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Mateos Gil, Jaime and Calbo, Joaquín and Rodríguez Perez, Laura and Herranz, M.Angeles and Ortí, Enrique and Martín, Nazario (2019) CarbonNanotubesConjugatedwithTriazole-BasedTetrathiafulvalene-TypeReceptorsfor C60Recognition. ChemPlusChem, 84 . pp. 730-739. ISSN 2192-6506
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Official URL: https://onlinelibrary.wiley.com/doi/epdf/10.1002/cplu.201900078
Abstract
Fullerene receptors prepared by a twofold CuI -catalyzed azide-alkyne cycloaddition (CuAAC) reaction with -extended tetrathiafulvalene (exTTF) have been covalently linked to singlewalled carbon nanotubes (SWCNTs) and multi-walled carbon nanotubes (MWCNTs). The nanoconjugates obtained were characterized by several analytical, spectroscopic and microscopic techniques (TEM, FTIR, Raman, TGA and XPS), and evaluated as C60 receptors by UV-Vis spectroscopy. The complexation between the exTTF-triazole receptor in the free state and C60 was also studied by UV-Vis and 1 H NMR titrations, and compared with analogous triazole-based tweezer-type receptors containing the electron-acceptor 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) and benzene rings instead of exTTF motifs, providing in all cases very similar values for the association constant (log Ka 3.0‒3.1). Theoretical density functional theory (DFT) calculations demonstrated that the enhanced interaction between the host and the guest upon increasing the size of the -conjugated arms of the tweezer is compensated by an increase in the energy penalty needed to distort the geometry of the host to wrap C60.
Item Type: | Article |
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Uncontrolled Keywords: | carbonnanotubes·densityfunctionalcalculations·fullerenes·host-guestinteractions·π-extendedtetrathiafulvalenes |
Subjects: | Sciences > Chemistry > Chemistry, Organic |
ID Code: | 58514 |
Deposited On: | 13 Jan 2020 15:51 |
Last Modified: | 13 Jan 2020 15:55 |
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