Amine-Amine Electronic Coupling through an Anthracene Bridge

doi:10.6023/cjoc201606020

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2407-2412.DOI: 10.6023/cjoc201606020 Previous Articles Next Articles

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蒽桥联的胺-胺电子耦合研究

冯骏^a,b, 邵将洋^a, 龚忠亮^a, 钟羽武^a,b

a 中国科学院化学研究所北京 100190;
b 中国科学院大学北京 100149

收稿日期:2016-06-13 修回日期:2016-07-17 发布日期:2016-08-10
通讯作者: 钟羽武,E-mail:zhongyuwu@iccas.ac.cn E-mail:zhongyuwu@iccas.ac.cn
基金资助:
国家自然科学基金（Nos.21271176，21472196，21521062，21501183）和中国科学院战略性先导科技专项（No.XDB12010400）资助项目

Amine-Amine Electronic Coupling through an Anthracene Bridge

Feng JunShao^a,b, Jiangyang^a, Gong Zhongliang^a, Zhong Yuwu^a,b

a Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2016-06-13 Revised:2016-07-17 Published:2016-08-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21271176, 21472196, 21521062, 21501183), and the Strategic Priority Research Program of the Chinese Academy of Sciences (No.XDB12010400).

1. Amine-Amine Electronic Coupling through an Anthracene Bridge.PDF(874KB)

Abstract

Three diamine compounds with an anthracene bridge were synthesized and characterized, including 1,5-bis(di-p-anisylamine)anthracene (1), 2,6-bis(di-p-anisylamine)anthracene (2) and 9,10-bis(di-p-anisylamine)anthracene (3). The elec-trochemistry, absorption and emission spectra, spectroelectrochemistry, and amine-amine electronic coupling of these compounds were examined. All compounds display two consecutive redox couples in the potential region between +0.6 and +1.0 V vs Ag/AgCl, with a potential splitting △E of around 100 mV. In the one-electron-oxidized state, weak intervalence charge transfer (IVCT) transitions were observed for 1^·+ in the near-infrared (NIR) region and the electronic coupling parameter V_ab was calculated to be 600 cm^-1. In contrast, compound 3^·+ displays an intense IVCT band in the NIR region with a V_ab value of 1440 cm^-1. However, no distinct IVCT band was discernable for 2^·+, indicative of an eligible electronic coupling. This work demonstrates that the positions of the amine substituents on the anthracene bridge play a critical role in determining the degree of amine-amine electronic coupling.

Key words: amines, charge transfer, electrochemistry, photochemistry

Cite this article

Feng JunShao, Jiangyang, Gong Zhongliang, Zhong Yuwu. Amine-Amine Electronic Coupling through an Anthracene Bridge[J]. Chin. J. Org. Chem., 2016, 36(10): 2407-2412.

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蒽桥联的胺-胺电子耦合研究

Amine-Amine Electronic Coupling through an Anthracene Bridge

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