[2]Catenanes decorated with porphyrin and [60]fullerene groups: Design, convergent synthesis, and photoinduced processes
Megiatto JD, Schuster DI, Abwandner S, De Miguel Rojas G, Guldi DM (2010)
Publication Type: Journal article, Original article
Publication year: 2010
Journal
Original Authors: Megiatto Jr. J.D., Schuster D.I., Abwandner S., De Miguel Rojas G., Guldi D.M.
Publisher: American Chemical Society
Book Volume: 132
Pages Range: 3847-3861
Journal Issue: 11
DOI: 10.1021/ja910149f
Abstract
A new class of [2]catenanes containing zinc(II)-porphyrin (ZnP) and/or [60]fullerene (C) as appended groups has been prepared. A complete description of the convergent synthetic approach based on Cu(I) template methodology and "click" 1, 3-dipolar cycloaddition chemistry is described. This new electron donor-acceptor catenane family has been subjected to extensive spectroscopic, computational, electro-chemical and photophysical studies. H NMR spectroscopy and computational analysis have revealed that the ZnP-C-[2]catenane adopts an extended conformation with the chromophores as far as possible from each other. A detailed photophysical investigation has revealed that upon irradiation the ZnP singlet excited state initially transfers energy to the (phenanthroline)-Cu(I) complex core, producing a metal-to-ligand charge transfer (MLCT) excited state, which in tum transfers an electron to the C group, generating the ZnP-[Cu(phen)]-C charge-separated state. A further charge shift from the [Cu(phen) ] complex to the ZnP subunit, competitive with decay to the ground state, leads to the isoenergetic long distance ZnP -[Cu(phen)-C charge-separated radical pair state, which slowly decays back to the ground state on the microsecond time scale. The slow rate of back-electron transfer indicates that in this interlocked system, as in previously studied covalently linked ZnP-C hybrid materials, this process occurs in the Marcus-inverted region. © 2010 American Chemical Society.
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APA:
Megiatto, J.D., Schuster, D.I., Abwandner, S., De Miguel Rojas, G., & Guldi, D.M. (2010). [2]Catenanes decorated with porphyrin and [60]fullerene groups: Design, convergent synthesis, and photoinduced processes. Journal of the American Chemical Society, 132(11), 3847-3861. https://doi.org/10.1021/ja910149f
MLA:
Megiatto, Jackson D., et al. "[2]Catenanes decorated with porphyrin and [60]fullerene groups: Design, convergent synthesis, and photoinduced processes." Journal of the American Chemical Society 132.11 (2010): 3847-3861.
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