Cyclisation involving a meso-phenyl substituent of a metalloporphyrin: X-ray structure of 5,10,15-triphenyl{22-oxo-benzo[2324]cyclohexa[a,b]porphinato(2-)}copper(II)

Henrick, Kim; Owston, P. G.; Peters, R.; Tasker, Peter A.; Dell, A.

doi:10.1016/s0020-1693(00)80132-2

Cited by 35 publications

(18 citation statements)

References 9 publications

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“…in 2005. In the reaction of the well‐known keto‐napthoporphyrin 12 with hydrazine hydrate in CH 2 Cl 2 −MeOH, in situ generation of diimide occurred, which in turn reacted with the β,β’‐double bond opposite to the ring fusion unit and produced chlorin 68 (Scheme ) . This reaction occurred as a consequence of reduction of the most reactive cross‐conjugated opposite β,β’‐double bond.…”

Section: Classification Of Ring‐annulated Chlorinsmentioning

confidence: 99%

β‐meso‐Annulated meso‐Tetraarylchlorins: A Study of the Effect of Ring Fusion on Chlorin Conformation and Optical Spectra

Banerjee

Phadte

2020

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Chlorins are a class of reduced porphyrins with a very intense longest wavelength Q band (Q y) in the red region, due to their non-planar conformations. This fact is useful in fields like photodynamic therapy and organic photovoltaics, which rely upon the long wavelength absorptivity of the photosensitizing dyes. Here, we have reviewed the synthesis and optical properties of many novel β-meso-annulated chlorins, which possess bathochromic shifts in their optical spectra, compared to their non-fused analogues. In general, we find that these red-shifts are promoted by planarization of the macrocycle caused by β-meso-ring fusion. However, in select examples of ring-fused chlorins bearing an additional non-pyrrolic subunit, in fact we see strong deviation from planar conformation contrary to the general trend. These molecules show Q y bands in the NIR region, but with reduced absorptivity.

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Section: Classification Of Ring‐annulated Chlorinsmentioning

confidence: 99%

β‐meso‐Annulated meso‐Tetraarylchlorins: A Study of the Effect of Ring Fusion on Chlorin Conformation and Optical Spectra

Banerjee

Phadte

2020

ChemistrySelect

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“…The initial reaction, actually found by accident on attempting to demetallate copper 2-formylTPP 12 (M = Cu) in an acidic medium, involved an aldehyde and resulted in the isolation of ketone 13 (M = Cu) in very low yield [11]. Reinvestigation of the reaction using 12 (M = Ni) showed that 13 could be isolated in high yield in addition to 14 and additional reduced products (Scheme 4), all resulting from the dismutation of an initial allylic alcohol [8,12].…”

Section: Acid-catalyzed Cyclization Of 2-formylporphyrinsmentioning

confidence: 99%

Meso-aryl-ß-pyrrolic positions interactions in meso-tetraarylporphyrins: Flat arylporphyrins and building blocks for oligoporphyrins

Callot

Ruppert

Jeandon

et al. 2004

J. Porphyrins Phthalocyanines

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Aryl groups bound to the meso positions of porphyrins often react with neighboring groups, in particular ß-acyl groups to give highly diversified monomeric and dimeric new functionalized porphyrins. The products, whose meso-aryl ring approaches coplanarity with the porphyrin macrocycle, show large shifts of UV-visible absorption bands and various potentialities for building external chelating moieties and assembling oligoporphyrins.

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“…Introducing bridges linking the phenyl group to one of the neighboring β-positions of a pyrrole ring forces the phenyl ring into a conformation, which is nearly aligned with the porphyrin plane. 8 Constructing discotic columnar mesophases from meso-bridged porphyrins has the potential to create useful elements for directed, one dimensional electron transfer processes.…”

Section: Introductionmentioning

confidence: 99%

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A series of meso-β bridged extended porphyrins substituted with long aliphatic chains were synthesized and fully characterized. Two different synthetic strategies were tested to obtain the target structures. The synthetic steps were optimized in order to obtain scalable routes for the production of sufficient quantities of π-extended porphyrins for material science studies. The porphyrins were obtained either as free bases or complexed with Ni II or Cu II . UV-Vis spectroscopy and polarized light microscopy was used for the analysis of the material properties of the π-extended porphyrins. The results obtained with our compounds are not compatible with the results reported in the literature.

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Cyclisation involving a meso-phenyl substituent of a metalloporphyrin: X-ray structure of 5,10,15-triphenyl{22-oxo-benzo[2324]cyclohexa[a,b]porphinato(2-)}copper(II)

Cited by 35 publications

References 9 publications

β‐meso‐Annulated meso‐Tetraarylchlorins: A Study of the Effect of Ring Fusion on Chlorin Conformation and Optical Spectra

β‐meso‐Annulated meso‐Tetraarylchlorins: A Study of the Effect of Ring Fusion on Chlorin Conformation and Optical Spectra

Meso-aryl-ß-pyrrolic positions interactions in meso-tetraarylporphyrins: Flat arylporphyrins and building blocks for oligoporphyrins

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