Study of the contact charge transfer behavior between cryptophanes (A and E) and fullerene by absorption, fluorescence and 1H NMR spectroscopy

Caihong Zhang; Weili Shen; Ruying Fan; Guomei Zhang; Lingzhi Shangguan; Jianbin Chao; Shaomin Shuang; Chuan Dong; Martin M F CHOI

doi:10.1016/j.aca.2009.02.046

Study of the contact charge transfer behavior between cryptophanes (A and E) and fullerene by absorption, fluorescence and ¹H NMR spectroscopy

Caihong Zhang, Weili Shen, Ruying Fan, Guomei Zhang, Lingzhi Shangguan, Jianbin Chao, Shaomin Shuang, Chuan Dong^*, Martin M F CHOI

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

6 Citations (Scopus)

Abstract

A group of novel cage-like compounds cryptophanes A and E were synthesized from vanillin by a three-step method. The intermolecular interaction between cryptophanes (A and E) and fullerene (C₆₀) was investigated in detail by absorption, fluorescence and ¹H NMR spectroscopy. The absorption of C₆₀ at 410-650 nm decreased in the presence of cryptophanes A or E. The decrease in absorption intensity was proportional to the concentration of cryptophanes A or E. On the other hand, the fluorescence intensity of cryptophanes A or E decreased and the emission maxima were blue-shifted with the increase in C₆₀ concentration. These results suggest that contact charge transfer (CCT) complexes can be formed from C₆₀ with cryptophanes A or E. In addition, the electrochemical behavior of cryptophanes (A and E) and C₆₀ was studied by cyclic voltammetry. The redox currents of cryptophanes (A and E) decreased and the peak potentials were shifted on addition of C₆₀. The changes in the chemical shifts (Δδ) of aromatic protons of cryptophanes (A and E) in their NMR spectra further support that CCT complexes were formed with cryptophanes as the electron donors and C₆₀ as the electron acceptor.

Original language	English
Pages (from-to)	118-123
Number of pages	6
Journal	Analytica Chimica Acta
Volume	650
Issue number	1
DOIs	https://doi.org/10.1016/j.aca.2009.02.046
Publication status	Published - 14 Sept 2009

Scopus Subject Areas

Analytical Chemistry
Biochemistry
Environmental Chemistry
Spectroscopy

User-Defined Keywords

Absorption
Contact-pair charge transfer
Cryptophane
Fullerene

Access to Document

10.1016/j.aca.2009.02.046

Cite this

@article{98d93508721446cc9b0febcfb2e7425c,

title = "Study of the contact charge transfer behavior between cryptophanes (A and E) and fullerene by absorption, fluorescence and 1H NMR spectroscopy",

abstract = "A group of novel cage-like compounds cryptophanes A and E were synthesized from vanillin by a three-step method. The intermolecular interaction between cryptophanes (A and E) and fullerene (C60) was investigated in detail by absorption, fluorescence and 1H NMR spectroscopy. The absorption of C60 at 410-650 nm decreased in the presence of cryptophanes A or E. The decrease in absorption intensity was proportional to the concentration of cryptophanes A or E. On the other hand, the fluorescence intensity of cryptophanes A or E decreased and the emission maxima were blue-shifted with the increase in C60 concentration. These results suggest that contact charge transfer (CCT) complexes can be formed from C60 with cryptophanes A or E. In addition, the electrochemical behavior of cryptophanes (A and E) and C60 was studied by cyclic voltammetry. The redox currents of cryptophanes (A and E) decreased and the peak potentials were shifted on addition of C60. The changes in the chemical shifts (Δδ) of aromatic protons of cryptophanes (A and E) in their NMR spectra further support that CCT complexes were formed with cryptophanes as the electron donors and C60 as the electron acceptor.",

keywords = "Absorption, Contact-pair charge transfer, Cryptophane, Fullerene",

author = "Caihong Zhang and Weili Shen and Ruying Fan and Guomei Zhang and Lingzhi Shangguan and Jianbin Chao and Shaomin Shuang and Chuan Dong and CHOI, {Martin M F}",

note = "Funding Information: The work described in this paper was supported by the National Nature Science Foundation Key Project (no. 50534100), the Youth Science Foundation of Shanxi Province (nos. 2007021007 and 2008021011).",

year = "2009",

month = sep,

day = "14",

doi = "10.1016/j.aca.2009.02.046",

language = "English",

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T1 - Study of the contact charge transfer behavior between cryptophanes (A and E) and fullerene by absorption, fluorescence and 1H NMR spectroscopy

AU - Zhang, Caihong

AU - Shen, Weili

AU - Fan, Ruying

AU - Zhang, Guomei

AU - Shangguan, Lingzhi

AU - Chao, Jianbin

AU - Shuang, Shaomin

AU - Dong, Chuan

AU - CHOI, Martin M F

N1 - Funding Information: The work described in this paper was supported by the National Nature Science Foundation Key Project (no. 50534100), the Youth Science Foundation of Shanxi Province (nos. 2007021007 and 2008021011).

PY - 2009/9/14

Y1 - 2009/9/14

N2 - A group of novel cage-like compounds cryptophanes A and E were synthesized from vanillin by a three-step method. The intermolecular interaction between cryptophanes (A and E) and fullerene (C60) was investigated in detail by absorption, fluorescence and 1H NMR spectroscopy. The absorption of C60 at 410-650 nm decreased in the presence of cryptophanes A or E. The decrease in absorption intensity was proportional to the concentration of cryptophanes A or E. On the other hand, the fluorescence intensity of cryptophanes A or E decreased and the emission maxima were blue-shifted with the increase in C60 concentration. These results suggest that contact charge transfer (CCT) complexes can be formed from C60 with cryptophanes A or E. In addition, the electrochemical behavior of cryptophanes (A and E) and C60 was studied by cyclic voltammetry. The redox currents of cryptophanes (A and E) decreased and the peak potentials were shifted on addition of C60. The changes in the chemical shifts (Δδ) of aromatic protons of cryptophanes (A and E) in their NMR spectra further support that CCT complexes were formed with cryptophanes as the electron donors and C60 as the electron acceptor.

AB - A group of novel cage-like compounds cryptophanes A and E were synthesized from vanillin by a three-step method. The intermolecular interaction between cryptophanes (A and E) and fullerene (C60) was investigated in detail by absorption, fluorescence and 1H NMR spectroscopy. The absorption of C60 at 410-650 nm decreased in the presence of cryptophanes A or E. The decrease in absorption intensity was proportional to the concentration of cryptophanes A or E. On the other hand, the fluorescence intensity of cryptophanes A or E decreased and the emission maxima were blue-shifted with the increase in C60 concentration. These results suggest that contact charge transfer (CCT) complexes can be formed from C60 with cryptophanes A or E. In addition, the electrochemical behavior of cryptophanes (A and E) and C60 was studied by cyclic voltammetry. The redox currents of cryptophanes (A and E) decreased and the peak potentials were shifted on addition of C60. The changes in the chemical shifts (Δδ) of aromatic protons of cryptophanes (A and E) in their NMR spectra further support that CCT complexes were formed with cryptophanes as the electron donors and C60 as the electron acceptor.

KW - Absorption

KW - Contact-pair charge transfer

KW - Cryptophane

KW - Fullerene

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