Synthesis, Structures, and Electronic Properties of 2,7-Anthrylene-Based Azacyclophanes Bearing o-, m-, and p-Phenylenediamine Linkers

被引：3

作者：

Iwanaga, Tetsuo ^{[1
]}

Komori, Takashi ^{[1
]}

Sato, Hiroki ^{[1
]}

Suzuki, Shuichi ^{[2
]}

Yamauchi, Tomokazu ^{[3
]}

Misaki, Yohji ^{[3
]}

Sato, Hiroyasu ^{[4
]}

Toyota, Shinji ^{[5
]}

机构：

[1] Okayama Univ Sci, Fac Sci, Dept Chem, Okayama 7000005, Japan

[2] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Toyonaka, Osaka 5608531, Japan

[3] Ehime Univ, Grad Sch Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan

[4] Rigaku Corp, Xray Res Lab, Akishima, Tokyo 1968666, Japan

[5] Tokyo Inst Technol, Sch Sci, Dept Chem, Meguro Ku, Tokyo 1528551, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期

关键词：

RADICAL CATIONS; BIS(TRIARYLAMINE) DICATIONS; DELOCALIZATION; OLIGOMERS; THIELES; ANALOGS; SINGLET; BOND;

D O I：

10.1021/acs.joc.1c00856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel azacyclophanes consisting of 2,7-anthrylene and phenylene units were designed and synthesized by the Buchwald-Hartwig coupling reaction to investigate their unique electronic properties in multiple oxidized states. Cyclic voltammetry showed that the p-phenylene derivative exhibited three reversible oxidation waves, whereas the o- and m-phenylene derivatives showed two quasi-reversible oxidation waves due to the complicated intramolecular interaction between the oxidized units and neutral units. Moreover, the absorption spectra of the p-phenylene derivative in different oxidation states showed absorption bands at 865 and 1025 nm, which were attributed to intramolecular chargetransfer interactions. The photophysical and electrochemical properties of the p-phenylene analog were also compared with those of the o- and m-phenylene derivatives based on theoretical calculations for further evaluation of the intramolecular electronic interactions.

引用

页码：11370 / 11377

页数：8

共 42 条

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