Regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns

• Published in: Chemical science (Cambridge) Vol. 11; no. 2; pp. 384 - 388
• Main Authors: Liu, Kai-Qing, Wang, Jun-Jie, Yan, Xing-Xing, Niu, Chuang, Wang, Guan-Wu
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 14.01.2020; Royal Society of Chemistry
• Subjects: Anions; Benzene; Chemistry; Chemistry, Multidisciplinary; Crystallography; Derivatives; Fluorescence; Fullerenes; NMR; Nuclear magnetic resonance; Physical Sciences; Protonation; Regioselectivity; Science & Technology; Single crystals; X ray analysis; FULLERENES; TETRAALLYLATION; REDUCTIVE BENZYLATION; REAGENTS; ADDUCTS; C-60; IMIDAZOLINE; WATER
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c9sc02131k

The efficient and regioselective electrosynthesis of tetra- and hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns has been achieved. The tetra-functionalized [60]fullerene derivative with an intriguing 1,2,4,17-addition pattern is regioselectively obtained by cyclization reaction of the dianionic species generated electrochemically from a [60]fulleroindoline with 1,2-bis(bromomethyl)benzene at 0 °C, and can be converted to the more stable 1,2,3,4-adduct at 25 °C. Furthermore, the hexa-functionalized [60]fullerene derivative with the 1,2,3,4,9,10-addition pattern displaying a unique " S "-shaped configuration can be synthesized by protonation of the electrochemically generated dianion of the obtained tetra-functionalized 1,2,4,17-adduct. The structures of the tetra- and hexa-functionalized products have been determined by spectroscopic data and single-crystal X-ray analysis. 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.