Synthesis of Monodisperse Oligo(1,4-phenyleneethynylene-alt-1,4-triptycyleneethynylene)s
作者:Daniela Maag、Tilman Kottke、Miriam Schulte、Adelheid Godt
DOI:10.1021/jo9009744
日期:2009.10.16
The synthesis of monodisperse oligo(p-phenyleneethynylene)s 8an with alternating 2,5-dihexyl-1,4-phenylene and 6,14-di-tert-butyl-1,4-triptycylene units and orthogonally protected alkyne end groups is reported. Starting from 6,14-di-tert-butyl-1-(2-triisopropylsilylethynyl)-4-(2-trimethylsilylethynyl)triptycene (5a), 1,4-dihexyl-2,5-diiodobenzene (10), and 1,4-dihexyl-2-iodo-5-(3-hydroxyprop-1-ynyl)benzene
单分散低聚(合成p -phenyleneethynylene)类8A Ñ具有交替的2,5-二己基-1,4-亚苯基和-6,14-二-叔-丁基-1,4- triptycylene单元和正交保护的炔端基是报告。从6,14-二叔丁基-1-(2-三异丙基甲硅烷基乙炔基)-4-(2-三甲基甲硅烷基乙炔基)三茂烯(5a),1,4-二己基-2,5-二碘苯(10)和1, 4-二己基-2-碘-5-(3-羟基丙-1-炔基)苯(9),通过以炔基-芳基(Sonogashira-Hagihara)偶联为关键反应的部分发散-收敛路线,制备了具有最多四个重复单元(即八个亚苯基亚乙炔基单元)的低聚物。由三苯并二苯醌通过添加2-三烷基甲硅烷基乙炔基锂,还原和同时消除水,将苯酚转化成三氟甲磺酸酯,以及最后由Pd / Cu催化的与三烷基甲硅烷基乙炔的偶联来制备起始化合物5a。严格的发散-收敛途径对关键化合物的相似途径是6,14-