Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Department of Chemical and Biomolecular Engineering, University of California , Los Angeles, California 90095, United States.
J Am Chem Soc. 2017 Aug 2;139(30):10447-10455. doi: 10.1021/jacs.7b05317. Epub 2017 Jul 18.
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.
我们报告了一类新型吲哚基共轭三聚体的设计和合成。目标化合物是通过 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获得的。通过利用三种吲哚啉异构体，可以获得六种异构吲哚三聚体，其中没有一种以前被合成过。使用计算分析，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应用，同时提供了一类新的共轭三聚体，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性存在差异，但每个三聚体的光物理性质都来源于 N-甲基吲哚砌块。激发态行为遵循可预测的模式。
