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

Bonifazi, Davide, Đorđević, Luka, Marangoni, Tomas, De Leo, Federica, Papagiannouli, Irini, Aloukos, Panagiotis, Couris, Stelios, Pavoni, Eleonora, Monti, Fillippo, Armaroli, Nicola and Prato, Maurizio 2016. [60]Fullerene-porphyrin [n]pseudorotaxanes: self-assembly, photophysics and third-order NLO responses. Physical Chemistry Chemical Physics -Cambridge- Royal Society of Chemistry 18 , pp. 11858-11868. 10.1039/C5CP06055A

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By means of different spectroscopic techniques, we investigate a novel series of free base 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 (NLO) response of these supramolecular systems showed that individual porphyrin and fullerene derivatives exhibit significantly lower second hyperpolarizability values when compared to their pseudorotaxanes functionalized 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.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Subjects: Q Science > QC Physics
Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1463-9076
Date of Acceptance: 5 January 2016
Last Modified: 04 Jun 2017 08:40

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