Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 23, Pages 7502-7508Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03768
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Funding
- NSF [DMR-1205302, CHE-1408865, DMR-1157490, CHE-1305125]
- Robert A. Welch Foundation [AH-0033]
- State of Florida
- Office of Science, Office of Basic Energy Sciences of the U.S. Department of Energy [DE-AC02-05CH11231]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1305125, 1408865] Funding Source: National Science Foundation
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1205302] Funding Source: National Science Foundation
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The regioselective synthesis of easily isolable pure bismethano derivatives of C-60 and C-70 with high steric congestion is described using 1,3-dibenzoylpropane bis-p-toluenesulfonyl hydrazone as the addend precursor. When the addition occurs at two [6,6] ring junctions within the same hexagon, bisadducts with mirror symmetry are obtained for both C-60 and C-70. When the addition occurs at two [5,6] ring junctions in C-60, a symmetrical adduct is formed, which readily undergoes photo-oxygenation and ring opening to yield a fullerene with a hole in the cage. In this work, we also propose a simple and general system to name all of the possible [6,6] bisadduct isomers on C-70.
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