Department of Food Engineering, Bingöl University, Bingöl, 12000, Turkey.
Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.
Chem Commun (Camb). 2022 Jun 23;58(51):7188-7191. doi: 10.1039/d2cc02179j.
We report a boron dipyrromethene that is chiral at boron and carbon (BC-BODIPY) and accessible through a two-pot, one-step synthesis-an interrupted Knoevenagel condensation. The electronic circular dichroism spectra of chiral high performance liquid chromatography-resolved enantiomers show clear Cotton effects (∣∣ ∼ 2.0 × 10) in the visible region, suggesting efficient chirality induction to the otherwise achiral BODIPY. The dye's unusually weak fluorescence ( < 0.01) is attributed partly to vibrational relaxations, as revealed by viscosity experiments, and partly to probable intersystem crossing that may be facilitated by the reduced symmetry of the bent-shaped molecular geometry.
我们报告了一种手性硼二吡咯甲川（BC-BODIPY），它可以通过两步一锅法合成——一种中断的 Knoevenagel 缩合反应来制备。手性高效液相色谱拆分的对映异构体的电子圆二色光谱在可见区显示出明显的（∣∣ ∼ 2.0 × 10）Cotton 效应，表明对原本无手性的 BODIPY 具有有效的手性诱导。该染料的荧光非常弱（ < 0.01），部分归因于振动弛豫，这可以通过粘度实验来揭示，部分归因于可能的系间窜越，这可能是由弯曲分子几何形状的对称性降低所促进的。
