[structure: see text] Two types of covalently NH-linked porphyrin-phthalocyanine dyads, connected either through the meso phenyl group or the beta-pyrrolic position of the porphyrin, have been synthesized following statistical condensation methodologies for phthalocyanine preparation and palladium-catalyzed amination methods. Photophysical studies have revealed that energy transfer from the porphyrin to the phthalocyanine prevails regardless of linkage.
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Fullerene binding effects in Al(III)/Zn(II) Porphyrin/Phthalocyanine photophysical properties and charge transport.
Spectrochim Acta A Mol Biomol Spectrosc
March 2022
Laboratory of Theoretical Chemistry, Faculty of Chemistry and Biology, University of Santiago de Chile (USACH), 9170022, Santiago, Chile. Electronic address:
We evaluate the fullerene C binding effect; through the metal (Al) and through the ligand (Pc,TPP), on the photophysical and charge transport properties of M-porphyrin(TPP)/phthalocyanine(Pc) (M = Al(III), Zn(II)). We perform density functional theory (DFT) and time-dependent DFT calculations for the macrocycle-C dyads, showing that all systems studied are thermodynamically favorable. The C binding effect on the absorption spectrum is a red-shift of the Q and Soret (B) bands of TPPs and Pcs.
View Article and Find Full Text PDFSupramolecular donor-acceptor hybrids of porphyrins/phthalocyanines with fullerenes/carbon nanotubes: electron transfer, sensing, switching, and catalytic applications.
Chem Commun (Camb)
September 2009
Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051, USA.
Since the three-dimensional electron-accepting fullerene has been found to be an excellent building block for self-assembled supramolecular systems, we have investigated photoinduced electron transfer processes in supramolecular fullerene systems with porphyrins and phthalocyanines as electron donors to mimic natural photosynthesis. We have successfully formed self-assembled supramolecular dyads and triads via metal-ligand coordination, crown-ether inclusion, ion pairing, hydrogen-bonding, or pi-pi stacking interactions. Although the single mode of binding gives usually flexible supramolecular structures, the newly developed strategy of multiple modes of binding results in conjugates of defined distance and orientation between the donor and acceptor entities, which influences the overall electron transfer reactions.
View Article and Find Full Text PDFTandem cofacial stacks of porphyrin-phthalocyanine dyads through complementary coordination.
Chemistry
August 2008
Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192, Japan.
A novel straightforward methodology to organize discrete heterogeneous stacks of porphyrin and phthalocyanine employed an imidazolyl-to-zinc complementary coordination protocol for a Zn(II) phthalocyanine that contains an imidazolyl terminal with an ethynylporphyrin as a coplanar spacer. Structural elucidation was performed by means of size-exclusion chromatography, spectral titration, and NMR spectroscopy. The association constants for the complementary coordination of the heterogeneous slipped-cofacial tetrads reached extremely high values, in the order of 10(14) M(-1).
View Article and Find Full Text PDFSynthesis of novel N-linked porphyrin-phthalocyanine dyads.
Org Lett
April 2007
Universidade de Aveiro, Departamento de Química, Campus de Santiago, 3810-193 Aveiro, Portugal.
[structure: see text] Two types of covalently NH-linked porphyrin-phthalocyanine dyads, connected either through the meso phenyl group or the beta-pyrrolic position of the porphyrin, have been synthesized following statistical condensation methodologies for phthalocyanine preparation and palladium-catalyzed amination methods. Photophysical studies have revealed that energy transfer from the porphyrin to the phthalocyanine prevails regardless of linkage.
View Article and Find Full Text PDFA tightly coupled linear array of perylene, bis(porphyrin), and phthalocyanine units that functions as a photoinduced energy-transfer cascade.
J Org Chem
October 2000
Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
We have prepared a linear array of chromophores consisting of a perylene input unit, a bis(free base porphyrin) transmission unit, and a free base phthalocyanine output unit for studies in artificial photosynthesis and molecular photonics. The synthesis involved four stages: (1) a rational synthesis of trans-AB2C-porphyrin building blocks each bearing one meso-unsubstituted position, (2) oxidative, meso,meso coupling of the zinc porphyrin monomers to afford a bis(zinc porphyrin) bearing one phthalonitrile group and one iodophenyl group, (3) preparation of a bis(porphyrin)-phthalocyanine array via a mixed cyclization involving the bis(free base porphyrin) and 4-tert-butylphthalonitrile, and (4) Pd-mediated coupling of an ethynylperylene to afford a perylene-bis(porphyrin)-phthalocyanine linear array. The perylene-bis(porphyrin)-phthalocyanine array absorbs strongly across the visible spectrum.
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