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Issue 16, 2017
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Porphyrin stacks as an efficient molecular glue to induce chirality in hetero-component calixarene–porphyrin assemblies

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Abstract

Tritopic tris-calix[4]arene TC4 – possessing three divergent cavities linked to a tris-aminophenylamine core – forms, in the presence of tetra-anionic Cu(II) porphyrins CuTPPS or a combination of different metallo-porphyrins (CuTPPS, NiTPPS and MnTPPS), discrete 3 : 1 porphyrin/tris-calixarene complexes. The 3 : 1-(CuTPPS/TC4) complex in particular is shown to be a key building block for the assembly of supramolecular architectures of increasing complexity. Directional (radial vs. stacked) self-assembly of these nanostructures was achieved by alternate addition of selected hetero-components in a programmed fashion. Addition of TC4 and CuTPPS, in turn, leads to a radial growth of the assembly, whereas, addition of single-cavity calix[4]arene C4 stoppers followed by a CuTPPS topping, promotes a stacked growth. In the latter case, the use of chiral (R)- or (S)-C4 stoppers is seen to induce chirality in the whole assembly. Circular dichroism data ultimately suggest that porphyrin molecules located above/below the 3 : 1 core complex act as a “molecular glue”, by making the interaction between chiral calix[4]arenes (R)- or (S)-C4 and the achiral 3 : 1-(CuTPPS/TC4) complex stronger.

Graphical abstract: Porphyrin stacks as an efficient molecular glue to induce chirality in hetero-component calixarene–porphyrin assemblies

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Publication details

The article was received on 17 Mar 2017, accepted on 03 Jul 2017 and first published on 04 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ00890B
Citation: New J. Chem., 2017,41, 8078-8083
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    Porphyrin stacks as an efficient molecular glue to induce chirality in hetero-component calixarene–porphyrin assemblies

    A. D’Urso, N. Marino, M. Gaeta, M. S. Rizzo, D. A. Cristaldi, M. E. Fragalà, S. Pappalardo, G. Gattuso, A. Notti, M. F. Parisi, I. Pisagatti and R. Purrello, New J. Chem., 2017, 41, 8078
    DOI: 10.1039/C7NJ00890B

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