Modular Synthesis of Rigid Polyacene Dimers for Singlet Fission
Modular Synthesis of Rigid Polyacene Dimers for Singlet Fission
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DOI：
10.1021/acs.orglett.7b03817
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发表时间：
2018-01-19
期刊：
影响因子：
5.2
通讯作者：
Damrauer, Niels H.
中科院分区：
文献类型：
--
作者：
Carey, Thomas J.;Miller, Ethan G.;Damrauer, Niels H.
一个改进的，模块化合成刚性，几何上明确定义，炔取代四烯(1)和并戊烯(2)二聚体报道。该合成是由降冰片基四烯与三异丙基硅基乙炔取代（tips -乙炔）醌亲二烯试剂的连续Diels-Alder反应合成的。在合成早期加入增溶和稳定的tips -乙炔基团提供了一条温和可靠的途径，首次为降冰片烯桥接的五苯二聚体提供了途径。还描述了这些分子的激发态行为的初步探索。
An improved, modular synthesis of rigid, geometrically well-defined, alkyne-substituted tetracene (1) and pentacene (2) dimers is reported. The synthesis is rooted in sequential Diels-Alder reactions of a norbornyl tetraene with triisopropylsilylacetylene-substituted (TIPS-acetylene) quinone dienophiles. The incorporation of solubilizing and stabilizing TIPS-acetylene groups early in the synthesis affords a mild and reliable route, providing access, for the first time, to norbornyl-bridged pentacene dimers. A preliminary exploration of the excited state behavior of these molecules is also described.