Study of the contact charge transfer behavior between cryptophanes (A and E) and fullerene by absorption, fluorescence and 1H NMR spectroscopy.
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 (C(60)) was investigated in detail by absorption, fluorescence and (1)H NMR spectroscopy. The absorption of C(60) 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 C(60) concentration. These results suggest that contact charge transfer (CCT) complexes can be formed from C(60) with cryptophanes A or E. In addition, the electrochemical behavior of cryptophanes (A and E) and C(60) was studied by cyclic voltammetry. The redox currents of cryptophanes (A and E) decreased and the peak potentials were shifted on addition of C(60). The changes in the chemical shifts (Delta delta) 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 C(60) as the electron acceptor.
Zhang
Caihong
C
Research Center of Environmental Science and Engineering, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China.
Shen
Weili
W
Fan
Ruying
R
Zhang
Guomei
G
Shangguan
Lingzhi
L
Chao
Jianbin
J
Shuang
Shaomin
S
Dong
Chuan
C
Choi
Martin M F
MM
D000042:Absorption; D037741:Fullerenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D014230:Triazoles / Q000737:chemistry*
D037741:Fullerenes; D011083:Polycyclic Compounds; D014230:Triazoles; C523242:cryptophane; C545484:cryptophane A; C545485:cryptophane E