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Donor−Acceptor Phthalocyanine Nanoaggregates
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    Donor−Acceptor Phthalocyanine Nanoaggregates
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    Contribution from the Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain, and the Department of Organic Chemistry, NSRIM Center, University of Nijmegen, Toernooivel, 6525 ED Nijmegen, The Netherlands
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2003, 125, 40, 12300–12308
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    https://doi.org/10.1021/ja030038m
    Published September 11, 2003
    Copyright © 2003 American Chemical Society

    Abstract

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    A novel donor−acceptor bisphthalocyanine (bis-Pc, 1) in which two different Pc units (Zn(II)-Pc and Ni(II)-Pc) are linked via vinylene spacers to the pseudopara positions of a central [2.2]paracyclophane moiety is described. The synthesis of 1 is achieved by two successive Heck reactions of pseudopara-divinyl[2.2]paracyclophane 9 with, sequentially, a zinc(II)- and a nickel(II)-iodophthalocyanine (4 and 5, respectively). The self-assembly ability of 1, which is the result of the complementary donor−acceptor character of its phthalocyanine units, has been assessed by a variety of techniques. It is revealed that 1 forms one-dimensional aggregates of nanometer-sized dimension, whereas equimolar mixtures of the donor and acceptor Pc subunits 2 and 3, although strongly interacting, do not give large arrays. The aggregates of 1 represent a novel type of supramolecular polymers based mainly upon donor−acceptor interactions.

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     Universidad Autónoma de Madrid.

     University of Nijmegen.

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    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

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    Details on calculations of binding constants, 1H NMR spectra of compounds 1, 2, and 3, figures showing the temperature dependence of association for compound 1, and the UV−vis spectrum of bisphthalocyanine 1 obtained upon subtracting the absorption spectra of the reference molecules 2 and 3 showing both the aggregation and CT bands. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Published September 11, 2003
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