullStr | Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes |
| title_full_unstemmed | Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes |
| title_short | Columnar Mesophases and Organogels Formed by H-Bound Dimers Based on 3,6-Terminally Difunctionalized Triphenylenes |
| title_sort | columnar mesophases and organogels formed by h bound dimers based on 3 6 terminally difunctionalized triphenylenes |
| topic | triphenylene functionalized triphenylenes columnar liquid crystals organogel H-bonded dimers |
| url | https://www.mdpi.com/2310-2861/11/1/9 |
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