Fullerene derivatives incorporating phosphoramidous ylide and phosphoramidate: synthesis and property.
The reaction of dimethyl acetylenedicarboxylate (DMAD) with C(60) in the presence of hexamethylphosphorous triamide (HMPT) or hexaethylphosphorus triamide (HEPT) results in fullerene derivatives incorporating HMPT or HEPT ylides. The ylide derivatives exhibit unusual electronic absorptions in the visible region (435-660 nm), likely due to the presence of the ylide moiety. Electrochemical studies revealed that the first reductive potential of these compounds was more negative relative to those of both C(60) (DeltaE = 130 mV) and a simple Bingel adduct (DeltaE = 90 mV). A phosphoramidate side product, which resulted from the addition of HMPT or HEPT to C(60) followed by hydrolysis, exhibited a featureless absorption spectrum in the visible region and a more negative first reductive potential (DeltaE = 70 mV) relative to that of C(60).
Chen
Sheng-Yuan
SY
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan, ROC 30010.
Cheng
Rai-Long
RL
Tseng
Cheng-Kuo
CK
Lin
Ya-Shiuan
YS
Lai
Li-Hsiang
LH
Venkatachalam
Rajesh Kumar
RK
Chen
Yu-Chie
YC
Cheng
Chien-Hong
CH
Chuang
Shih-Ching
SC