Enhanced N-directed electrophilic C–H borylation generates BN–[5]- and [6]helicenes with improved photophysical properties
| العنوان: | Enhanced N-directed electrophilic C–H borylation generates BN–[5]- and [6]helicenes with improved photophysical properties |
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| المؤلفون: | Agnieszka Nowak-Król, Michael J. Ingleson, Gary S. Nichol, Daniel Volland, Marina Uzelac, Sven Kirschner, Kang Yuan |
| المصدر: | Yuan, K, Volland, D, Kirschner, S, Uzelac, M, Nichol, G S, Nowak-krol, A & Ingleson, M J 2022, ' Enhanced N-directed electrophilic C-H borylation generates BN-[5]-and [6]helicenes with improved photophysical properties. ', Chemical Science . https://doi.org/10.1039/D1SC06513K Chemical Science |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2022. |
| سنة النشر: | 2022 |
| مصطلحات موضوعية: | chemistry.chemical_compound, Helicene, chemistry, Stereochemistry, Electrophile, Helix, Enantioselective synthesis, Supramolecular chemistry, Protonation, General Chemistry, Racemization, Borylation |
| الوصف: | Helicenes are chiral polycyclic aromatic hydrocarbons (PAHs) of significant interest e.g. in supramolecular chemistry, materials science and asymmetric catalysis. Herein an enhanced N-directed electrophilic C-H borylation methodology has been developed that provides access to azaborine containing helicenes (BN-helicenes). This borylation process proceeds via protonation of an aminoborane with bistriflimidic acid. DFT calculations reveal the borenium cation formed by protonation to be more electrophilic than the product derived from aminoborane activation with BBr3. The synthesised helicenes include BN-analogues of archetypal all carbon [5]- and [6]helicenes. The replacement of a CC with a BN unit (that has a longer bond) on the outer helix increases the strain in the BN congeners and the racemization half-life for a BN-[5]helicene relative to the all carbon [5]helicene. BN incorporation also increases the fluorescence efficency of the helicenes, a direct effect of BN incorporation altering the distribution of the key frontier orbitals across the helical backbone relative to carbo-helicenes. |
| وصف الملف: | application/pdf |
| تدمد: | 2041-6539 2041-6520 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::397675aecbf738794c2f60d0489b79e2 https://doi.org/10.1039/d1sc06513k |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....397675aecbf738794c2f60d0489b79e2 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 20416539 20416520 |
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