Synthesis of fullerene adducts with terpyridyl- or pyridylpyrrolidine groups in trans-1 positions.
Two C(60) hexakis-adducts (2 and 3) were synthesized by using a protection-deprotection strategy. The symmetric fullerene tetrakis-adduct 8 was obtained by anthracene removal from the hexakis-adduct 7. Reaction of 8 with terpyridylglycine or pyridylglycine afforded two hexakis-adducts, 2 and 3. By using the retro-cyclopropanation reaction, the four malonate addends located on the equatorial belt of the hexakis-adducts were removed to afford two trans-1 bis-adducts, 4 and 5, with terpyridyl- or pyridylpyrrolidine groups. The structures of 2 and 3 were confirmed by matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, and (1)H, (13)C, and COSY NMR, and UV-visible spectroscopy. The cyclic voltammograms of fullerene multiadducts 2, 3, and 9 show irreversible reductions. Self-assembled monolayers (SAMs) of 1 and 3 were formed on gold surfaces through nitrogen adsorption. SAMs of 3 represent the first example of a fullerene hexakis-adduct formed on gold surfaces through nitrogen adsorption. Controlled potential electrolyses (CPE) were conducted to prepare trans-1 bis-adducts 4 and 5 modified with terpyridyl and pyridyl groups.
Zhang
Sheng
S
Department of Chemistry, Clemson University, Clemson, SC 29634, USA.
Lukoyanova
Olena
O
Echegoyen
Luis
L
D004563:Electrochemistry; D037741:Fullerenes / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011725:Pyridines / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet
D037741:Fullerenes; D011725:Pyridines; D011759:Pyrrolidines; D005998:Glycine