Issue 17, 2016

[60]Fullerene–porphyrin [n]pseudorotaxanes: self-assembly, photophysics and third-order NLO response

Abstract

By means of different spectroscopic techniques, we investigate a novel series of porphyrin derivatives (H2TPP), connected to dibenzo-24-crown-8 (DB24C8) moieties, which undergo self-assembly with different methano[60]fullerene units bearing dibenzylammonium (DBA) cations. The formation of both [2] and [3]pseudorotaxanes was proved by means of NMR, UV-Vis-NIR absorption and emission spectroscopies. With the support of molecular modelling studies, spectroscopic investigations showed the presence of a secondary interaction between the porphyrin and the C60 chromophores leading to the formation of different types of “face-to-face” assemblies. Remarkably, investigations of the non-linear optical response of these supramolecular systems showed that individual porphyrin and fullerene derivatives exhibit significantly lower second hyperpolarizability values when compared to their pseudorotaxanes functionalised counterparts. This proves that this class of supramolecular materials possesses relevant NLO response, which strongly depends on the structural arrangement of the chromophores in solution.

Graphical abstract: [60]Fullerene–porphyrin [n]pseudorotaxanes: self-assembly, photophysics and third-order NLO response

Supplementary files

Article information

Article type
Paper
Submitted
08 Oct 2015
Accepted
05 Jan 2016
First published
08 Jan 2016

Phys. Chem. Chem. Phys., 2016,18, 11858-11868

Author version available

[60]Fullerene–porphyrin [n]pseudorotaxanes: self-assembly, photophysics and third-order NLO response

L. Đorđević, T. Marangoni, F. De Leo, I. Papagiannouli, P. Aloukos, S. Couris, E. Pavoni, F. Monti, N. Armaroli, M. Prato and D. Bonifazi, Phys. Chem. Chem. Phys., 2016, 18, 11858 DOI: 10.1039/C5CP06055A

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