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

共 50 条

[41] Iridium(III)-Catalyzed Synthesis of Benzimidazoles via C-H Activation and Amidation of Aniline Derivatives
Xia, Jintao
Yang, Xifa
Li, Yunyun
Li, Xingwei
ORGANIC LETTERS, 2017, 19 (12) : 3243 - 3246
[42] Iridium-Catalyzed Enantioselective Hydroarylation of Alkenes through C-H bond Activation: Experiment and Computation
Shinde, Valmik S.
Mane, Manoj V.
Cavallo, Luigi
Rueping, Magnus
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (37) : 8308 - 8313
[43] Iridium-Catalyzed Sequential Silylation and Borylation of Heteroarenes Based on Regioselective C-H Bond Activation
Murai, Masahito
Nishinaka, Naoki
Takai, Kazuhiko
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (20) : 5843 - 5847
[44] Highly Flexible Synthesis of Chiral Azacycles via Iridium-Catalyzed Hydrogenation
Verendel, J. Johan
Zhou, Taigang
Li, Jia-Qi
Paptchikhine, Alexander
Lebedev, Oleg
Andersson, Pher G.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8880 - +
[45] Coupling of alkylarene and pentamethyl[60]fullerene by iridium-catalyzed benzylic C-H bond activation
Matsuo, Yutaka
Iwashita, Akihiko
Nakamura, Eiichi
CHEMISTRY LETTERS, 2006, 35 (08) : 858 - 859
[46] Synthesis of Chiral Hydantoins and Thiazolidinediones via Iridium-Catalyzed Asymmetric Hydrogenation
Nie, Yu
Li, Jing
Yuan, Qianjia
Zhang, Wanbin
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (07) : 819 - 824
[47] Efficient synthesis of chiral β-hydroxy sulfones via iridium-catalyzed hydrogenation
Tao, Lin
Yin, Congcong
Dong, Xiu-Qin
Zhang, Xumu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (04) : 785 - 788
[48] Iridium-Catalyzed Electrooxidative Annulation of Naphthol with Acrylate via C-H Bond Activation for the Synthesis of Naphtho[1,8-bc]furan
Patil, Nilam
Das, Debarati
Bhanage, Bhalchandra M.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (26)
[49] Theoretical study on the mechanism of iridium-catalyzed γ-functionalization of primary alkyl C-H bonds
Li, Zhe
Xia, Miaoren
Boyd, Russell J.
CANADIAN JOURNAL OF CHEMISTRY, 2016, 94 (12) : 1028 - 1037
[50] Iridium-Catalyzed Borylation of Secondary C-H Bonds in Cyclic Ethers
Liskey, Carl W.
Hartwig, John F.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12422 - 12425

← 1 2 3 4 5 →