Wüst Leonie, Chorbacher Johannes, Keim Timo, Wellnitz Tim, Spieß Julian, Wieprecht Nele, Michel Maximilian, Helten Holger, Braunschweig Holger
Julius-Maximilians-Universität Würzburg, Institute of Inorganic Chemistry Am Hubland 97074 Würzburg Germany
Institute for Sustainable Chemistry & Catalysis with Boron Am Hubland 97074 Würzburg Germany.
Chem Sci. 2025 Jun 30. doi: 10.1039/d5sc03814f.
B-Aryl-based 1,2,3-diazaborinates (DABates), derived from neutral 1,2,3-diazaborines (DABs), are a promising class of unexplored fluorophores which show an intriguing high optical performance. This work systematically investigates previously unexplored factors that govern their photoluminescence. We strategically designed and synthesized a diverse library of DABate derivatives, modifying the exocyclic boron and N-substituents, the N-lone pair, and the fused π system. All compounds were fully characterized by conventional NMR, HRMS and XRD techniques, as well as UV-vis and fluorescence spectroscopy. Our results allow the identification of key molecular attributes which enhance or quench the fluorescence. Complementary supporting time-dependent DFT calculations provide further insights into the excitation process. In addition, we also performed modifications to render the DABates air- and moisture-stable, expanding potential future applications of this novel class of potent fluorophores beyond inert conditions.
基于芳基的1,2,3-重氮硼酸盐（DABates）由中性1,2,3-重氮硼烷（DABs）衍生而来，是一类有前途但尚未探索的荧光团，具有引人注目的高光性能。这项工作系统地研究了以前未探索的影响其光致发光的因素。我们精心设计并合成了一系列多样的DABate衍生物库，对环外硼和N-取代基、N-孤对电子以及稠合π体系进行了修饰。所有化合物均通过常规核磁共振、高分辨质谱和X射线衍射技术以及紫外可见光谱和荧光光谱进行了全面表征。我们的结果能够确定增强或淬灭荧光的关键分子属性。互补的含时密度泛函理论计算为激发过程提供了进一步的见解。此外，我们还进行了修饰以使DABates对空气和水分稳定，从而将这类新型高效荧光团的潜在未来应用扩展到惰性条件之外。
