Synlett 2016; 27(14): 2101-2104
DOI: 10.1055/s-0035-1562462
cluster
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Properties of a Buckybowl/Buckyball Dyad

Venkatachalam Rajeshkumar
a  School of Physical & Mathematical Sciences, Nanyang Technological University, 637371 Singapore, Singapore   Email: mstuparu@ntu.edu.sg
,
Courte Marc
a  School of Physical & Mathematical Sciences, Nanyang Technological University, 637371 Singapore, Singapore   Email: mstuparu@ntu.edu.sg
,
Denis Fichou
a  School of Physical & Mathematical Sciences, Nanyang Technological University, 637371 Singapore, Singapore   Email: mstuparu@ntu.edu.sg
b  Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, 75005 Paris, France
c  CNRS, UMR 8232, Institut Parisien de Chimie Moléculaire, 75005 Paris, France
,
Mihaiela C. Stuparu*
a  School of Physical & Mathematical Sciences, Nanyang Technological University, 637371 Singapore, Singapore   Email: mstuparu@ntu.edu.sg
d  School of Materials Science and Engineering, Nanyang Technological University, 637371, Singapore, Singapore
› Author Affiliations
Further Information

Publication History

Received: 05 May 2016

Accepted after revision: 15 June 2016

Publication Date:
05 July 2016 (online)


Abstract

In this work, we describe the synthesis of a molecule in which fullerene C60 is covalently attached to a bowl-shaped polycyclic aromatic hydrocarbon, corannulene. The developed synthetic route is comprised of four linear steps with isolated yields ranging from 41–91%. The first three steps relate to the preparation of a hydrazone derivative of corannulene carrying a butyric acid methyl ester group. This key compound generates a reactive diazo moiety under base-induced decomposition process. The generated diazoalkane then adds to the C60 molecule to furnish the targeted corannulene-C61-butyric acid methyl ester (CCBM) molecule. This compound is structurally characterized by NMR spectroscopy and mass spectrometry, whereas material properties are determined with the help of optical absorption spectroscopy and cyclic voltammetry. Finally, some preliminary aspects on its application are examined in a poly(3-hexyl thiophene)-based photovoltaic device.

Supporting Information

 
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