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Handedness Enantioselection of Carbon Nanotubes Using Helical Assemblies of Flavin Mononucleotide

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2012, 134, 32, 13196-13199
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    Handedness Enantioselection of Carbon Nanotubes Using Helical Assemblies of Flavin Mononucleotide
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    ‡ † †Nanomaterials Optoelectronics Laboratory (NOEL), Polymer Program, Institute of Materials Science and ‡Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3136, United States
    [email protected]
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2012, 134, 32, 13196–13199
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    https://doi.org/10.1021/ja305250g
    Published August 7, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    In order to truly unlock advanced applications of single-walled carbon nanotubes (SWNTs), one needs to separate them according to both chirality and handedness. Here we show that the chiral d-ribityl phosphate chain of flavin mononucleotide (FMN) induces a right-handed helix that enriches the left-handed SWNTs for all suspended (n,m) species. Such enantioselectivity stems from the sp3 hybridization of the N atom anchoring the sugar moiety to the flavin ring. This produces two FMN conformations (syn and anti) analogous to DNA. Electrostatic interactions between the neighboring uracil moiety and the 2′-OH group of the side chain provide greater stability to the anti-FMN conformation that leads to a right-handed FMN helix. The right-handed twist that the FMN helix imposes to the underlying nanotube, similar to “Indian burn”, causes diameter dilation of only the left-handed SWNTs, whose improved intermolecular interactions with the overlaying FMN helix, impart enantioselection.

    Copyright © 2012 American Chemical Society

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    Methods, UV–vis–NIR, PLE maps, RRS, and molecular mechanics analysis. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 40 publications.

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    Cite this: J. Am. Chem. Soc. 2012, 134, 32, 13196–13199
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja305250g
    Published August 7, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

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