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
-
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.
-
-
[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) Nishihara, H. Bull. Chem. Soc. Jpn. 2001, 74 (1), 19. doi: 10.1246/bcsj.74.19
-
[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) Muraoka, H.; Watanabe, Y.; Takahashi, A.; Kamoto, H.; Ogawa, S. Heteroatom Chem. 2014, 25, 473. doi: 10.1002/hc.21156
-
[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) Xu, G. L.; Xi, B.; Updegraff, J. B.; Protasiewicz, J. D.; Ren, T.Organometallics 2006, 25 (22), 5213. doi: 10.1021/om0607550
-
[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) Li, Y.; Josowicz, M.; Tolbert, L. M. J. Am. Chem. Soc. 2010, 132 (30), 10374. doi: 10.102/ja101585z
-
[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) 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) Yoshida, J.; Kuwahara, K.; Yuge, H. J. Organomet. Chem.2014, 756, 19. doi: 10.1016/j.jorganchem.2014.01.018
-
[12]
(12) Tanaka, Y.; Koike, T.; Akita, M. Eur. J. Inorg. Chem. 2010, 3571. doi: 10.1002/ejic.201000661
-
[13]
(13) Moriuchi, T.; Hirao, T. Tetrahedron Lett. 2007, 48 (29), 5099. doi: 10.1016/j.tetlet.2007.05.095
-
[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) Alvarez, J.; Kaifer, A. E. Organometallics 1999, 18 (26), 5733. doi: 10.1021/om990678r
-
[16]
(16) Tannai, H.; Tsuge, K.; Sasaki, Y. Inorg. Chem. 2005, 44 (15), 5206. doi: 10.1021/ic050672w
-
[17]
(17) de Rege, P. J.; Williams, S. A.; Therien, M. J. Science 1995, 269, 1409. doi: 10.1126/science.7660123
-
[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) 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) Goeltz, J. C.; Kubiak, C. P. J. Am. Chem. Soc. 2010, 132 (49), 17390. doi: 10.1021/ja108841k
-
[21]
(21) Sun, H.; Steeb, J.; Kaifer, A. E. J. Am. Chem. Soc. 2006, 128(9), 2820. doi: 10.1021/ja060386z
-
[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) Sijbesma, R. P.; Meijer, E.W. Chem. Commun. 2003, 5. doi: 10.1039/B205873C
-
[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) 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) Demadis, K. D.; Hartshorn, C. M.; Meyer, T. J. Chem. Rev.2001, 101 (9), 2655. doi: 10.1021/cr990413m
-
[1]
-
-
[1]
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
-
[2]
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
-
[3]
Haiyu Nie , Chenhui Zhang , Fengpei Du . Ideological and Political Design for the Preparation, Characterization and Particle Size Control Experiment of Nanoemulsion. University Chemistry, 2024, 39(2): 41-46. doi: 10.3866/PKU.DXHX202306055
-
[4]
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
-
[5]
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
-
[6]
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
-
[7]
Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
-
[8]
Yanhui XUE , Shaofei CHAO , Man XU , Qiong WU , Fufa WU , Sufyan Javed Muhammad . Construction of high energy density hexagonal hole MXene aqueous supercapacitor by vacancy defect control strategy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1640-1652. doi: 10.11862/CJIC.20240183
-
[9]
Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O2的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
-
[10]
Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
-
[11]
Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
-
[12]
Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO2 Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
-
[13]
Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
-
[14]
Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag3PO4/C3N5 Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
-
[15]
Qin Hu , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Ni掺杂构建电子桥及激活MoS2惰性基面增强光催化分解水产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2406024-. doi: 10.3866/PKU.WHXB202406024
-
[16]
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
-
[17]
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
-
[18]
Jinglun Wang , Hu Zhou , Baishu Zheng , Guobin Li , Ming Yue , Zhihua Zhou . Exploration and Practice of “Four Cooperations and Four Integrations” to Cultivate Innovative Talents in Chemical Materials in Local Colleges. University Chemistry, 2024, 39(7): 93-98. doi: 10.12461/PKU.DXHX202405013
-
[19]
Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO3 for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
-
[20]
Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(338)
- HTML views(28)