C-C cross-coupling reactions for the combinatorial synthesis of novel organic materials
C-C cross-coupling reactions for the combinatorial synthesis of novel organic materials
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DOI：
10.1016/s0022-328x(02)01153-1
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发表时间：
2002-07-01
影响因子：
2.3
通讯作者：
Bauerle, P
中科院分区：
文献类型：
--
作者：
Schiedel, MS;Briehn, CA;Bauerle, P
为了加快有机材料的开发进程，香豆素类染料和低聚硫吩类化合物的组合策略和筛选方法已经有了代表性的阐述。采用Pd催化的铃木、Sonogashira-Hagihara和Heck类型的交叉偶联取代香豆素支架。优化的合成方案被应用于以并行方式在溶液中构建150多个香豆素衍生物的不同文库。为了评价荧光分子系，对香豆素类化合物的光学性质进行了筛选，并确定了几个具有高荧光量子产率的文库成员。在固相合成的基础上，采用平行和混合分裂两种方法，构建了一个256元的3-芳基噻吩季铵盐S文库。采用Suzuki型偶联剂，以不同芳基取代的噻吩型硼酸酯为基块，逐步生长低聚物。电化学性质的快速筛选是通过使用自动筛选设备实现的。数据分析导致了结构-性能关系的发展，作为未来材料设计的基础。(C)2002 Elsevier Science B.V.保留所有权利。
To accelerate the development process to organic materials combinatorial strategies and screening methodologies have been representatively elaborated for coumarin dyes and oligothiophenes. Pd-catalyzed cross-couplings of Suzuki, Sonogashira-Hagihara and Heck type were utilized to substitute the coumarin scaffold. Optimized synthetic protocols were applied to construct in a parallel manner in solution diverse libraries of more than 150 coumarin derivatives. To evaluate the fluorophore ensemble, the coumarins were screened for optical properties and several library members with high fluorescence quantum yields were identified. Using solid-phase synthesis, a 256-membered library of quater(3-arylthiophene)s was generated by using both the parallel and the 'mix-and-split' technique. Suzuki type couplings were employed for the stepwise oligomer growth using diverse aryl substituted thiophene boronic esters as building blocks. The rapid screening for electrochemical properties was facilitated by using an automated screening device. The data analysis led to the development of structure-property relationships on which to base future material design. (C) 2002 Elsevier Science B.V. All rights reserved.