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New pyrazolino and pyrrolidino[60]fullerenes: the introduction of the hydrazone moiety for the formation of metal complexes
Author(s) -
Romero Elkin L.,
CabreraEspinoza Andrea,
OrtizPeña Nathaly,
SotoMonsalve Mónica,
Zuluaga Fabio,
D'Vries Richard F.,
Chaur Manuel N.
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3601
Subject(s) - chemistry , fullerene , moiety , electrochemistry , metal , hydrazone , reagent , pyridine , metal ions in aqueous solution , cycloaddition , annulene , cyclic voltammetry , inorganic chemistry , crystallography , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , electrode , catalysis
The [3 + 2] cycloaddition reaction of C 60 with pyridine‐derived hydrazones (acting as dipolar reagents) was successfully conducted resulting in fullerene derivatives 5a , 5b . The compounds were characterized by means of NMR, UV–Vis spectroscopy, and X‐ray crystallography. The electrochemical behavior was also investigated. The fulleropyrazoline 5a exhibits anodically shifted reduction potentials of about 100 mV when compared with those for C 60 , whereas 5b exhibits cathodic shifts relative to pristine C 60 . The complexation reaction of 5b with metallic ions (Zn 2+ , Cd 2+ , and Fe 2+ ) 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 × 10 5 and 1.59 × 10 5 M −1 . Electrochemistry of these complexes showed a marked influence of the metal ion on the reduction potentials. Copyright © 2016 John Wiley & Sons, Ltd.