Direct Phenylation of nido-B10H14

0559702 - ÚACH 2023 RIV US eng J - Článek v odborném periodiku
Demel, Jan - Kloda, Matouš - Lang, Kamil - Škoch, Karel - Hynek, Jan - Opravil, Adam - Novotný, Matyáš - Bould, Jonathan - Ehn, Marcel - Londesborough, Michael Geoffrey Stephen
Direct Phenylation of nido-B10H14.
Journal of Organic Chemistry. Roč. 87, č. 15 (2022), s. 10034-10043. ISSN 0022-3263. E-ISSN 1520-6904
Grant CEP: GA ČR(CZ) GA18-20286S; GA MŠMT(CZ) LM2018124
Institucionální podpora: RVO:61388980
Klíčová slova: Aromatic compounds * Cluster chemistry * Fluorescence * Group 13 compounds * Hydrocarbons
Obor OECD: Inorganic and nuclear chemistry
Impakt faktor: 3.6, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1021/acs.joc.2c00997

As a preliminary step toward its condensation into the porous polymer Activated Borane, the thermolysis of nido-B10H14 (1) in benzene at 200 ? results in the generation of a number of phenylated borane molecular species. The principal product is the new mono-phenylated compound 5-Ph-nido-B10H14 (2), isolated in 48% yield (based on consumption of 1) and structurally characterized by single-crystal X-ray diffraction analysis, NMR, and mass spectrometry along with other minor products, such as 6-Ph-nido-B10H13 (3), for which we observe UV-light-driven conversion into 2 via a ´vertex-flip ´ mechanism, and novel diphenylated 5,8-Ph2-nido-B10H12 (4). Together, the phenylated derivatives provide a valuable insight into the assembly of Activated Borane and ultimately inform on its structure. The new compounds also display strong blue fluorescence in both solid-state and in solution and are the first examples of the direct phenylation of nido-B10H14 , thus opening the door to the straight-forward synthesis of highly luminescent organic-borane hybrid systems.
Trvalý link: https://hdl.handle.net/11104/0332920


Vědecká data: CCDC, CCDC