Dithiophene‐Fused Oxadiborepins and Azadiborepins: A New Class of Highly Fluorescent Heteroaromatics
| Autor: | Andreas Helbig, Holger Helten, Jonas Bachmann, Ivo Krummenacher, Merian Crumbach, Holger Braunschweig, Lars Fritze |
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| Rok vydání: | 2021 |
| Předmět: |
Materials science
polycycles chemistry.chemical_element isoelectronic analogues 010402 general chemistry Ring (chemistry) Photochemistry 01 natural sciences Catalysis BN compounds Anisotropy Boron Quantum 010405 organic chemistry Communication π‐Conjugated Molecules | Hot Paper Aromaticity General Medicine aromaticity General Chemistry Fluorescence Communications 0104 chemical sciences chemistry ddc:540 Cyclic voltammetry boron Current density |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202100295 |
| Popis: | Access to dithiophene‐fused oxadiborepins and the first azadiborepins attained via a modular synthesis route are presented. The new compounds emit intense blue light, some of which demonstrate fluorescence quantum yields close to unity. Cyclic voltammetry (CV) revealed electrochemically reversible one‐electron reduction processes. The weak aromatic character of the novel 1,2,7‐azadiborepin ring is demonstrated with in‐depth theoretical investigations using nucleus‐independent chemical shift (NICS) scans and anisotropy of the induced current density (ACID) calculations. Dithienooxa‐ and ‐azadiborepins are accessible in a modular way from a common precursor. These BNB‐doped polycyclic aromatic hydrocarbons (PAHs) are highly efficient blue‐light emitters with quantum yields up to 96 %. In‐depth theoretical studies reveal that the previously unknown azadiborepin ring system is weakly aromatic. |
| Databáze: | OpenAIRE |
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