Chinese Journal of Organic Chemistry >
Amine-Amine Electronic Coupling through an Anthracene Bridge
Received date: 2016-06-13
Revised date: 2016-07-17
Online 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).
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 Vab was calculated to be 600 cm-1. In contrast, compound 3·+ displays an intense IVCT band in the NIR region with a Vab 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
Feng JunShao , Jiangyang , Gong Zhongliang , Zhong Yuwu . Amine-Amine Electronic Coupling through an Anthracene Bridge[J]. Chinese Journal of Organic Chemistry, 2016 , 36(10) : 2407 -2412 . DOI: 10.6023/cjoc201606020
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