Acta Phys. -Chim. Sin. ›› 2016, Vol. 32 ›› Issue (3): 611-616.doi: 10.3866/PKU.WHXB201601044

• ARTICLE • Previous Articles     Next Articles

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

Su-Min WANG,Rong-Na ZHAO,Qi-Guan WANG*(),Hao GUO,Jin-Hua LI,Wen-Hui ZHANG   

  • Received:2015-11-09 Published:2016-03-04
  • Contact: Qi-Guan WANG
  • Supported by:
    the National Natural Science Foundation of China(21103133);Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education, Natural Science Foundation of Shaanxi Province, China(2015JM5224);Shaanxi Provincial Education Department Program, China(2013JK0678);National Training Programs of Innovation and Entrepreneurship for Undergraduates, China(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.

Key words: Ureidopyrimidinone, Quadruple hydrogen bonding, Electronic communication, Control, Ferrocene


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