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CarbonNanotubesConjugatedwithTriazole-BasedTetrathiafulvalene-TypeReceptorsfor C60Recognition

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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
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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