Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers
The utilization of dodecaborate boron clusters, [B<sub>12</sub>X<sub>12</sub>]<sup>2−</sup> (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkyl...
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2024-12-01
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| author | Satoshi Yamamoto Hibiki Nakamura Yumiko K. Kawamura Taro Kitazawa Mutsumi Kimura Yu Kitazawa |
| author_facet | Satoshi Yamamoto Hibiki Nakamura Yumiko K. Kawamura Taro Kitazawa Mutsumi Kimura Yu Kitazawa |
| author_sort | Satoshi Yamamoto |
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| description | The utilization of dodecaborate boron clusters, [B<sub>12</sub>X<sub>12</sub>]<sup>2−</sup> (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkylation of [B<sub>12</sub>Br<sub>11</sub>OH]<sup>2−</sup> to functionalize it with an aliphatic spacer was developed with a view to expanding the known chemical space of membrane carriers based on [B<sub>12</sub>Br<sub>12</sub>]<sup>2−</sup>. A new and improved facile route for the preparation of [B<sub>12</sub>Br<sub>11</sub>OH]<sup>2−</sup>, which is an important precursor to other [B<sub>12</sub>Br<sub>11</sub>OR]<sup>2−</sup> species, is reported. Various alkoxylated [B<sub>12</sub>Br<sub>11</sub>O(CH<sub>2</sub>)<sub>5</sub>Z]<sup>2−</sup> (Z = OH, N(CO)<sub>2</sub>C<sub>6</sub>H<sub>4</sub>, CN and N<sub>3</sub>) derivatives were prepared via a divergent synthesis based on [B<sub>12</sub>Br<sub>11</sub>O(CH<sub>2</sub>)<sub>5</sub>Br]<sup>2−</sup>. One of the newly synthesized compounds was utilized as a membrane carrier, and its impact on cell viability was examined. |
| format | Article |
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| language | English |
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| spelling | doaj-art-3e9095fcb694453494b67f772425f9702025-08-20T02:00:35ZengMDPI AGChemistry2624-85492024-12-01661635164410.3390/chemistry6060099Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic SpacersSatoshi Yamamoto0Hibiki Nakamura1Yumiko K. Kawamura2Taro Kitazawa3Mutsumi Kimura4Yu Kitazawa5Department of Chemistry and Materials, Faculty of Textile Science and Technology, Shinshu University, Ueda 386-8567, JapanDepartment of Chemistry and Materials, Faculty of Textile Science and Technology, Shinshu University, Ueda 386-8567, JapanDepartment of Molecular Biology and Genetics, Aarhus University, Universitetsbyen 81, 8000 Aarhus, DenmarkDepartment of Molecular Biology and Genetics, Aarhus University, Universitetsbyen 81, 8000 Aarhus, DenmarkDepartment of Chemistry and Materials, Faculty of Textile Science and Technology, Shinshu University, Ueda 386-8567, JapanResearch Initiative for Supra-Materials (RISM), Shinshu University, Ueda 386-8567, JapanThe utilization of dodecaborate boron clusters, [B<sub>12</sub>X<sub>12</sub>]<sup>2−</sup> (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkylation of [B<sub>12</sub>Br<sub>11</sub>OH]<sup>2−</sup> to functionalize it with an aliphatic spacer was developed with a view to expanding the known chemical space of membrane carriers based on [B<sub>12</sub>Br<sub>12</sub>]<sup>2−</sup>. A new and improved facile route for the preparation of [B<sub>12</sub>Br<sub>11</sub>OH]<sup>2−</sup>, which is an important precursor to other [B<sub>12</sub>Br<sub>11</sub>OR]<sup>2−</sup> species, is reported. Various alkoxylated [B<sub>12</sub>Br<sub>11</sub>O(CH<sub>2</sub>)<sub>5</sub>Z]<sup>2−</sup> (Z = OH, N(CO)<sub>2</sub>C<sub>6</sub>H<sub>4</sub>, CN and N<sub>3</sub>) derivatives were prepared via a divergent synthesis based on [B<sub>12</sub>Br<sub>11</sub>O(CH<sub>2</sub>)<sub>5</sub>Br]<sup>2−</sup>. One of the newly synthesized compounds was utilized as a membrane carrier, and its impact on cell viability was examined.https://www.mdpi.com/2624-8549/6/6/99boron clusterchaotropicmembrane transport |
| spellingShingle | Satoshi Yamamoto Hibiki Nakamura Yumiko K. Kawamura Taro Kitazawa Mutsumi Kimura Yu Kitazawa Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers Chemistry boron cluster chaotropic membrane transport |
| title | Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers |
| title_full | Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers |
| title_fullStr | Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers |
| title_full_unstemmed | Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers |
| title_short | Alkoxy Substituted Brominated <i>closo</i>-Dodecaborates with Functionalized Aliphatic Spacers |
| title_sort | alkoxy substituted brominated i closo i dodecaborates with functionalized aliphatic spacers |
| topic | boron cluster chaotropic membrane transport |
| url | https://www.mdpi.com/2624-8549/6/6/99 |
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