New pyrazolino and pyrrolidino[60]fullerenes: the introduction of the hydrazone moiety for the formation of metal complexes
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- 作者：Elkin L. Romero ; Andrea Cabrera-Espinoza ; Nathaly Ortiz-Peñ ; a ; Mó ; nica Soto-Monsalve ; Fabio Zuluaga ; Richard F. D'Vries and Manuel N. Chaur
- 刊名：Journal of Physical Organic Chemistry
- 出版年：2017
- 出版时间：February 2017
- 年：2017
- 卷：30
- 期：2
- 全文大小：284K
- ISSN：1099-1395
文摘
The [3 + 2] cycloaddition reaction of C60 with pyridine-derived hydrazones (acting as dipolar reagents) was successfully conducted resulting in fullerene derivatives . The compounds were characterized by means of NMR, UV–Vis spectroscopy, and X-ray crystallography. The electrochemical behavior was also investigated. The fulleropyrazoline exhibits anodically shifted reduction potentials of about 100 mV when compared with those for C60, whereas exhibits cathodic shifts relative to pristine C60. The complexation reaction of with metallic ions (Zn2+, Cd2+, and Fe2+) was achieved. Job and Benesi–Hildebrand analysis confirmed the formation of complexes with a molar ratio of 1:1 and binding constants between 2.26 × 105 and 1.59 × 105 M−1. Electrochemistry of these complexes showed a marked influence of the metal ion on the reduction potentials. Copyright