区域选择性合成 5-单取代苯乙烯基和 2-四氰基丁二烯 BODIPY 染料。
Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes.
机构信息
LCOSA, UMR7515, CNRS/Université de Strasbourg/ECPM, 25 rue Becquerel, 67087 Strasbourg, Cedex 02, France.
出版信息
Org Lett. 2011 Oct 7;13(19):4996-9. doi: 10.1021/ol201600s. Epub 2011 Sep 8.
Several unsymmetrically 2,5-disubstituted BODIPY dyes were obtained from 2-substituted derivatives (iodo, ethynylaryl) using a regioselective Knoevenagel condensation reaction with dimethylaminobenzaldehyde. The unsaturated, unsymmetrical 2-ethynyl-5-styryl-BODIPY undergoes a regioselective [2 + 2] cycloaddition reaction with tetracyanoethylene leading to the 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivative. This shows rich redox activity with two reversible oxidation and three reversible reduction waves at +0.72 V, +1.04 V; -0.32 V, -0.78 V, and -1.50 V, respectively.
几种不对称的 2,5-取代 BODIPY 染料是通过 2-取代衍生物（碘代、炔基芳基）与二甲氨基苯甲醛的区域选择性 Knoevenagel 缩合反应得到的。不饱和、不对称的 2-乙炔基-5-苯乙烯基-BODIPY 与四氰乙烯发生区域选择性 [2 + 2]环加成反应，生成 1,1,4,4-四氰基丁-1,3-二烯（TCBD）衍生物。该衍生物具有丰富的氧化还原活性，在 +0.72 V、+1.04 V 处有两个可逆氧化峰和三个可逆还原峰，分别为 -0.32 V、-0.78 V 和 -1.50 V。
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