Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems
One of the challenges in fullerene chemistry is to prepare derivatives soluble in common solvents to study their chemical and physical properties in solution. In this context, a new highly soluble fullerene adduct was synthesized by the cycloaddition of a hydrazone-aldehyde derivative, which is pre...
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| Format: | Article |
| Language: | English |
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Academia Colombiana de Ciencias Exactas, Físicas y Naturales
2023-08-01
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| Series: | Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales |
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| Online Access: | https://raccefyn.co/index.php/raccefyn/article/view/1903 |
| _version_ | 1797737512864579584 |
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| author | Gabriel Martinez Christian C. Carmona Vargas Manuel N. Chaur |
| author_facet | Gabriel Martinez Christian C. Carmona Vargas Manuel N. Chaur |
| author_sort | Gabriel Martinez |
| collection | DOAJ |
| description |
One of the challenges in fullerene chemistry is to prepare derivatives soluble in common solvents to study their chemical and physical properties in solution. In this context, a new highly soluble fullerene adduct was synthesized by the cycloaddition of a hydrazone-aldehyde derivative, which is prepared from the condensation of pyridincarboxaldehyde and pyridinhydrazine derivatives, and C60 in the presence of N-octyl glycine. The hydrazone derivative acting as a 1,3-dipole and [60] fullerene as a dipolarophile yielded adduct 7 with a 32% yield. The synthesized compounds were characterized by nuclear magnetic resonance (NMR) spectroscopy (1H, 13C, and COSY), elemental analysis, and mass spectrometry. The electronic properties of the fullerene adduct 7 were analyzed by UV-Vis spectroscopy in toluene and compared to those of [60]fullerene. The electrochemical properties of the fulleropyrrolidine were studied using cyclic and square wave voltammetry in tetrahydrofuran (THF) showing three reduction peaks at -1.11, -1.70, and -2.28 V, which are cathodically shifted when compared to [60]fullerene.
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| first_indexed | 2024-03-12T13:30:28Z |
| format | Article |
| id | doaj.art-6fd57c3cd92f4392b87e11c84405580a |
| institution | Directory Open Access Journal |
| issn | 0370-3908 2382-4980 |
| language | English |
| last_indexed | 2024-03-12T13:30:28Z |
| publishDate | 2023-08-01 |
| publisher | Academia Colombiana de Ciencias Exactas, Físicas y Naturales |
| record_format | Article |
| series | Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales |
| spelling | doaj.art-6fd57c3cd92f4392b87e11c84405580a2023-08-24T15:08:12ZengAcademia Colombiana de Ciencias Exactas, Físicas y NaturalesRevista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales0370-39082382-49802023-08-01Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systemsGabriel Martinez0Christian C. Carmona Vargas1Manuel N. Chaur2 Departamento de Química, Universidad del Valle, Cali, Colombia Departamento de Química, Universidad del Valle, Cali, ColombiaDepartamento de Química, Universidad del Valle, Cali, Colombia. Centro de Excelencia en Nuevos Materiales (CENM), Universidad del Valle, Cali, Colombia One of the challenges in fullerene chemistry is to prepare derivatives soluble in common solvents to study their chemical and physical properties in solution. In this context, a new highly soluble fullerene adduct was synthesized by the cycloaddition of a hydrazone-aldehyde derivative, which is prepared from the condensation of pyridincarboxaldehyde and pyridinhydrazine derivatives, and C60 in the presence of N-octyl glycine. The hydrazone derivative acting as a 1,3-dipole and [60] fullerene as a dipolarophile yielded adduct 7 with a 32% yield. The synthesized compounds were characterized by nuclear magnetic resonance (NMR) spectroscopy (1H, 13C, and COSY), elemental analysis, and mass spectrometry. The electronic properties of the fullerene adduct 7 were analyzed by UV-Vis spectroscopy in toluene and compared to those of [60]fullerene. The electrochemical properties of the fulleropyrrolidine were studied using cyclic and square wave voltammetry in tetrahydrofuran (THF) showing three reduction peaks at -1.11, -1.70, and -2.28 V, which are cathodically shifted when compared to [60]fullerene. https://raccefyn.co/index.php/raccefyn/article/view/1903Fullerenes HydrazonesPyrrolidine [60]fullereneCyclic voltammetry |
| spellingShingle | Gabriel Martinez Christian C. Carmona Vargas Manuel N. Chaur Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales Fullerenes Hydrazones Pyrrolidine [60]fullerene Cyclic voltammetry |
| title | Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems |
| title_full | Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems |
| title_fullStr | Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems |
| title_full_unstemmed | Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems |
| title_short | Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems |
| title_sort | design synthesis and electrochemical studies of a new 60 fullerene pyrrolidine as a precursor for the construction of supramolecular systems |
| topic | Fullerenes Hydrazones Pyrrolidine [60]fullerene Cyclic voltammetry |
| url | https://raccefyn.co/index.php/raccefyn/article/view/1903 |
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