Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition

B Zhang; JM White; DJ Jones; WWH Wong

Journal article

Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition

B Zhang, JM White, DJ Jones, WWH Wong

Organic and Biomolecular Chemistry | ROYAL SOC CHEMISTRY | Published : 2015

DOI: 10.1039/c5ob01630d

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Abstract

The regioselective synthesis of fullerene multiadducts was achieved from commercially available reagents in one pot over two steps. The configuration of the isolated regioisomers was determined using various NMR methods, UV-vis spectroscopy and electrochemical analysis with the structure of one isomer confirmed by single crystal X-ray analysis. Interesting variation in regioselectivity was observed when different amino acid reagents were used in the reactions. Theoretical calculations and additional experiments, such as deuterium exchange, led to a proposed mechanism for the regioselective product formation.

University of Melbourne Researchers

Jonathan White Author

David Jones Author

Wallace Wong Author

Related Projects (4)

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

This work was made possible by support from the Australian Renewable Energy Agency which funds the project grants within the Australian Centre for Advanced Photovoltaics. WWHW is supported by an Australian Research Council Future Fellowship (FT130100500). Responsibility for the views, information, or advice herein is not accepted by the Australian Government. We thank Dr Lars Goerigk for providing advice on the DFT calculations.