Langmuir Monolayers of an Inclusion Complex Formed by a New Calixarene Derivative and Fullerene

The design of new molecules with directed interactions to functional molecules as complementary building blocks is one of the main goals of supramolecular chemistry. A new p-tert-butylcalix[6]arene monosubstituted derivative bearing only one alkyl chain with an acid group (C6A3C) has been synthesize...

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Bibliographic Details
Published in:Langmuir 2012-08, Vol.28 (33), p.12114-12121
Main Authors: González-Delgado, Antonio M, Giner-Casares, Juan J, Brezesinski, Gerald, Regnouf-de-Vains, Jean-Bernard, Camacho, Luis
Format: Article
Language:English
Subjects:
Air
Calixarenes - chemistry
Chemistry
Cross-disciplinary physics: materials science
rheology
Exact sciences and technology
Fullerenes - chemistry
Fullerenes and related materials
diamonds, graphite
General and physical chemistry
Materials science
Microscopy
Models, Molecular
Molecular Conformation
Physics
Specific materials
Surface Properties
Water - chemistry
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Summary:The design of new molecules with directed interactions to functional molecules as complementary building blocks is one of the main goals of supramolecular chemistry. A new p-tert-butylcalix[6]arene monosubstituted derivative bearing only one alkyl chain with an acid group (C6A3C) has been synthesized. The C6A3C has been successfully used for building Langmuir monolayers at the air–water interface. The C6A3C molecule adopts a flatlike orientation with respect to the air–water interface. The molecular structure gives the molecule amphiphilic character, while allowing the control of both the dissociation degree and the molecular conformation at the air–water interface. The C63AC has been combined with pristine fullerene (C60) to form the supramolecular complex C6A3C:C60 in 2:1 molar ratio (CFC). The CFC complex retains the ability of C6A3C to form Langmuir monolayers at the air/water interface. The interfacial molecular arrangement of the CFC complex has been convincingly described by in situ UV–vis reflection spectroscopy and synchrotron X-ray reflectivity measurements. Computer simulations complement the experimental data, confirming a perpendicular orientation of the calixarene units of CFC with respect to the air–water interface. This orientation is stabilized by the formation of intermolecular H-bonds. The interfacial monolayer of the CFC supramolecular complex is proposed as a useful model for the well-defined self-assembly of recognition and functional building blocks.
ISSN:0743-7463
1520-5827
DOI:10.1021/la302440g