Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
Institute of Physical Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 2, 76131, Karlsruhe, Germany.
Chemistry. 2019 Mar 12;25(15):3816-3827. doi: 10.1002/chem.201806330. Epub 2019 Feb 27.
Dipyrromethene metal complexes are fascinating molecules that have applications as light-harvesting systems, luminophores, and laser dyes. Recently, it has been shown that structurally rigid bis(dipyrrinato) zinc(II) complexes exhibit high fluorescence with comparable quantum yields to those of boron dipyrromethenes or BODIPYs. Herein, eight new bis(dipyrrinato) Zn complexes, obtained from symmetric and unsymmetrical functionalization of the dipyrromethene structure through a Knoevenagel reaction, are reported. It was possible not only to vary the maximum visible absorption from 490 to 630 nm, but also to enhance the emission quantum yield up to 66 %, which is extraordinarily high for homoleptic bis(dipyrrinato) zinc complexes. These results pave the way for designing highly luminescent bis(dipyrrinato) zinc complexes.
二吡咯并甲川金属配合物是一类引人入胜的分子，在光捕获系统、荧光团和激光染料方面具有应用。最近表明，结构刚性的双（二吡咯甲川）锌（II）配合物具有高荧光，其量子产率可与硼二吡咯甲川或 BODIPY 相媲美。在此，通过 Knoevenagel 反应对二吡咯并甲川结构进行对称和非对称官能化，得到了 8 种新的双（二吡咯甲川）Zn 配合物。不仅可以将最大可见吸收从 490nm 变化到 630nm，而且还可以将发射量子产率提高到 66%，对于同配位的双（二吡咯甲川）锌配合物来说，这是非常高的。这些结果为设计高发光双（二吡咯甲川）锌配合物铺平了道路。
