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Light-Controlled Morphologies of Self-Assembled Triarylamine–Fullerene Conjugates

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    Light-Controlled Morphologies of Self-Assembled Triarylamine–Fullerene Conjugates
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    † SAMS Research Group, University of Strasbourg, Institut Charles Sadron, CNRS, 23 rue du Loess, BP 84087, Strasbourg 67034 Cedex 2, France
    ‡ Institut für Polymerchemie, Universität Stuttgart, Pfaffenwaldring 55, Stuttgart 70569, Germany
    *Address correspondence to [email protected]
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    ACS Nano

    Cite this: ACS Nano 2015, 9, 3, 2760–2772
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    https://doi.org/10.1021/nn506646m
    Published March 3, 2015
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    Abstract

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    A family of triarylamine–fullerene conjugates has been synthesized and shown to self-assemble upon light stimulation in chlorinated solvents. This light-induced process primarily involves excitation of triarylamine derivatives, which then oxidize and stack with their neutral counterparts to form charge transfer complexes in the form of p-conducting channels, while fullerenes are consequently enforced in coaxial n-conducting columnar arrangements. These supramolecular heterojunctions can be organized over very long distances in micrometric fibers when a controlled amount of photons is provided from a white light source to initiate the process. Surprisingly, when sunlight or UV light is used instead, the nanostructuration leads to monodisperse spherical objects due to the nature of the nucleation–growth process involved in the stacks formation. This control over the supramolecular morphology of organic self-assemblies using the nature of light is of general interest for the design of functional responsive materials.

    Copyright © 2015 American Chemical Society

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    Synthetic protocols for the synthesis of compounds 1–4, synthetic routes and protocols for compounds 8 and 9, characterization of all synthesized products, 1H NMR spectra of compounds 2–4 before and after white-light irradiation, UV–vis–NIR and fluorescence spectroscopy in toluene, vis–NIR and fluorescence kinetics measurements, supplementary AFM and TEM imaging, DLS and WAXS experiments, cyclic voltammetry in solution and DFT calculations. This material is available free of charge via the Internet at http://pubs.acs.org.

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    ACS Nano

    Cite this: ACS Nano 2015, 9, 3, 2760–2772
    Click to copy citationCitation copied!
    https://doi.org/10.1021/nn506646m
    Published March 3, 2015
    Copyright © 2015 American Chemical Society
    Request reuse permissions

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