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Fullerene lipids: Synthesis of novel nitrogen‐bridged [60]fullerene fatty ester derivatives
Author(s) -
Lie Ken Jie Marcel S. F.,
Cheung Sunny W. H.,
Ho Janette C. M.
Publication year - 2001
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-001-0738-0
Subject(s) - fullerene , fullerene chemistry , aziridine , yield (engineering) , chemistry , derivative (finance) , toluene , nitrogen , organic chemistry , materials science , ring (chemistry) , economics , financial economics , metallurgy
Reactions of methyl 6‐azido‐hexanoate, 8‐azido‐octanoate, and 12‐azido‐dodecanoate with [60]fullerene ( 1 ) gave the corresponding aza‐[60]fullerene ester derivatives ( 2a‐2c , 22–35% based on the amount of [60]fullerene reacted). The nitrogen atom is bonded to the [60]fullerene cage to yield a “[5,6]‐open” type aza substructure. This was confirmed by the appearance of 30–31 sp 2 signals at δ C 133–147 in the carbon nuclear magnetic resonance spectra. Reaction of methyl 11‐azido‐7‐undecynoate with [60]fullerene furnished a mixture of aza‐[60]fullerene ( 2d , 53%) and aziridine‐[60]fullerene ( 2e , 38%) ester derivatives. Compound 2e was identified as the “[6,6]‐closed” type aziridine‐[60]fullerene derivative, which displayed 10 sp 2 signals in the region δ C 140–145 and one signal at δ C 85.05 for the sp 3 carbons of the cage. Refluxing a solution of compound 2d in toluene for 50 h gave about 50% yield of compound 2e , but not vice versa.