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
1. [1]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
2. [2]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
3. [3]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
4. [4]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
5. [5]
  Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
6. [6]
  Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
7. [7]
  Jingwen Wang , Minghao Wu , Xing Zuo , Yaofeng Yuan , Yahao Wang , Xiaoshun Zhou , Jianfeng Yan . Advances in the Application of Electrochemical Regulation in Investigating the Electron Transport Properties of Single-Molecule Junctions. University Chemistry, 2025, 40(3): 291-301. doi: 10.12461/PKU.DXHX202406023
8. [8]
  Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO₄:Yb³⁺,Er³⁺ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
9. [9]
  Jiaxuan Zuo , Kun Zhang , Jing Wang , Xifei Li . 锂离子电池Ni-Co-Mn基正极材料前驱体的形核调控及机制. Acta Physico-Chimica Sinica, 2025, 41(1): 2404042-. doi: 10.3866/PKU.WHXB202404042
10. [10]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
11. [11]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
12. [12]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
13. [13]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
14. [14]
  Yanan Jiang , Yuchen Ma . Brief Discussion on the Electronic Exchange Interaction in Quantum Chemistry Computations. University Chemistry, 2025, 40(3): 10-15. doi: 10.12461/PKU.DXHX202402058
15. [15]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
16. [16]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
17. [17]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
18. [18]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
19. [19]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
20. [20]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(391)
HTML views(28)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142