Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands
Organic amines are important compounds present in a wide variety of products, which makes the development of new systems for their detection an interesting field of study. New organometallic complexes of group 9 [MCp*X(2′-R-2-py-SBF)] (M = Ir, Rh; R = H, X = Cl (<b>6</b>), R = H, X = OAc...
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MDPI AG
2023-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/20/7155 |
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| author | Krystal M. Cid-Seara Raquel Pereira-Cameselle Sandra Bolaño Maria Talavera |
| author_facet | Krystal M. Cid-Seara Raquel Pereira-Cameselle Sandra Bolaño Maria Talavera |
| author_sort | Krystal M. Cid-Seara |
| collection | DOAJ |
| description | Organic amines are important compounds present in a wide variety of products, which makes the development of new systems for their detection an interesting field of study. New organometallic complexes of group 9 [MCp*X(2′-R-2-py-SBF)] (M = Ir, Rh; R = H, X = Cl (<b>6</b>), R = H, X = OAc (<b>7</b>), R = CHO, X = Cl (<b>8</b>)), and [IrCp*Cl(2′, 7-diCHO-2-py-SBF)] (<b>9</b>) (Cp* pentamethylcyclopentadienyl, SBF = 9,9’-spirobifluorene) bearing bidentate C–N ligands based on 9,9′-spirobifluorene were obtained and characterized by NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray diffraction analysis when possible. The formation of a Schiff base to give complexes with the formula [MCp*Cl(2′-CH=NR-2-py-SBF)] (M = Ir, Rh; R = alkyl or aryl (<b>10</b>–<b>12</b>)), through condensation of an amine, and the aldehyde group present in these new complexes was studied leading to a selective reactivity depending on the nature of the amine and the metal center. While the iridium complexes only react with aromatic amines, the rhodium derivative requires heat for those but can react at room temperature with aliphatic amines. |
| first_indexed | 2024-03-10T21:01:07Z |
| format | Article |
| id | doaj.art-e7fe924cb0ab46009cb0f44e01453ebe |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T21:01:07Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e7fe924cb0ab46009cb0f44e01453ebe2023-11-19T17:33:35ZengMDPI AGMolecules1420-30492023-10-012820715510.3390/molecules28207155Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene LigandsKrystal M. Cid-Seara0Raquel Pereira-Cameselle1Sandra Bolaño2Maria Talavera3Departamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, SpainDepartamento de Química Orgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, SpainDepartamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, SpainDepartamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, SpainOrganic amines are important compounds present in a wide variety of products, which makes the development of new systems for their detection an interesting field of study. New organometallic complexes of group 9 [MCp*X(2′-R-2-py-SBF)] (M = Ir, Rh; R = H, X = Cl (<b>6</b>), R = H, X = OAc (<b>7</b>), R = CHO, X = Cl (<b>8</b>)), and [IrCp*Cl(2′, 7-diCHO-2-py-SBF)] (<b>9</b>) (Cp* pentamethylcyclopentadienyl, SBF = 9,9’-spirobifluorene) bearing bidentate C–N ligands based on 9,9′-spirobifluorene were obtained and characterized by NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray diffraction analysis when possible. The formation of a Schiff base to give complexes with the formula [MCp*Cl(2′-CH=NR-2-py-SBF)] (M = Ir, Rh; R = alkyl or aryl (<b>10</b>–<b>12</b>)), through condensation of an amine, and the aldehyde group present in these new complexes was studied leading to a selective reactivity depending on the nature of the amine and the metal center. While the iridium complexes only react with aromatic amines, the rhodium derivative requires heat for those but can react at room temperature with aliphatic amines.https://www.mdpi.com/1420-3049/28/20/7155iridiumrhodiumspirobifluoreneamines |
| spellingShingle | Krystal M. Cid-Seara Raquel Pereira-Cameselle Sandra Bolaño Maria Talavera Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands Molecules iridium rhodium spirobifluorene amines |
| title | Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands |
| title_full | Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands |
| title_fullStr | Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands |
| title_full_unstemmed | Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands |
| title_short | Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands |
| title_sort | selective schiff base formation of group 9 organometallic complexes with functionalized spirobifluorene ligands |
| topic | iridium rhodium spirobifluorene amines |
| url | https://www.mdpi.com/1420-3049/28/20/7155 |
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