Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain.
Org Lett. 2013 Sep 6;15(17):4454-7. doi: 10.1021/ol401993p. Epub 2013 Aug 12.
New 8-alkenylBODIPYs have been synthesized by Knoevenagel condensation between a series of alkyl-substituted-3,8-dimethylBODIPYs and aromatic or aliphatic aldehydes. This is in clear contrast with literature precedents, which indicate that this reaction occurs exclusively on the methyl group at C-3. The change in hybridization of the carbon at the 8-position (from sp(3) to sp(2)) determines the fluorescence emission of the BODIPY, while the presence of electron-donating or -withdrawing groups leads to intramolecular charge transfer processes.
新型 8-烯基 BODIPY 通过一系列烷基取代的 3,8-二甲基 BODIPY 与芳香族或脂肪族醛之间的 Knoevenagel 缩合反应合成。这与文献先例形成鲜明对比，文献先例表明该反应仅发生在 C-3 上的甲基上。8 位碳的杂化状态（从 sp(3) 变为 sp(2)）的变化决定了 BODIPY 的荧光发射，而供电子或吸电子基团的存在则导致分子内电荷转移过程。
