On the C₆₀ Fullerene Adduct with Pentacene: Synthesis and Stability

Abstract

C₆₀ fullerene and pentacene were reacted under mild conditions in toluene, yielding the monoadduct, which was characterized by electronic absorption and Fourier transform infrared (FT-IR) spectroscopy. The C₆₀/pentacene adduct was studied by thermogravimetric analysis and its experimental composition was found in line with the theory for a 1:1 molar adduct. The decomposition temperature of the C₆₀/pentacene monoadduct was found to be 404°C. The decomposition implies a retro Diels–Alder reaction, yielding back C₆₀, which was recognized by FT-IR spectroscopy, while pentacene underwent decomposition and vaporization at 404°C. When an equimolar mixture of C₆₀ and pentacene was heated in a differential scanning calorimeter in absence of solvents, the formation of monoadduct occurred at 380°C, but above 400°C it was decomposed back to reactants.

Keywords:

• C₆₀ fullerene
• pentacene, Diels–Alder adduct
• retro Diels–Alder
• FT-IR spectroscopy
• thermal stability

Funding

The present research work has been supported by grant AYA-2011-27754 of the Spanish Ministry of Economy and Competitiveness of the Spanish Ministerio de Ciencia e Innovacion.