Poly- and oligometalloporphyrins associated through coordination

Wojaczyński, Jacek; Latos‐Grażyński, Lechosław

doi:10.1016/s0010-8545(99)00207-6

Cited by 251 publications

(119 citation statements)

References 424 publications

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“…[21][22][23] The ability of metalloporphyrins to coordinate with axial ligands containing nitrogen, oxygen or sulfur atoms gives a great variety of self-assembled superstructures, with facility to tune their optical and electronic properties, as is the case of many zinc (II) metalloporphyrins that form stable supramolecules in non-polar media when they self-assemble through coordinating ligands. 24,25 The coordination of zinc porphyrins with axial nitrogen derivative ligands, such as imidazolyl or pyridyl groups afford the formation of well-organized macromolecules in the form of cyclic structures, [26][27][28][29] or linear polymers 30,31 and oligomers. [32][33][34] The coordination between zinc(II) and pyridyl ligands has a relatively large association constant (~10 3 M -1 ) 35,36 and usually does not disturb the photoexcited state of the metalloporphyrin.…”

Section: Introductionmentioning

confidence: 99%

Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds

et al. 2015

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A series of chiral synthetic compounds is reported that show intricate but specific hierarchical assembly because of varying positions of coordination and hydrogen bonds. The evolution of the aggregates (followed by absorption spectroscopy and temperature-dependent circular dichroism studies in solution) reveal the influence of the proportion of stereogenic centers in the side groups connected to the chromophore ring in their optical activity and the important role of pyridyl groups in the self-assembly of these chiral macrocycles. The optical activity spans two orders of magnitude depending on composition and constitution. Two of the aggregates show very high optical activity even though the isolated chromophores barely give a circular dichroism signal. Molecular modeling of the aggregates, starting from the pyridine-zinc(II) porphyrin interaction and working up, and calculation of the circular dichroism signal confirm the origin of this optical activity as the chiral supramolecular organization of the molecules. The aggregates show a broad absorption range, between approximately 390 and 475 nm for the transitions associated with the Soret region alone, that spans wavelengths far more than the isolated chromophore. The supramolecular assemblies of the metalloporphyrins in solution were deposited onto highly oriented pyrolitic graphite in order to study their hierarchy in assembly by atomic force microscopy. Zero and one-dimensional aggregates were observed, and a clear dependence on deposition temperature was shown, indicating that the hierarchical assembly took place largely in solution. Moreover, scanning electron microscopy images of porphyrins and metalloporphyrins precipitated under out-ofequilibrium conditions showed the dependence of the number and position of chiral amide groups in the formation of a fibrillar nanomaterial. The combination of coordination and hydrogen bonding in the complicated assembly of these molecules -where there is a clear hierarchy for zinc(II)-pyridyl interaction followed by hydrogen-bonding between amide groups, and then van der Waals interactions -paves the way for the preparation of molecular materials with multiple chromophore environments.

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Section: Introductionmentioning

confidence: 99%

Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds

et al. 2015

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“…In this context, metalloporphyrins are remarkable precursors in supramolecular chemistry, giving rise to various architectures and properties [1][2][3][4]. To illustrate this point, several examples can be cited as photodynamic therapy, information storage devices, photoelectrical devices as photocells and light-emitting diodes (that transform energy in both directions), and receptors (exploiting their ability to selectively form complexes which can sharply change the spectral properties) [5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Self-assembly of iron TCPP (meso-tetra(4-carboxyphenyl)porphyrin) into a chiral 2D coordination polymer

et al. 2011

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“…9 The vast majority of self-complexed metalloporphyrin oligomers involve zinc porphyrins, which have a shorter singlet state excited lifetime than their Mg(II) analogues but are synthetically more accessible. 1a,2,3, 10 Until the mid 1990's magnesium(II) porphyrins have been avoided by synthetic chemists due to the problems associated with the insertion of Mg(II) into the inner core of porphyrinic macrocycles. This obstacle has been removed by the heterogeneous and homogeneous Mg(II) insertion methods of Lindsey and co-workers.…”

Section: Introductionmentioning

confidence: 99%

Multiporphyrin coordination arrays based on complexation of magnesium(ii) porphyrins with porphyrinylphosphine oxides

2007

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Di-and triporphyrin arrays consisting of 5,15-diphenylporphyrinatomagnesium(II) (MgDPP) coordinated to free-base and Ni(II) porphyrinyl mono-and bis-phosphine oxides, as well as the self-coordinating diphenyl [10,20- demonstrate the strong affinity of phosphine oxides towards Mg(II) porphyrins. These complexes are the first strongly bound synthetic Mg(II) multiporphyrin complexes and could potentially mimic the "special pair" in the photosynthetic reaction centre.

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Poly- and oligometalloporphyrins associated through coordination

Cited by 251 publications

References 424 publications

Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds

Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds

Self-assembly of iron TCPP (meso-tetra(4-carboxyphenyl)porphyrin) into a chiral 2D coordination polymer

Multiporphyrin coordination arrays based on complexation of magnesium(ii) porphyrins with porphyrinylphosphine oxides

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