Fullerene–Pyrrolidine Biferrocene Donor–Acceptor Triads: Synthesis and Effects of Fullerene[60] on the Electronic Communication of the Two Ferrocene Units in Biferrocene

Zhenyi Wu; Mian Jiang

doi:10.1071/CH15377

RESEARCH ARTICLE

Previous Next Contents Vol 69(4)

Fullerene–Pyrrolidine Biferrocene Donor–Acceptor Triads: Synthesis and Effects of Fullerene[60] on the Electronic Communication of the Two Ferrocene Units in Biferrocene

Zhenyi Wu ^A ^C and Mian Jiang ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

^B Department of Natural Sciences, University of Houston-Downtown, 1 Main Street, Houston, TX 77002, USA.

^C Corresponding author. Email: zywu@xmu.edu.cn

Australian Journal of Chemistry 69(4) 440-445 https://doi.org/10.1071/CH15377
Submitted: 25 June 2015 Accepted: 27 August 2015 Published: 29 September 2015

Abstract

A novel nanoscale molecule, fullerene[60]-based biferrocene (C₆₀-ph-Fc-Fc), was prepared via covalent grafting of biferrocene onto C₆₀ using 1,3-dipolar cycloaddition and was fully characterized by mass spectrometry, nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet-visible spectroscopy, and fluorescence spectroscopy. Cyclic voltammetry studies showed that C₆₀-ph-Fc-Fc undergoes four successive quasi-reversible processes in the potential window of –2.0~0.40 V (versus Fc⁺/Fc). The biferrocene (moiety) exhibited significant electronic communication between the two ferrocenyl groups both before and after grafting onto C₆₀. Grafting of fullerene led to weakening in the electronic interaction, and the comproportionation constant decreased by nearly five orders of magnitude from 1.56 × 10⁶ for Fc-Fc to 88 for C₆₀-ph-Fc-Fc, indicating that the electronic communication between halves of the biferrocene could be effectively modified by grafting of C₆₀. The temperature-dependent magnetic susceptibility (2–300 K) study showed that there was a strong antiferromagnetic interaction between the ferrocene Fe^II centres.

References

[1] (a) A. Donoli, A. Bisello, R. Cardena, C. Prinzivalli, M. Crisma, S. Santi, Organometallics 2014, 33, 1135.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXjt1Siurc%3D&md5=0c0966027730d860738dcb13c29065ecCAS |
      (b) W. R. Goetsch, P. V. Solntsev, C. Van Stappen, A. A. Purchel, S. V. Dudkin, V. N. Nemykin, Organometallics 2014, 33, 145.
         | Crossref | GoogleScholarGoogle Scholar |

[2] G. Bottari, O. Trukhina, M. Ince, T. Torres, Coord. Chem. Rev. 2012, 256, 2453.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XltVyiurw%3D&md5=2feaf6fd2d4753f7de1c416666caff8fCAS |

[3] M. Morana, H. Azimi, G. Dennler, H.-J. Egelhaaf, M. Scharber, K. Forberich, J. Hauch, R. Gaudiana, D. Waller, Z. Zhu, K. Hingerl, S. S. van Bavel, J. Loos, C. J. Brabec, Adv. Funct. Mater. 2010, 20, 1180.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXkt1ChsLY%3D&md5=f05ac90f6291aa76f1abca0e26565488CAS |

[4] (a) L. G. C. Rego, B. C. Hames, K. T. Mazon, J.-O. Joswig, J. Phys. Chem. C 2014, 118, 126.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvFSqu73F&md5=aa9c16a84a67234dea0c5cc04dabddaeCAS |
      (b) C. J. Ziegler, K. Chanawanno, A. Hasheminsasab, Y. V. Zatsikha, E. Maligaspe, V. N. Nemykin, Inorg. Chem. 2014, 53, 4751.
         | Crossref | GoogleScholarGoogle Scholar |

[5] J. Otsuki, T. Akasaka, K. Araki, Coord. Chem. Rev. 2008, 252, 32.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVaqtLbJ&md5=d54c65fadf6772c815116b35513d1129CAS |

[6] A. Monti, H. J. M. de Groot, F. Buda, J. Phys. Chem. C 2014, 118, 15600.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVOjtrnM&md5=b9c745a714f0c01938518c9079f5f47cCAS |

[7] (a) S. J. Dammer, P. V. Solntsev, J. R. Sabin, V. N. Nemykin, Inorg. Chem. 2013, 52, 9496.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1arsrzE&md5=dcc2855cc20e2157216de1251f7c268cCAS | 23919915PubMed |
      (b) E. Maligaspe, M. R. Hauwiller, Y. V. Zatsikha, J. A. Hinke, P. V. Solntsev, D. A. Blank, V. N. Nemykin, Inorg. Chem. 2014, 53, 9336.
         | Crossref | GoogleScholarGoogle Scholar |

[8] (a) V. Bandi, F. P. D’Souza, H. B. Gobeze, F. D’Souza, Chem. – Eur. J. 2015, 21, 2669.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitFaiurzE&md5=f53a8c8d68d38e75d1746b8747e4bdeeCAS | 25522294PubMed |
      (b) P. Cavigli, T. Da Ros, A. Kahnt, M. Gamberoni, M. T. Indelli, E. Iengo, Inorg. Chem. 2015, 54, 280.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) K. Barthelmes, J. Kuebel, A. Winter, M. Waechtler, C. Friebe, B. Dietzek, U. S. Schubert, Inorg. Chem. 2015, 54, 3159.
         | Crossref | GoogleScholarGoogle Scholar |

[9] T. Mochida, K. Takazawa, H. Matsui, M. Takahashi, M. Takeda, M. Sato, Y. Nishio, K. Kajita, H. Mori, Inorg. Chem. 2005, 44, 8628.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVOis73I&md5=467b47cc7d0abca58776a801170119ecCAS | 16271005PubMed |

[10] T. Y. Dong, T. Kambara, D. N. Hendrickson, J. Am. Chem. Soc. 1986, 108, 5857.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XltlCjtL8%3D&md5=c579e29f7d69df8a33f6e6c583121a37CAS | 22175341PubMed |

[11] (a) W. H. Morrison, S. Krogsrud, D. N. Hendrickson, Inorg. Chem. 1973, 12, 1998.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXkvVKku7Y%3D&md5=7560a77d18007fe86e453defffab8014CAS |
      (b) C. Levanda, K. Bechgaard, D. O. Cowan, J. Org. Chem. 1976, 41, 2700.
         | Crossref | GoogleScholarGoogle Scholar |

[12] (a) D. Wrobel, A. Graja, Coord. Chem. Rev. 2011, 255, 2555.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtF2rsLbE&md5=45fcf97db0663c3fd42df404b54e624dCAS |
      (b) W. J. Wang, Y. L. Lay, C. S. Chang, H. S. Chiu, K. S. Chuang, B. C. Wang, Synth. Met. 1997, 86, 2293.
         | Crossref | GoogleScholarGoogle Scholar |

[13] (a) D. M. Wood, W. J. Meng, T. K. Ronson, A. R. Stefankiewicz, J. K. M. Sanders, J. R. Nitschke, Angew. Chem., Int. Ed. 2015, 54, 3988.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXksVCru7k%3D&md5=a181d21bd63a9f1b8014f18e1d0dee90CAS |
      (b) L. Moreira, J. Calbo, B. M. Illescas, J. Arago, I. Nierengarten, B. Delavaux-Nicot, E. Ortí, N. Martín, J.-F. Nierengarten, Angew. Chem., Int. Ed. 2015, 54, 1255.
         | Crossref | GoogleScholarGoogle Scholar |

[14] (a) Z. Y. Wu, R. B. Huang, S. Y. Xie, L. S. Zheng, Dalton Trans. 2011, 40, 8353.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXpvFGgtrs%3D&md5=c7f683ead86e04855fe6d96a1fb546d0CAS | 21769337PubMed |
      (b) Z. Y. Wu, W. Wang, Fullerenes, Nanotubes, Carbon Nanostruct. 2015, 23, 131.
         | Crossref | GoogleScholarGoogle Scholar |

[15] R. J. Xie, L. M. Han, Q. L. Suo, H. L. Hong, M. H. Luo, J. Coord. Chem. 2010, 63, 1700.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntlanurY%3D&md5=94ad5520b73c4553574330f25ea24fdeCAS |

[16] S. Campidelli, P. Bourgun, B. Guintchin, J. Furrer, H. Stoeckli-Evans, I. M. Saez, J. W. Goodby, R. Deschenaux, J. Am. Chem. Soc. 2010, 132, 3574.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXitV2hsrY%3D&md5=9bc096988d937b358679e50efb86f530CAS | 20163119PubMed |

[17] A. N. Amin, M. E. El-Khouly, N. K. Subbaiyan, M. E. Zandler, S. Fukuzumi, F. D’Souza, Chem. Commun. 2012, 48, 206.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFGqu77O&md5=fac1b70ff1f1613cf0c30c6bd2322dc1CAS |

[19] J. L. Delgado, M. E. El-Khouly, Y. Araki, M. J. Gomez-Escalonilla, P. de la Cruz, F. Oswald, O. Ito, F. Langa, Phys. Chem. Chem. Phys. 2006, 8, 4104.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XovVWjsrs%3D&md5=31a0a0f7c61daf3ffcf2181fc59d71bcCAS | 17028699PubMed |

[21] Y. L. Wang, A. Rapakousiou, G. Chastanet, L. Salmon, J. Ruiz, D. Astruc, Organometallics 2013, 32, 6136.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFertbrI&md5=8592ce5f7a5eed561b4aeb91845f7bbeCAS |

[22] I. Shimizu, H. Umezawa, T. Kanno, T. Izumi, A. Kasahara, Bull. Chem. Soc. Jpn. 1983, 56, 2023.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXlvFGiurw%3D&md5=f7f0e0b483b31dae90d931769264611dCAS |

Fullerene–Pyrrolidine Biferrocene Donor–Acceptor Triads: Synthesis and Effects of Fullerene[60] on the Electronic Communication of the Two Ferrocene Units in Biferrocene

Abstract

References

Subscriber Login