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[60]Fullerene as a substituent.

Alessandro Bagno1, Sofia Claeson, Michele Maggini

  • 1Centro Meccanismi CNR, Dipartimento di Chimica Organica, Università di Padova, Via Marzolo 1, 35131 Padua, Italy.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 14, 2002
PubMed
Summary

The fullerene group exhibits a mild electron-withdrawing effect and high hydrophobicity. Fulleropyrrolidine shows significantly reduced basicity and reactivity due to fullerene interactions.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • Fullerenes are unique carbon allotropes with diverse chemical properties.
  • Understanding substituent effects is crucial for designing functionalized fullerene derivatives.

Purpose of the Study:

  • To quantitatively assess the electronic and hydrophobic substituent effects of the dihydro[60]fullerenyl group.
  • To investigate the impact of the fullerene moiety on the acid-base properties and nucleophilicity of a fulleropyrrolidine.

Main Methods:

  • Determined Hammett sigma value using pK measurements of a fullerene-based benzoic acid via NMR spectroscopy.
  • Evaluated hydrophobicity parameter (pi) by comparing the fullerene derivative with a model compound.
  • Assessed acid-base properties and reactivity of fulleropyrrolidine and its model compound.

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Main Results:

  • The dihydro[60]fullerenyl group has a small electron-withdrawing effect (sigma = 0.06), primarily inductive.
  • The fullerene substituent imparts high hydrophobicity (pi > 3).
  • Fulleropyrrolidine exhibits drastically reduced basicity (six orders of magnitude lower) and reactivity (1000 times lower) compared to its model.

Conclusions:

  • The electronic and hydrophobic characteristics of the fullerene substituent have been quantitatively defined.
  • The fullerene cage significantly modulates the chemical behavior of attached functional groups, likely through through-space electronic interactions.