Friday, 6 October 2006 - 9:00 AM
Great Hall (Christ Episcopal Church)
197

A Selective, Solution Phase Approach to the Trans-1 Bisanthracene Adduct of [60]Fullerene

Wenling Jia, University of New Hampshire, Durham, NH and Glen P. Miller, University of New Hampshire, Durham, NH.

The antipodal (trans-1) bisanthracene adduct of [60]fullerene has been prepared in a highly regioselective, solution phase reaction. Thus, upon heating [60]fullerene with an excess of 9,10-dihydroanthracene in the presence of 2,3-dichloro-4,5-dicyanobenzoquinone (DDQ) in toluene at 90 -110°C, the trans-1 bisanthracene adduct of [60]fullerene forms in good yield. The only other fullerene product detected in significant quantity is the well known [60]fullerene-anthracene monoadduct which is readily separated via silica chromatography. Other bisanthracene adducts are occasionally detected but always in very low yield. For comparison, similar reactions were carried out with an excess of anthracene in refluxing toluene, resulting in a mixture of 7 different bisanthracene adducts, the trans-1 adduct produced in lowest yield. The mechanism for the 9,10-dihydroanthracene reaction leading to trans-1 product is under investigation. Utilizing either lower (50 - 60°C) or higher (~180°C) temperatures destroys the regioselectivity and gives complex mixtures of numerous bisanthracene adducts. Control experiments have ruled out low solubility of the trans-1 bisanthracene adduct as a controlling factor.


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