Fullerene derivatives incorporating phosphoramidous ylide and phosphoramidate: Synthesis and property

Sheng Yuan Chen, Rai Long Cheng, Cheng Kuo Tseng, Ya Shiuan Lin, Li Hsiang Lai, Rajesh Kumar Venkatachalam, Yu-Chie Chen, Chien Hong Cheng, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

(Chemical Equation Presented) The reaction of dimethyl acetylenedicarboxylate (DMAD) with C60 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 C60 (ΔE = 130 mV) and a simple Bingel adduct (ΔE = 90 mV). A phosphoramidate side product, which resulted from the addition of HMPT or HEPT to C60 followed by hydrolysis, exhibited a featureless absorption spectrum in the visible region and a more negative first reductive potential (ΔE ) 70 mV) relative to that of C60.

Original languageEnglish
Pages (from-to)4866-4869
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number13
DOIs
StatePublished - 3 Jul 2009

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    Chen, S. Y., Cheng, R. L., Tseng, C. K., Lin, Y. S., Lai, L. H., Venkatachalam, R. K., Chen, Y-C., Cheng, C. H., & Chuang, S-C. (2009). Fullerene derivatives incorporating phosphoramidous ylide and phosphoramidate: Synthesis and property. Journal of Organic Chemistry, 74(13), 4866-4869. https://doi.org/10.1021/jo8026017