Conjugated Trimeric Scaffolds Accessible from Indolyne Cyclotrimerizations: Synthesis, Structures, and Electronic Properties
Conjugated Trimeric Scaffolds Accessible from Indolyne Cyclotrimerizations: Synthesis, Structures, and Electronic Properties
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DOI：
10.1021/jacs.7b05317
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发表时间：
2017-08-02
影响因子：
15
通讯作者：
Houk, K. N.
中科院分区：
文献类型：
--
作者：
Lin, Janice B.;Shah, Tejas K.;Houk, K. N.
我们报告了一类新型吲哚基共轭三聚体的设计和合成。使用 Pd 催化的环三聚反应，从原位生成的高反应性吲哚啉中间体中获得目标化合物。通过利用三种吲哚炔异构体，可以获得六种异构吲哚三聚体，其中没有一种是以前合成的。通过计算分析，我们描述了这些独特化合物的结构和光物理性质。这项研究展示了吲哚啉在过渡金属催化反应中的用途，同时提供了获得一类新型共轭三聚体的途径，包括高度弯曲的杂芳族化合物。计算表明，尽管分子之间的平面度存在差异，但每个三聚体的光物理性质均源自 N-甲基吲哚结构单元。兴奋状态行为遵循可预测的模式。
We report the design and synthesis of a new class of indole-based conjugated trimers. The targeted compounds are accessed from in situ generated, highly reactive indolyne intermediates using Pd-catalyzed cyclotrimerization reactions. By harnessing three indolyne isomers, six isomeric indole trimers are accessible, none of which have been previously synthesized. Using computational analysis, we describe the structural and photophysical properties of these unique compounds. This study showcases the use of indolynes in transition metal-catalyzed reactions, while providing access to a new class of conjugated trimers, including highly bent heteroaromatic compounds. Computations indicate that, despite differences in planarity between the molecules, the photophysical properties of each trimer are derived from the N-methylindole building block. Excited state behavior follows predicable patterns.