Citation: Feng JunShao, Shao 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 shu

Amine-Amine Electronic Coupling through an Anthracene Bridge

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

Corresponding author: Zhong Yuwu, zhongyuwu@iccas.ac.cn
Received Date: 13 June 2016
Revised Date: 17 July 2016

Fund Project: National Natural Science Foundation of China 21271176Strategic Priority Research Program of the Chinese Academy of Sciences XDB12010400National Natural Science Foundation of China 21521062National Natural Science Foundation of China 21472196National Natural Science Foundation of China 21501183

Figures(6)

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.
- amines,
- charge transfer,
- electrochemistry,
- photochemistry
1. [1]
2. [2]
  Kong, D.-D.; Xue, L.-S.; Jang, R.; Liu, B.; Meng, X.-G.; Jin, S.; Ou, Y.-P.; Hao, X.; Liu, S.-H. Chem. Eur. J. 2015, 21, 9895. (b) Zhang, J.; Sun, C.-F.; Zhang, M.-X.; Hartl, F.; Yin, J.; Yu, G.-A.; Rao, L.; Liu, S. H. Dalton Trans. 2016, 45, 768.
3. [3]
  Zhang, D.-B.; Wang, J.-Y.; Wen, H.-M.; Chen, Z.-N. Organometallics 2014, 33, 4738.
4. [4]
  Tang, J.-H.; Shao, J.-Y.; He, Y.-Q.; Wu, S.-H.; Yao, J.; Zhong, Y.-W. Chem. Eur. J. 2016, 22, 10341.
5. [5]
  Zhong, Y.-W.; Gong, Z.-L.; Shao, J.-Y.; Yao, J. Coord. Chem. Rev. 2016, 312, 22.
6. [6]
  Hildebrandt, A.; Lang, H. Organometallics 2013, 32, 5640.
7. [7]
  Gong, Z.-L.; Zhong, Y.-W. Sci. China Chem. 2015, 58, 1444.
8. [8]
  Chen, T.; Tan, Y. N.; Zhang, Y.; Zhang, Y. Y.; Meng, M.; Lei, H.; Chen, L.; Liu, C. Y. Chem. Eur. J. 2015, 21, 2353.
9. [9]
  Tang, J.-H.; Yao, C.-J.; Cui, B.-B.; Zhong, Y.-W. Chem. Rec. 2016, 16, 754. (b) Shao, J.-Y.; Yao, C.-J.; Cui, B.-B.; Gong, Z.-L.; Zhong, Y.-W. Chin. Chem. Lett. 2016, 27, 1105.
10. [10]
  Wu, X.; Wu, Y.; Zhang, C.; Nie, H.; Lei, L.; Qin, C.; Wang, C.; Bai, X.; Wang, W. RSC Adv. 2015, 5, 58843. (b) Ma, X.; Wu, Y.; Wen, H.; Niu, H.; Wang, C.; Qin, C.; Bai, X.; Lei, L.; Wang, W. RSC Adv. 2016, 6, 4564.
11. [11]
  Fan, H.; Zhu, X. Sci. China Chem. 2015, 58, 922.
12. [12]
  Xiao, J.; Shi, J.; Li, D.; Meng, Q. Sci. China Chem. 2015, 58, 221.
13. [13]
  Tao, Y.; Yang, C.; Qin, J. Chem. Soc. Rev. 2011, 40, 2943.
14. [14]
  Yao, L.; Yang, B.; Ma, Y.-G. Sci. China Chem. 2014, 57, 335.
15. [15]
  Hankache, J.; Wenger, O. S. Chem. Rev. 2011, 111, 5138. (b) Heckmann, S.; Lambert, C. Angew. Chem., Int. Ed. 2012, 51, 326.
16. [16]
  Shen, J.-J.; Shao, J.-Y.; Zhu, X.; Zhong, Y.-W. Org. Lett. 2016, 18, 256.
17. [17]
  Yoshizawa, M.; Klosterman, J. K. Chem. Soc. Rev. 2014, 43, 1885.
18. [18]
  Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208.
19. [19]
20. [20]
21. [21]
  Lambert, C.; Risko, C.; Coropceanu, V.; Schelter, J.; Amthor, S.; Gruhn, N. E.; Durivage, J. C.; Bredas, J.-L. J. Am. Chem. Soc. 2005, 127, 8508.
22. [22]
  Su, Y.; Wang, X.; Li, Y.; Song, Y.; Sui, Y.; Wang, X. Angew. Chem., Int. Ed. 2015, 54, 1634. (b) Wang, X.; Zhang, Z.; Song, Y.; Su, Y.; Wang, X. Chem. Commun. 2015, 51, 11822.
23. [23]
  Vila, N.; Zhong, Y.-W.; Henderson, J. C.; Abruna, H. D. Inorg. Chem. 2010, 49, 796.
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