Modular Synthesis of Rigid Polyacene Dimers for Singlet Fission

被引：25

作者：

Carey, Thomas J. ^{[1
]}

Miller, Ethan G. ^{[1
]}

Gilligan, Alexander T. ^{[1
]}

Sammakia, Tarek ^{[1
]}

Damrauer, Niels H. ^{[1
]}

机构：

[1] Univ Colorado Boulder, Dept Chem & Biochem, Boulder, CO 80309 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 02期

基金：

美国国家科学基金会;

关键词：

CHARGE-TRANSFER; EXCITON FISSION; STATES; EXPLORATION;

D O I：

10.1021/acs.orglett.7b03817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：457 / 460

页数：4

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