Qiu Shuxian, Dong Duan, Li Jiahui, Wen Huiting, Li Jinpeng, Yang Yu, Zhai Shengxian, Gao Xingyuan
College of Chemistry and Material Science, Guangdong University of Education, Guangzhou 510303, China.
College of Chemistry and Chemical Engineering, Tarim University, Aral City 843300, China.
Beilstein J Org Chem. 2024 Dec 30;20:3299-3305. doi: 10.3762/bjoc.20.274. eCollection 2024.
A novel series of D-A-D-type 9-phenyl-9-phosphafluorene oxide (PhFlOP) derivatives was prepared and is reported herein. The synthetic protocol involved 5 steps from commercially available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield, especially for the final CsCO-facilitated nucleophilic substitution (77-91% yield). The characterization data obtained from IR and NMR spectroscopy (H, C, F, and P) as well as HRMS spectrometry were in full agreement with the expected structures, and single-crystal X-ray diffraction analysis was conducted to confirm the structure of compound . Moreover, the photophysical properties of these PhFlOP derivatives were determined by UV-vis absorption and photoluminescence studies, revealing that their photophysical behavior can be affected by the different substituents in the donor carbazole group.
本文制备并报道了一系列新型的D-A-D型9-苯基-9-氧化磷芴（PhFlOP）衍生物。合成方案从市售的2-溴-4-氟-1-硝基苯开始，共五步，具有无贵金属体系、反应条件温和、产率良好的特点，特别是对于最后的碳酸铯促进的亲核取代反应（产率77-91%）。通过红外光谱和核磁共振光谱（H、C、F和P）以及高分辨质谱获得的表征数据与预期结构完全一致，并进行了单晶X射线衍射分析以确认化合物的结构。此外，通过紫外可见吸收和光致发光研究确定了这些PhFlOP衍生物的光物理性质，结果表明它们的光物理行为会受到供体咔唑基团中不同取代基的影响。
