Journal
RESEARCH
Volume 2020, Issue -, Pages -Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.34133/2020/2059190
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Funding
- National Natural Science Foundation of China [21572211, 51572254]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- National Key Research and Development Program of China Stem Cell and Translational Research [2017YFA0402800]
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With the recent advance in chemical modification of fullerenes, electrosynthesis has demonstrated increasing importance in regioselective synthesis of novel fullerene derivatives. Herein, we report successively regioselective synthesis of stable tetra-and hexafunctionalized [60]fullerene derivatives. The cycloaddition reaction of the electrochemically generated dianions from [60]fulleroindolines with phthaloyl chloride regioselectively affords 1,2,4,17-functionalized [60]fullerene derivatives with two attached ketone groups and a unique addition pattern, where the heterocycle is rearranged to a [5,6]-junction and the carbocycle is fused to an adjacent [6,6]-junction. This addition pattern is in sharp contrast with that of the previously reported biscycloadducts, where both cycles are appended to [6,6]-junctions. The obtained tetrafunctionalized compounds can be successively manipulated to 1,2,3,4,9,10-functionalized [60]fullerene derivatives with an intriguing S-shaped configuration via a novel electrochemical protonation. Importantly, the stability of tetrafunctionalized 60]fullerene products allows them to be applied in planar perovskite solar cells as efficient electron transport layers.
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