Abstract
Molecular self-assembly is considered as a promising way to control the manufacture of new materials and their integration into hybrid devices with novel properties. In this work we have synthesized a fulleropyrrolidine bearing a phenylacetylene moiety via the Prato reaction. The characterization of the fulleropyrrolidine by nuclear magnetic resonance and optical spectroscopy is reported, and its self-assembly by crystallization study has been investigated according to the used solvents. If the solvent that effectively solubilizes fullerene derivative is tetrahydrofurane, the nano-square plates with 1–3 μm in length and 50–100 nm in thickness are formed, while if the solvent is toluene, 5 μm diameter ‘nano-flowers’ are obtained.
Highlights
During the last fifteen years, fullerene-based supramolecular assemblies have been extensively investigated
C60 is a highly hydrophobic molecule with a perfect icosahedral symmetry. It possesses exceptional photophysical properties and low reorganization energy [1]. All these properties make fullerene an ideal candidate for a large number of applications such as solar cells [2, 3], organic light-emitting diode (OLED) [4], organic field-effect transistor (OFET) [5, 6]
In this paper we explore the self-assembling properties of a fulleropyrrolidine functionalized with a phenylacetylene moiety via the Prato reaction
Summary
During the last fifteen years, fullerene-based supramolecular assemblies have been extensively investigated. By using classical covalent functionalization to make more sophisticated C60 structures, the size, order, and complexity of the supramolecular assemblies continuously increased This method has led to, for example, fullerenebased micelles, vesicles, and aggregates [8,9,10,11,12,13,14,15,16,17,18], polymers [19,20,21,22,23,24,25], and liquid crystals [26,27,28,29,30,31,32,33,34,35], as well as the organization of fullerene on electrode or nanoparticle surfaces [36,37,38]. The characterization of this compound by nuclear magnetic resonance (NMR), optical spectroscopy, x-ray diffraction as well as microscopy allowed identifying the interactions that lead to self-assembly properties
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