Synthesis of Monodisperse Oligo(para‐phenyleneethynylene)s Using Orthogonal Protecting Groups with Different Polarity for Terminal Acetylene Units
Synthesis of Monodisperse Oligo(para‐phenyleneethynylene)s Using Orthogonal Protecting Groups with Different Polarity for Terminal Acetylene Units
复制标题
利用末端乙炔单元不同极性的正交保护基合成单分散低聚（对亚苯基乙炔基）
DOI：
--
复制
发表时间：
1999
期刊：
影响因子：
--
通讯作者：
A. Godt
中科院分区：
文献类型：
--
作者：
Hildegard Kukula;S. Veit;A. Godt
以1，4-二己基-2-（3-羟基丙-1-炔基）-5-[2-（三异丙基硅基）乙炔基]苯为起始原料，采用Pd/Cu催化的炔-芳基偶联反应，通过发散-收敛法合成了单分散的低聚（对苯乙炔基）（oligopepes）。基团羟甲基（HOM）和三异丙基甲硅烷基（TIPS）用作乙炔部分的正交保护基团。极性HOM基团对产物的色谱行为有很强的影响，使纯化合物的分离非常容易。合成一直进行到九聚体。oligopPEs进行了充分的表征，包括吸收和发射光谱数据。
Monodisperse oligo(para-phenyleneethynylene)s (oligoPPEs) were synthesized by a divergent-convergent synthesis starting from 1,4-dihexyl-2-(3-hydroxyprop-1-ynyl)-5-[2-(triisopropylsilyl)ethynyl]benzene and using the Pd/Cu-catalyzed alkyne-aryl coupling. The groups hydroxymethyl (HOM) and triisopropylsilyl (TIPS) function as orthogonal protective groups for the acetylene moieties. The polar HOM group shows a strong impact on the chromatographic behaviour of the products and makes the isolation of pure compounds very easy. The synthesis was pursued up to the nonamer. The oligoPPEs were fully characterised, including absorption and emission spectral data.