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.

The regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented 1,2,4,17-(cis-3′) and 1,2,3,4,9,10-(“S”-shaped) addition patterns is achieved.

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A modified indium tin oxide (ITO) microelectrode detector integrated with a dual-channel polydimethylsiloxane (PDMS) microchip is proposed for in-channel amperometric detection in microchip electrophoresis (ME).