Citation: WANG Su-Min, ZHAO Rong-Na, WANG Qi-Guan, GUO Hao, LI Jin-Hua, ZHANG Wen-Hui. Ureidopyrimidinone Quadruple Hydrogen-Bonded Ferrocene Dimer: Control of Electronic Communication[J]. Acta Physico-Chimica Sinica, ;2016, 32(3): 611-616. doi: 10.3866/PKU.WHXB201601044 shu

Ureidopyrimidinone Quadruple Hydrogen-Bonded Ferrocene Dimer: Control of Electronic Communication

1.
Shaanxi Key Laboratory of Photoelectric Functional Materials and Devices, School of Materials and Chemical Engineering, Xi'an Technological University, Xi'an 710032, P. R. China

Corresponding author: WANG Qi-Guan,
Received Date: 9 November 2015
Available Online: 24 December 2015
Fund Project: 国家自然科学基金(21103133) (21103133)教育部留学归国科研启动基金,陕西省自然科学基金(2015JM5224) (2015JM5224)陕西省教育厅科研计划项目(2013JK0678) (2013JK0678)大学生创新创业训练计划项目(201510702030)资助 (201510702030)

A ferrocene homodimer was assembled via the ureidopyrimidinone quadruple hydrogen-bonded module in this paper. Remarkable electronic communication was found between the two ferrocene centers across the ureidopyrimidinone bridge in chloroform. The separation between the two redox potentials (ΔE) of the ferrocenyl moieties was 260 mV. Upon protonation of the hydrogen-bonded bridge by successive addition of 0.5, 1, and 2 equivalents of trifluoroacetic acid, the extent of the electronic communication between the subunits gradually lowered, with ΔE decreasing to 150, 100, and 0 mV, respectively, because of the stepwise dissociation of the pyrimidinone hydrogen-bonded bridge. This phenomenon is reversible, and the initial voltammogram can be recovered stepwise by successive addition of triethylamine, demonstrating effective control of the electronic communication between two ferrocene centers.
- Ureidopyrimidinone,
- Quadruple hydrogen bonding,
- Electronic communication,
- Control,
- Ferrocene
1. [1]
  (1) Venkatasubbaiah, K.; Zakharov, L. N.; Kassel, W. S.; Rheingold, A. L.; Jäkle, F. Angew. Chem. 2005, 117 (34), 5564. doi: 10.1002/ange.200502148
2. [2]
  (2) Nishihara, H. Bull. Chem. Soc. Jpn. 2001, 74 (1), 19. doi: 10.1246/bcsj.74.19
3. [3]
  (3) Ceccon, A.; Santi, S.; Orian, L.; Bisello, A. Coordin. Chem. Rev. 2004, 248, 683. doi: 10.1016/j.ccr.2004.02.007
4. [4]
  (4) Muraoka, H.; Watanabe, Y.; Takahashi, A.; Kamoto, H.; Ogawa, S. Heteroatom Chem. 2014, 25, 473. doi: 10.1002/hc.21156
5. [5]
  (5) Xu, G. L.; Crutchley, R. J.; DeRosa, M. C.; Pan, Q. J.; Zhang, H. X.; Wang, X.; Ren, T. J. Am. Chem. Soc. 2005, 127 (38), 13354. doi: 10.1021/ja0534452
6. [6]
  (6) Xu, G. L.; Xi, B.; Updegraff, J. B.; Protasiewicz, J. D.; Ren, T.Organometallics 2006, 25 (22), 5213. doi: 10.1021/om0607550
7. [7]
  (7) Iyoda, M.; Kondo, T.; Okabe, T.; Matsuyama, H.; Sasaki, S.; Kuwatani, Y. Chem Lett. 1997, 26 (1), 35. doi: 10.1246/cl.1997.35
8. [8]
  (8) Li, Y.; Josowicz, M.; Tolbert, L. M. J. Am. Chem. Soc. 2010, 132 (30), 10374. doi: 10.102/ja101585z
9. [9]
  (9) Hu, Y. Q.; Zhu, N.; Han, L. M. Acta Phys. -Chim. Sin. 2015, 31(2), 227. [胡宇强, 竺宁, 韩利民. 物理化学学报, 2015, 31(2), 227.] doi: 10.3866/PKU.WHXB201411061
10. [10]
  (10) Mahmoud, K.; Long, Y. T.; Schatte, G.; Kraatz, H. B.J. Organomet. Chem. 2004, 689, 2250. doi: 10.1016/j.jorganchem.2004.04.016
11. [11]
  (11) Yoshida, J.; Kuwahara, K.; Yuge, H. J. Organomet. Chem.2014, 756, 19. doi: 10.1016/j.jorganchem.2014.01.018
12. [12]
  (12) Tanaka, Y.; Koike, T.; Akita, M. Eur. J. Inorg. Chem. 2010, 3571. doi: 10.1002/ejic.201000661
13. [13]
  (13) Moriuchi, T.; Hirao, T. Tetrahedron Lett. 2007, 48 (29), 5099. doi: 10.1016/j.tetlet.2007.05.095
14. [14]
  (14) Di Pietro, C. D.; Serroni, S.; Campagna, S.; Gandolfi, M. T.; Ballardini, R.; Fanni, S.; Browne, W. R.; Vos, J. G. Inorg. Chem. 2002, 41 (11), 2871. doi: 10.1021/ic0112894
15. [15]
  (15) Alvarez, J.; Kaifer, A. E. Organometallics 1999, 18 (26), 5733. doi: 10.1021/om990678r
16. [16]
  (16) Tannai, H.; Tsuge, K.; Sasaki, Y. Inorg. Chem. 2005, 44 (15), 5206. doi: 10.1021/ic050672w
17. [17]
  (17) de Rege, P. J.; Williams, S. A.; Therien, M. J. Science 1995, 269, 1409. doi: 10.1126/science.7660123
18. [18]
  (18) Sánchez, L.; Sierra, M.; Martín, N.; Myles, A. J.; Dale, T. J.; Rebek, J.; Seitz, W.; Guldi, D. M. Angew. Chem. Int. Edit.2006, 45 (28), 4637. doi: 10.1002/anie.200601264
19. [19]
  (19) Wilkinson, L. A.; McNeill, L.; Meijer, A. J. H. M.; Patmore, N.J. J. Am. Chem. Soc. 2013, 135 (5), 1723. doi: 10.1021/ja312176x
20. [20]
  (20) Goeltz, J. C.; Kubiak, C. P. J. Am. Chem. Soc. 2010, 132 (49), 17390. doi: 10.1021/ja108841k
21. [21]
  (21) Sun, H.; Steeb, J.; Kaifer, A. E. J. Am. Chem. Soc. 2006, 128(9), 2820. doi: 10.1021/ja060386z
22. [22]
  (22) Beijer, F. H.; Sijbesma, R. P.; Kooijman, H.; Spek, A. L.; Meijer, E.W. J. Am. Chem. Soc. 1998, 120 (27), 6761. doi: 10.1021/ja974112a
23. [23]
  (23) Sijbesma, R. P.; Meijer, E.W. Chem. Commun. 2003, 5. doi: 10.1039/B205873C
24. [24]
  (24) Alexander, A. M.; Bria, M.; Brunklaus, G.; Caldwell, S.; Cooke, G.; Garety, J. F.; Hewage, S. G.; Hocquel, Y.; McDonald, N.; Rabani, G.; Rosair, G.; Smith, B. O.; Spiess, H.W.; Rotello V. M.; Woisel, P. Chem. Commun. 2007, 2246. doi: 10.1039/B703070C
25. [25]
  (25) Zhao, Y. P.; Zhao, C. C.; Wu, L. Z.; Zhang, L. P.; Tung, C. H.; Pan, Y. J. J. Org. Chem. 2006, 71 (5), 2143. doi: 10.1021/jo051932u
26. [26]
  (26) Demadis, K. D.; Hartshorn, C. M.; Meyer, T. J. Chem. Rev.2001, 101 (9), 2655. doi: 10.1021/cr990413m
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沈阳化工大学材料科学与工程学院沈阳 110142