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



冯骏a,b, 邵将洋a, 龚忠亮a, 钟羽武a,b   

  1. 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,
  • 基金资助:


Amine-Amine Electronic Coupling through an Anthracene Bridge

Feng JunShaoa,b, Jiangyanga, Gong Zhonglianga, Zhong Yuwua,b   

  1. 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).

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