Regioselective electrosynthesis of rare 1,2,3,16-functionalized [60]fullerene derivatives

Yang Xiao; San-E Zhu; Ding-Jia Liu; Mitsuaki Suzuki; Xing Lu; Guan-Wu Wang

doi:10.1002/anie.201310565

Regioselective electrosynthesis of rare 1,2,3,16-functionalized [60]fullerene derivatives

Angew Chem Int Ed Engl. 2014 Mar 10;53(11):3006-10. doi: 10.1002/anie.201310565. Epub 2014 Feb 5.

Authors

Yang Xiao¹, San-E Zhu, Ding-Jia Liu, Mitsuaki Suzuki, Xing Lu, Guan-Wu Wang

Affiliation

¹ Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China).

PMID: 24500858
DOI: 10.1002/anie.201310565

Abstract

Fullerene derivatives with different addition patterns exhibit different physical, chemical, and biological properties, which are important for fullerene applications. Novel and rare 1,2,3,16-functionalized [60]fullerene derivatives having a five-membered heterocycle fused to a [5,6]-junction were obtained with high regioselectivity by electrochemical derivatization of a [60]fulleroindoline. The product structures were determined by spectroscopic data and single-crystal X-ray analysis. The obtained high regioselectivity was rationalized using theoretical calculations.

Keywords: electrochemistry; fullerenes; rearrangement; regioselectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Electrochemical Techniques
Fullerenes / chemistry*
Molecular Conformation
Sodium Compounds / chemistry
Stereoisomerism

Substances

Fullerenes
Sodium Compounds
sodium hydride