核心氟化BODIPY-3,5-二酰胺的高效合成
Efficient Synthesis of Core-Fluorinated BODIPY-3,5-Diamides.
作者信息
Shambalova Victoria E, Mikheeva Sofiya R, Aldoshin Alexander S, Moiseeva Anna A, Safonova Evgeniya A, Gorbunova Yulia G, Nenajdenko Valentine G
机构信息
Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Building 3, Moscow 119991, Russia.
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr., 31, Building 4, Moscow 119071, Russia.
出版信息
Int J Mol Sci. 2025 May 8;26(10):4484. doi: 10.3390/ijms26104484.
A modular synthesis of a new family of core-fluorinated BODIPYs was elaborated. -Fluoro--nitrostyrenes were used as starting materials to prepare a set of mono-fluorinated pyrrole-2-amides using the Barton-Zard reaction with 2-isocyanoacetamides. The prepared monofluorinated building blocks were successively transformed into the corresponding dipyrromethanes and 1,7-difluoro-BODIPY-3,5-diamides. As a result, a new family of luminophores with a combination of fluorescence and photosensitizing properties was obtained. The photophysical properties of novel BODIPYs were studied by UV-vis and fluorescence spectroscopy, cyclic voltammetry and DFT calculations. In addition, their ability to generate singlet oxygen was assessed. The properties of 1,7-difluoro-BODIPY-3,5-diamides were compared with their analogues to reveal the substituent effect at the 3,5-positions. The fluorescent properties of the obtained dyes were significantly improved in comparison to their 3,5-diester analogous.
阐述了一种新型核心氟化BODIPY家族的模块化合成方法。使用氟代硝基苯乙烯作为起始原料，通过与2-异氰基乙酰胺的巴顿-扎德反应制备了一组单氟代吡咯-2-酰胺。将制备的单氟代结构单元依次转化为相应的二吡咯甲烷和1,7-二氟-BODIPY-3,5-二酰胺。结果，获得了一个具有荧光和光敏特性组合的新型发光体家族。通过紫外-可见光谱、荧光光谱、循环伏安法和密度泛函理论计算研究了新型BODIPY的光物理性质。此外，评估了它们产生单线态氧的能力。将1,7-二氟-BODIPY-3,5-二酰胺的性质与其类似物进行比较，以揭示3,5-位的取代基效应。与它们的3,5-二酯类似物相比，所得染料的荧光性质得到了显著改善。
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