Dissymmetrical Chiral Peropyrenes: Synthesis via Iridium-Catalyzed C-H Activation/Alkyne Benzannulation and Study of Their Properties

被引：2

作者：

George, Stephen P. ^{[1
]}

Spengler, Jonas ^{[2
,3
]}

Malone, Ryan J. ^{[4
]}

Krzoska, James ^{[4
]}

Wuerthner, Frank ^{[2
,3
]}

Chalifoux, Wesley A. ^{[4
,5
]}

机构：

[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA

[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[3] Univ Wurzburg, Ctr Nanosyst Chem CNC, D-97074 Wurzburg, Germany

[4] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

[5] Univ Alberta, Dept Chem, 11227 Saskatchewan Dr, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 07期

基金：

美国国家科学基金会;

关键词：

PHOTOPHYSICAL PROPERTIES; PYRENE; NANOGRAPHENES;

D O I：

10.1021/acs.joc.3c02985

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dissymmetrical chiral peropyrenes with electron-rich and electron-deficient aryl substituents in the bay regions were synthesized via iridium-catalyzed C-H activation and alkyne benzannulation. The electronic properties were studied using cyclic and differential pulse voltammetry. The enantiomers were separated and exhibited high g(lum) and g(abs) values in circularly polarized luminescence (CPL) and circular dichroism (CD), respectively. Variable-temperature NMR experiments were conducted on symmetrical and dissymmetrical chiral peropyrenes to compare the barrier to rotation of the aryl groups in the bay region.

引用

页码：5159 / 5163

页数：5

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