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 f="#poc3601-eo-0010" rel="references:#poc3601-eo-0010 #poc3601-eo-0011">. The compounds were characterized by means of NMR, UV–Vis spectroscopy, and X-ray crystallography. The electrochemical behavior was also investigated. The fulleropyrazoline f="#poc3601-eo-0010" rel="references:#poc3601-eo-0010"> exhibits anodically shifted reduction potentials of about 100 mV when compared with those for C₆₀, whereas f="#poc3601-eo-0011" rel="references:#poc3601-eo-0011"> exhibits cathodic shifts relative to pristine C₆₀. The complexation reaction of f="#poc3601-eo-0011" rel="references:#poc3601-eo-0011"> 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