Sequence, stoichiometry, and dimensionality control in porphyrin/bis-calix[4]arene self-assemblies in aqueous solution

Chemistry : a European Journal
Alessandro D'UrsoRoberto Purrello

Abstract

The use of a water-soluble octacationic bis-calix[4]arene with divergent cavities (BC(4)) as a templating agent for the assembly of a tetraanionic porphyrin (CuTPPS) has allowed the noncovalent synthesis of 2D or 3D multiporphyrin assemblies. Self-assembly of CuTPPS and BC(4) molecules proceeded under hierarchical control in a stepwise fashion to yield discrete and isolable supramolecular nanostructures containing up to 33 molecular elements (i.e., the CuTPPS/BC(4) 17:16 assembly, obtained in less than three hours). The formation of these species could be conveniently monitored by means of UV/Vis spectroscopy by following the absorbance of the Soret band at 412 nm. In particular, the attainment of the pivotal CuTPPS/BC(4) 5:4 species with a cruciform structure, as the key fork-point intermediate for the subsequent formation of the higher 2D and 3D assemblies, has been demonstrated by light-scattering studies and by an unequivocal synthesis of mixed-porphyrin/calixarene 5:4 species involving the use of two different types of metallated porphyrins, namely CuTPPS and MnTPPS. The remarkable stability of these assemblies permits a stepwise synthesis that makes it possible to choose the desired porphyrin sequence.

References

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Citations

May 23, 2015·Organic & Biomolecular Chemistry·Lucia BarberaValentina Villari
Oct 11, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mickey VinodhTalal F Al-Azemi
Nov 11, 2017·Chemistry : a European Journal·Nadia ManganaroGiuseppe Gattuso
Mar 13, 2012·Chemistry : a European Journal·Hai QianYu Liu
Jun 14, 2012·Chemical Communications : Chem Comm·Alessandro D'UrsoRoberto Purrello
May 24, 2012·Chemical Society Reviews·Dong-Sheng Guo, Yu Liu
Jan 29, 2020·Chemistry : a European Journal·Massimiliano GaetaRoberto Purrello
Mar 21, 2012·Chemical Communications : Chem Comm·Alessandro D'UrsoRoberto Purrello
Oct 20, 2012·Chemical Communications : Chem Comm·Hong-Xia ZhaoYu Liu
Feb 13, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Massimiliano GaetaAlessandro D'Urso
Apr 18, 2012·The Journal of Physical Chemistry. B·Valentina VillariNorberto Micali

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