Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

✍ Scribed by Leena Nebhani; Christopher Barner-Kowollik

• Book ID: 102495676
• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 314 KB
• Volume: 31
• Category: Article
• ISSN: 1022-1336
• DOI: 10.1002/marc.201000142

✦ Synopsis

Abstract

Cyclopentadienyl (Cp) capped polymers [polyethylene glycols (PEGs), $\overline M _{\rm n}$ = 2 000 g · mol^−1^], react readily with fullerenes in a 1:1 molar ratio (relative to the amount of fullerenes and Cp‐end groups) at ambient temperature within 5 min in the absence of any catalyst in a Diels–Alder (DA) reaction to provide fullerene‐PEG hybrids. Similarly, anthracenyl capped PEGs react with fullerenes (in a 1:3 molar ratio) in DA reactions to yield the corresponding hybrids, albeit over a period of 1.5 h at 80 °C and a lesser conversion. The efficiency of the transformation is monitored via electrospray ionization mass spectrometry (ESI‐MS), demonstrating that the fullerenes can be transformed into polymer hybrids; most efficiently when Cp‐functional polymer is used as the diene. In addition, the obtained hybrids were subjected to UV/Vis as well as thermogravimetric analysis further underpinning the formation of mono‐substituted C~60~‐PEG hybrids [wt.‐%^exp^ 70 ± 5 (PEG), 30 ± 5 (C~60~), wt.‐%^theo^ 68 (PEG), 32 (C~60~)].

magnified image