双二茂铁基吡咯衍生物电荷交互通道

doi:10.3866/PKU.WHXB201411061

Abstract

Abstract:

2,5-Diferrocenyl-1-(3-trifluorom-ethylphenyl)-pyrrole (1), 2,5-diferrocenyl-1-(4-fluorophenyl)-pyrrole (2), 2,5-diferrocenyl-1-phenyl pyrrole (3), 2,5-diferro-cenyl-1-(4-ethylphenyl)-pyrrole (4), and 2,5-diferrocenyl- 1-(4-ethoxyphenyl)-pyrrole (5) were prepared by the one-pot cycloaddition reaction of ferrocenyl alkyne. The 2,5-diferrocenyl-1-phenyl-1-pyrrole derivatives were characterized by elemental analysis, Fourier-transform infrared (FTIR) spectroscopy, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy. The influence of substituents at the phenyl moiety on the electronic interaction was studied using cyclic voltammetry (CV) and density functional theory (DFT) calculations. A linear relationship was observed between the first oxidation potential (E_a1), oxidation potential difference (ΔE) with Hammett constant (Hammett σ) of the substituent, pyrrole ¹H NMR chemical shift (δ), and pyrrole N natural bond orbital (NBO) charge. A high N charge density weakened the electronic interaction, and vice versa. Electron transfer between the two ferrocenyl units of these diferrocenyl pyrrole derivatives was influenced by the N charge density.

Key words: Diferrocenyl, Pyrrole derivative, Channel of electronic interaction

Click here to download Supporting Info material in PDF type

HU Yu-Qiang, ZHU Ning, HAN Li-Min. Channel of Electronic Interactions in Diferrocenyl Pyrrole Derivatives[J]. Acta Phys. -Chim. Sin. 2015, 31(2), 227-236. doi: 10.3866/PKU.WHXB201411061

References

(1) Dunitz, J. D.; Orgel, L. E.; Rich, A. Acta Cryst. 1956, 9, 373. doi: 10.1107/S0365110X56001091
(2) Seiler, P.; Dunitz, J. D. Acta Cryst. 1979, B35, 1068.
(3) Stephen, B.; Dermot, O. H. Chem. Rev. 1997, 97, 637. doi: 10.1021/cr960083v
(4) Gilbert, M. B.; Thomas, J. M.; Cowan, D. O.; Vanda, C. L.; Kaufman, F.; Roling, P. V.; Rausch, M. D. Inorg. Chem. 1975, 14, 506. doi: 10.1021/ic50145a011
(5) Pfaff, U.; Hildebrandt, A.; Schaarschmidt, D.; Ruffer, T.; Low, P. J.; Lang, H. Organometallics 2013, 32, 6106. doi: 10.1021/om4007533
(6) Dammer, S. J.; Solntsev, P. V.; Sabin, J. R.; Nemykin, V. N. Inorg. Chem. 2013, 52, 9496. doi: 10.1021/ic401163y
(7) Wang, J.; Feng, L. M.; Ma, F. J.; Lin, F.; Xie, L. L.; Yuan, Y. F. Chin. J. Org. Chem. 2012, 32, 1479. [王静, 冯丽敏, 马飞娟, 林芬, 谢莉莉, 袁耀锋. 有机化学学报, 2012, 32, 1479.] doi: 10.6023/cjoc1112291
(8) Klimova, E. I.; Garcia, M. M.; Alamo, M. F.; Churakov, A. V.; Maya, S. C.; Beletskaya, I. P. Polyhedron 2014, 68, 272. doi: 10.1016/j.poly.2013.11.003
(9) Morrison, J.W. H.; Krogsrud, S.; Hendrickson, D. N. Inorg. Chem. 1973, 12, 1998. doi: 10.1021/ic50127a009
(10) Richardson, D. E.; Taube, H. Coord. Chem. Rev. 1984, 60, 107. doi: 10.1016/0010-8545(84)85063-8
(11) Astruc, D. Accounts Chem. Res. 1997, 30, 383. doi: 10.1021/ar970007u
(12) Cowan, D. O.; Park, J.; Pittman, C. U.; Sasaki, Y.; Mukherjee, T. K.; Diamond, N. A. J. Am. Chem. Soc. 1972, 94, 5110. doi: 10.1021/ja00769a069
(13) Yamamoto, T.; Seki, K.; Yamamoto, A.; Motoyama, I.; Sano, H. Inorg. Chim. Acta 1983, 73, 75. doi: 10.1016/S0020-1693(00)90829-6
(14) Dong, T. Y.; Ke, T. J.; Peng, S. M.; Yeh, S. K. Inorg. Chem. 1989, 28, 2103. doi: 10.1021/ic00310a018
(15) Ribou, A. C.; Launay, J. P.; Sachtleben, M. L.; Li, H.; Spangler, C.W. Inorg. Chem. 1996, 35, 3735. doi: 10.1021/ic951376u
(16) Aguado, J. E.; Crespo, O.; Gimeno, M. C.; Jones, P. G.; Laguna, A.; Nieto, Y. Eur. J. Inorg. Chem. 2008, 3031.
(17) Carugo, O.; Santis, G. D.; Fabbrizzi, L.; Licchelli, M.; Monichino, A.; Pallavicini, P. Inorg. Chem. 1992, 31, 765. doi: 10.1021/ic00031a014
(18) Hollandsworth, C. B.; Hollis, J.W. G.; Slebodnick, C.; Deck, P. A. Organometallics 1999, 18, 3610. doi: 10.1021/om990321n
(19) Camire, N.;Westerhoff, U. T. M.; Geiger,W. E. J. Organomet. Chem. 2001, 637, 823.
(20) Tahara, K.; Akita, T.; Katao, S.; Kikuchi, J. I. Dalton Trans. 2014, 43, 1368. doi: 10.1039/c3dt52503a
(21) Bruna, S.; Perles, J.; Nieto, D.; Ana, M.; Vadillo, G.; Cuadrado, I. J. Organomet. Chem. 2014, 751, 769. doi: 10.1016/j.jorganchem.2013.07.052
(22) Alvarez, J.; Kaifer, A. E. Organometallics 1999, 18, 5733. doi: 10.1021/om990678r
(23) Qin, S. N.; Hu, J. R.; Chen, Z. L.; Liang, F. P. J. Coord. Chem. 2011, 64, 3718. doi: 10.1080/00958972.2011.630072
(24) Javed, F.; Altaf, A. A.; Badshah, A.; Tahir, M. N.; Siddiq, M.; Rehman, Z. U.; Shah, A.; Ullah, S.; Lal, B. J. Coord. Chem. 2012, 65, 969. doi: 10.1080/00958972.2012.664769
(25) Liu, Z. S.; Zhu, N.; Han, L. M.; Xie, R. J.; Hong, H. L.; Suo, Q. L. J. Coord. Chem. 2012, 65, 2804. doi: 10.1080/00958972.2012.704024
(26) Han, L. M.; Hu, Y. Q.; Suo, Q. L.; Luo, M. H.;Weng, L. H. J. Coord. Chem. 2010, 63, 600. doi: 10.1080/00958970903582688
(27) Xie, R. J.; Han, L. M.; Gao, Y. Y.; Zhu, N.; Hong, H. L.; Suo, Q. L. J. Coord. Chem. 2012, 65, 4086. doi: 10.1080/00958972.2012.732696
(28) Xie, R. J.; Han, L. M.; Suo, Q. L.; Hong, H. L.; Luo, M. H. J. Coord. Chem. 2010, 63, 1700. doi: 10.1080/00958972.2010.487102
(29) Xie, R. J.; Han, L. M.; Zhu, N.; Hong, H. L.; Suo, Q. L. J. Coord. Chem. 2011, 64, 3180. doi: 10.1080/00958972.2011.616198
(30) Xie, R. J.; Han, L. M.; Zhu, N.; Hong, H. L.; Suo, Q. L.; Fu, P. Polyhedron 2012, 38, 7.
(31) Hu, Y. Q.; Han, L. M.; Zhu, N.; Hong, H. L.; Xie, R. J. J. Coord. Chem. 2013, 66, 3481. doi: 10.1080/00958972.2013.841902
(32) Wang,Y. Q.; Han, L. M.; Suo, Q. L.; Zhu, N.; Hao, J. M.; Xie, R. J. Polyhedron 2013, 54, 221. doi: 10.1016/j.poly.2013.02.043
(33) Tarraga, A.; Molina, P.; Curiel, D.; Velasco, M. D. Tetrahedron Letters 2002, 43, 8453. doi: 10.1016/S0040-4039(02)02097-X
(34) Hildebrandt, A.; Schaarschmidt, D.; As, L. V.; Swarts, J. C.; Lang, H. Inorg. Chim. Acta 2011, 374, 112. doi: 10.1016/j.ica.2011.02.058
(35) Hildebrandt, A.; Lang, H. Dalton Trans. 2011, 40, 11831. doi: 10.1039/c1dt10997a
(36) Hildebrandt, A.; Schaarschmidt, D.; Lang, H. Organometallics 2011, 30, 556. doi: 10.1021/om100914m
(37) Hansch, C.; Leo, A.; Taft, R.W. Chem. Rev. 199l, 97, 165.
(38) Nemukhina, A. V.;Weinhold, F. J. Chem. Phys. 1993, 98, 1329. doi: 10.1063/1.464299
(39) Badenhoopa, J. K.;Weinhold, F. J. Chem. Phys. 1997, 107, 5406. doi: 10.1063/1.474248
(40) Carpenter, J. E.;Weinhold, F. J. Chem. Phys. 1988, 92, 4306. doi: 10.1021/j100326a013
(41) Zimmerman, H. E.;Weinhold, F. J. Org. Chem. 2013, 78, 1844. doi: 10.1021/jo301620k
(42) Drake, S. R.; Khattar, R. Organomet. Synth. 1988, 4, 234.
(43) Han, L. M.; Zhang, L. F.; Zhang, G. B.; Yin, Z. G. Chin. J. Inorg. Chem. 2008, 24, 1807. [韩利民, 张利峰, 张广斌, 尹志国. 无机化学学报, 2008, 24, 1807.]
(44) Sorensen, A. R.; Overgaard, L.; Johannsen, I. Synthetic Metals. 1993, 55, 1626. doi: 10.1016/0379-6779(93)90296-9
(45) Imler, G. H.; Lu, Z.; Kistler, K. A.; Carroll, P. J.;Wayland, B. B.; Zdilla, M. J. Inorg. Chem. 2012, 51, 10122. doi: 10.1021/ic300435t
(46) Feng, X.; Tong, B.; Shen, J. B.; Shi, J. B.; Han, T. Y.; Chen, L.; Zhi, J. G.; Lu, P.; Ma, Y. G.; Dong, Y. P. J. Phys. Chem. B 2010, 114, 16731. doi: 10.1021/jp108254g
(47) Zheng, Q.W.; Hua, R. M. Tetrahedron Letters 2010, 51, 4512. doi: 10.1016/j.tetlet.2010.06.092
(48) Smith, M. B.; March, J. March ′s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed.;Wiley: New Jersey, 2007; pp 54-55.
(49) Corry, A. J.; Goel, A.; Kenny, P. T. M. Inorg. Chim. Acta 2012, 384, 293. doi: 10.1016/j.ica.2011.12.021
(50) Schaarschmidt, D.; Hildebrandt, A.; Bock, S.; Lang, H. Journal of Organometallic Chemistry 2014, 751, 742. doi: 10.1016/j.jorganchem.2013.07.080
(51) Liu, S. G.; Perez, I.; Martin, N.; Echegoyen, L. J. Org. Chem. 2000, 65, 9092. doi: 10.1021/jo001149w
(52) Schubert, C.;Wielopolski, M.; Mewes, L. H.; Rojas, G. D. M.; Pol, C. V. D.; Moss, K. C.; Bryce, M. R.; Moser, J. E.; Clark, T.; Guldi, D. M. Chem. Eur. J. 2013, 19, 7575. doi: 10.1002/chem.201204055
(53) Justin, T. K. R.; Lin, J. T.;Wen, Y. S. Organometallics 2000, 19, 1008. doi: 10.1021/om9908635
(54) Levanda, C.; Bechgaard, K.; Cowan, D. O. J. Org. Chem. 1976, 41, 2700. doi: 10.1021/jo00878a008
(55) Ribou, A. C.; Launay, J. P.; Sachtleben, M. L.; Li, H.; Spangler, C.W. Inorg. Chem. 1996, 35, 3735. doi: 10.1021/ic951376u
(56) Glendening, E. D.; Landis, C. R.;Weinhold, F. Journal of Computational Chemistry 2013, 34, 1429. doi: 10.1002/jcc.23266
(57) Weinhold, F. Journal of Computational Chemistry 2012, 33, 2363. doi: 10.1002/jcc.v33.30
(58) Reed, A. E.;Weinhold, F. J. Chem. Phys. 1985, 84, 1736.
(59) Reed, A. E.;Weinhold, F. J. Chem. Phys. 1986, 84, 5687. doi: 10.1063/1.449928
(60) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision A.01; Gaussian Inc.: Pittsburgh, PA, 2003.
(61) Smith, M. B.; March, J. March ′s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed.;Wiley: New Jersey, 2007; pp 19-20.
(62) Goetsch,W. R.; Solntsev, P. V.; Stappen, C. V.; Purchel, A. A.; Dudkin, S. V.; Nemykin, V. N. Organometallics 2014, 33, 145. doi: 10.1021/om400901w
(63) Fink, H.; Long, N. J.; Martin, A. J.; Opromolla, G.; White, A. J. P.;Williams, D. J.; Zanello, P. Organometallics 1997, 16, 2646. doi: 10.1021/om9701027
(64) Patoux, C.; Coudret, C.; Launay, J. P.; Joachim, C.; Gourdon, A. Inorg. Chem. 1997, 36, 5037. doi: 10.1021/ic970013m
(65) Chen, Y. J.; Pan, D. S.; Chiu, C. F.; Su, J. X.; Lin, S. J.; Kwan, K. S. Inorg. Chem. 2000, 39, 953. doi: 10.1021/ic991084j

[1]	Liangliang Song, Haoyan Liang, Shunqing Li, Bao Qiu, Zhaoping Liu. Challenges and strategies on high-manganese Li-rich layered oxide cathodes for ultrahigh-energy-density batteries [J]. Acta Phys. -Chim. Sin., 2025, 41(8): 100085-.
[2]	Caiyun Jin, Zexuan Wu, Guopeng Li, Zhan Luo, Nian-Wu Li. Phosphazene-based flame-retardant artificial interphase layer for lithium metal batteries [J]. Acta Phys. -Chim. Sin., 2025, 41(8): 100094-.
[3]	Yu Peng, Jiawei Chen, Yue Yin, Yongjie Cao, Mochou Liao, Congxiao Wang, Xiaoli Dong, Yongyao Xia. Tailored cathode electrolyte interphase via ethylene carbonate-free electrolytes enabling stable and wide-temperature operation of high-voltage LiCoO₂ [J]. Acta Phys. -Chim. Sin., 2025, 41(8): 100087-.
[4]	Mingjie Lei, Wenting Hu, Kexin Lin, Xiujuan Sun, Haoshen Zhang, Ye Qian, Tongyue Kang, Xiulin Wu, Hailong Liao, Yuan Pan, Yuwei Zhang, Diye Wei, Ping Gao. Accelerating the reconstruction of NiSe₂ by Co/Mn/Mo doping for enhanced urea electrolysis [J]. Acta Phys. -Chim. Sin., 2025, 41(8): 100083-.
[5]	Zeqiu Chen, Limiao Cai, Jie Guan, Zhanyang Li, Hao Wang, Yaoguang Guo, Xingtao Xu, Likun Pan. Advanced electrode materials in capacitive deionization for efficient lithium extraction [J]. Acta Phys. -Chim. Sin., 2025, 41(8): 100089-.
[6]	Mingxuan Qi, Lanyu Jin, Honghe Yao, Zipeng Xu, Teng Cheng, Qi Chen, Cheng Zhu, Yang Bai. Recent progress on electrical failure and stability of perovskite solar cells under reverse bias [J]. Acta Phys. -Chim. Sin., 2025, 41(8): 100088-.
[7]	Chaoqiong Zhu, Ziming Cai, Peizhong Feng, Weichen Zhang, Kezhen Hui, Xiuhua Cao, Zhenxiao Fu, Xiaohui Wang. Reliability Mechanisms of the Ultrathin-Layered BaTiO₃-Based BME MLCC [J]. Acta Phys. -Chim. Sin., 2024, 40(1): 2304015-.
[8]	Xinxuan Duan, Marshet Getaye Sendeku, Daoming Zhang, Daojin Zhou, Lijun Xu, Xueqing Gao, Aibing Chen, Yun Kuang, Xiaoming Sun. Tungsten-Doped NiFe-Layered Double Hydroxides as Efficient Oxygen Evolution Catalysts [J]. Acta Phys. -Chim. Sin., 2024, 40(1): 2303055-.
[9]	Qian Wu, Qingping Gao, Bin Shan, Wenzheng Wang, Yuping Qi, Xishi Tai, Xia Wang, Dongdong Zheng, Hong Yan, Binwu Ying, Yongsong Luo, Shengjun Sun, Qian Liu, Mohamed S. Hamdy, Xuping Sun. Recent Advances in Self-Supported Transition-Metal-Based Electrocatalysts for Seawater Oxidation [J]. Acta Phys. -Chim. Sin., 2023, 39(12): 2303012-.
[10]	Luwei Peng, Yang Zhang, Ruinan He, Nengneng Xu, Jinli Qiao. Research Advances in Electrocatalysts, Electrolytes, Reactors and Membranes for the Electrocatalytic Carbon Dioxide Reduction Reaction [J]. Acta Phys. -Chim. Sin., 2023, 39(12): 2302037-.
[11]	Kuangyu Wang, Kai Liu, Hui Wu. Molten Alkali Metal Batteries Based on Solid Electrolytes [J]. Acta Phys. -Chim. Sin., 2023, 39(12): 2301009-.
[12]	Shuyi Zheng, Jia Wu, Ke Wang, Mengchen Hu, Huan Wen, Shibin Yin. Electronic Modulation of Ni-Mo-O Porous Nanorods by Co Doping for Selective Oxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Evolution [J]. Acta Phys. -Chim. Sin., 2023, 39(12): 2301032-.
[13]	Zheng-Min Wang, Qing-Ling Hong, Xiao-Hui Wang, Hao Huang, Yu Chen, Shu-Ni Li. RuP Nanoparticles Anchored on N-doped Graphene Aerogels for Hydrazine Oxidation-Boosted Hydrogen Production [J]. Acta Phys. -Chim. Sin., 2023, 39(12): 2303028-.
[14]	Jie Wang, Guigao Liu, Qinbai Yun, Xichen Zhou, Xiaozhi Liu, Ye Chen, Hongfei Cheng, Yiyao Ge, Jingtao Huang, Zhaoning Hu, Bo Chen, Zhanxi Fan, Lin Gu, Hua Zhang. Epitaxial Growth of Unconventional 4H-Pd Based Alloy Nanostructures on 4H-Au Nanoribbons towards Highly Efficient Electrocatalytic Methanol Oxidation [J]. Acta Phys. -Chim. Sin., 2023, 39(10): 2305034-.
[15]	Weifeng Xia, Chengyu Ji, Rui Wang, Shilun Qiu, Qianrong Fang. Metal-Free Tetrathiafulvalene Based Covalent Organic Framework for Efficient Oxygen Evolution Reaction [J]. Acta Phys. -Chim. Sin., 2023, 39(9): 2212057-0.

Channel of Electronic Interactions in Diferrocenyl Pyrrole Derivatives

PDF

Like

Knowledge

Abstract

Supporting Info

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0