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Fluoro_CPP_050319.pdf (99.52 MB)

Precision Nanotube Mimics via Self-Assembly of Programmed Carbon Nanohoops

submitted on 03.05.2019, 20:00 and posted on 06.05.2019, 17:06 by Jeff M. Van Raden, Erik Leonhardt, Lev N. Zakharov, Andrés Pérez-Guardiola, Angel Jose Perez Jimenez, Checkers R. Marshall, Carl K. Brozek, Juan-Carlos Sancho-Garcia, Ramesh Jasti
The scalable production of homogenous, uniform carbon nanomaterials represents a key synthetic challenge for contemporary organic synthesis as nearly all current fabrication methods provide heterogenous 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 permanently 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.


Email Address of Submitting Author


University of Oregon


United States of America

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest