Precision Nanotube Mimics via Self-Assembly of Programmed Carbon Nanohoops

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Title: Precision Nanotube Mimics via Self-Assembly of Programmed Carbon Nanohoops
Authors: Van Raden, Jeff M. | Leonhardt, Erik J. | Zakharov, Lev N. | Pérez-Guardiola, Andrés | Pérez-Jiménez, Ángel J. | Marshall, Checkers R. | Brozek, Carl K. | Sancho-Garcia, Juan-Carlos | Jasti, Ramesh
Research Group/s: Química Cuántica
Center, Department or Service: Universidad de Alicante. Departamento de Química Física
Keywords: Precision nanotube mimics | Self-assembly | Carbon nanohoops
Knowledge Area: Química Física
Issue Date: 17-Oct-2019
Publisher: American Chemical Society
Citation: The Journal of Organic Chemistry. 2020, 85(1): 129-141. doi:10.1021/acs.joc.9b02340
Abstract: The scalable production of homogeneous, uniform carbon nanomaterials represents a key synthetic challenge for contemporary organic synthesis as nearly all current fabrication methods provide heterogeneous mixtures of various carbonized products. For carbon nanotubes (CNTs) in particular, the inability to access structures with specific diameters or chiralities severely limits their potential applications. Here, we present a general approach to access solid-state CNT mimic structures via the self-assembly of fluorinated nanohoops, which can be synthesized in a scalable, size-selective fashion. X-ray crystallography reveals that these CNT mimics exhibit uniform channel diameters that are precisely defined by the diameter of their nanohoop constituents, which self-assemble in a tubular fashion via a combination of arene-pefluoroarene and C–H—F interactions. The nanotube-like assembly of these systems results in capabilities such as linear guest alignment and accessible channels, both of which are observed in CNTs but not in the analogous all-hydrocarbon nanohoop systems. Calculations suggest that the organofluorine interactions observed in the crystal structure are indeed critical in the self-assembly and robustness of the CNT mimic systems. This work establishes the self-assembly of carbon nanohoops via weak interactions as an attractive means to generate solid-state materials that mimic carbon nanotubes, importantly with the unparalleled tunability enabled by organic synthesis.
Sponsor: The synthesis and structural analysis of 2 and 3 were supported by the National Science Foundation (NSF) under grant numbers CHE-1808791 and CHE-1800586. A.J.P.J. and J.C.S.G. acknowledge the project AICO/2018/175 from the Regional Government (GVA/FSE).
URI: http://hdl.handle.net/10045/101194
ISSN: 0022-3263 (Print) | 1520-6904 (Online)
DOI: 10.1021/acs.joc.9b02340
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 American Chemical Society
Peer Review: si
Publisher version: https://doi.org/10.1021/acs.joc.9b02340
Appears in Collections:INV - QC - Artículos de Revistas

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