Sonochemical Synthesis of Fullerene C60/Anthracene Diels-Alder Mono and Bis-adducts

The sonication of a mixture of C60 fullerene and anthracene in benzene yields the trans-1 bis-adduct C60(anthracene)2 in 52% yield. The bis-adduct is accompanied by the monoadduct C60(anthracene) in 26% yield. The reaction products of the sonochemical synthesis were identified by FT-IR and electronic absorption spectroscopy. The composition of adducts and their thermal stability was studied by thermogravimetric analysis (TGA) and by differential thermal analysis (DTA). The advantages of the sonochemical synthesis in terms of yields and regioselectivity toward the highly symmetric trans-1 bis-adduct C60(anthracene)2 are outlined.

[1]  E. Peeters,et al.  Carbonaceous molecules in the oxygen-rich circumstellar environment of binary post-AGB stars: ⋆ , 2011, 1110.5996.

[2]  D. A. García-Hernández,et al.  THE FORMATION OF FULLERENES: CLUES FROM NEW C60, C70, AND (POSSIBLE) PLANAR C24 DETECTIONS IN MAGELLANIC CLOUD PLANETARY NEBULAE , 2011, 1107.2595.

[3]  Jan Cami,et al.  Detection of C60 and C70 in a Young Planetary Nebula , 2010, Science.

[4]  A. Talyzin,et al.  High-temperature reactions of C60 with polycyclic aromatic hydrocarbons , 2010 .

[5]  I. Gitsov,et al.  Linear-dendritic supramolecular complexes as nanoscale reaction vessels for "green" chemistry. Diels-Alder reactions between fullerene C60 and polycyclic aromatic hydrocarbons in aqueous medium. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[6]  G. Miller,et al.  Scalable, Solution Phase Synthesis of the Trans‐1 Bisanthracene Adduct of [60]Fullerene , 2008 .

[7]  G. Miller,et al.  [60]Fullerene–acene chemistry: a review , 2006 .

[8]  Y. Murata,et al.  [60]Fullerene adducts with 9-substituted anthracenes: mechanochemical preparation and retro Diels–Alder reaction , 2005 .

[9]  M. Berberan-Santos,et al.  Kinetics of the Diels–Alder reaction between C60 and acenes , 2004 .

[10]  I. Trushkov,et al.  Cycloaddition to buckminsterfullerene C60: advancements and future prospects , 2002 .

[11]  M. Banerjee,et al.  Study of Molecular Complex Formation between [60]Fullerene and Two Series of Donors by the NMR Method , 2001 .

[12]  B. Kräutler,et al.  Regioselective `One‐Pot' Synthesis of Antipodal Bis‐adducts by Heating of Solid [5,6]Fullerene‐C60‐Ih and Anthracenes, Preliminary Communication , 2001 .

[13]  T. Müller,et al.  Efficient preparation of monoadducts of [60] fullerene and anthracenes by solution chemistry and their thermolytic decomposition in the solid state. , 2001, Chemistry.

[14]  Klaus Wurst,et al.  The Bis‐adducts of the [5,6]‐Fullerene C60 and Anthracene. , 2001 .

[15]  M. Saunders,et al.  Reversible Diels-Alder addition to fullerenes: a study of equilibria using (3)He NMR spectroscopy. , 2001, Journal of the American Chemical Society.

[16]  Y. Murata,et al.  The Solid-State Mechanochemical Reaction of Fullerene C60 , 1999 .

[17]  Y. Murata,et al.  Solid-State [4 + 2] Cycloaddition of Fullerene C(60) with Condensed Aromatics Using a High-Speed Vibration Milling Technique. , 1999, The Journal of organic chemistry.

[18]  R. Taylor,et al.  Lecture Notes on Fullerene Chemistry: A Handbook for Chemists , 1999 .

[19]  S. Fukuzumi,et al.  Solid state photochemistry for fullerene functionalization: Solid state photoinduced electron transfer in the Diels-Alder reaction with anthracenes , 1998 .

[20]  M. Ohashi,et al.  Spectral Characterization of Anthracene-, Cyclopentadiene-, and Dichlorocarbene-C60 Adducts , 1994 .

[21]  Y. Murata,et al.  Chemical Transformation of C60. Addition of Carbenes and Cycloaddition of Anthracene , 1993 .

[22]  M. Banerjee,et al.  Ground state EDA complex formation between [60]fullerene and a series of polynuclear aromatic hydrocarbons , 2000 .

[23]  P. Cruz,et al.  Fullerene chemistry under microwave irradiation , 2000 .

[24]  Śliwa Wanda Cycloaddition Reactions of Fullerenes , 1995 .

[25]  Y. Murata,et al.  Use of naphthalene as a solvent for selective formation of the 1:1 diels-alder adduct of C60 with anthracene , 1993 .

[26]  Hsien‐Hau Wang,et al.  Synthesis, purification, and characterization of the 1 : 1 addition product of C60 and anthracene , 1993 .