meso-Tetraphenylporphyrin with a pi-system extended by fusion with anthraquinone

Filatov, Mikhail A.; Heinrich, Ernesta; Landfester, Katharina; Baluschev, Stanislav

doi:10.1039/c5ob00884k

Cited by 16 publications

(8 citation statements)

References 49 publications

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“…However, further theoretical work might also enlighten the special structural basis for the unusual properties of the β,β′‐naphthoquinone‐modified porphyrins. Indeed, homologation from tetra‐naphthoquinones (e.g., 6–Zn and 6‐2H ) to the corresponding tetra‐anthraquinones does not increase the special conjugative effect of the respective quinone‐type π‐extensions . Conversely, the typical covalent attachment of non‐conjugated quinone units might induce rapid quenching of the porphyrin‐centred electronically excited state, but—not unexpectedly—it barely influences the chromophore type .…”

Section: Resultsmentioning

confidence: 99%

“…Indeed, homologation from tetra-naphthoquinones (e.g., 6-Zn and 6-2H)t ot he corresponding tetra-anthraquinones does not increasethe special conjugative effect of the respective quinone-type p-extensions. [30] Conversely,t he typical covalenta ttachment of nonconjugated quinone units might inducer apid quenching of the porphyrin-centred electronicallye xcited state, but-not unexpectedly-it barely influences the chromophore type. [31] Thus, thanks to their specialp anchromatic characteristics, conjugatedt etra-b,b'-naphthoquinonoporphyrinsa re indeed exceptional molecular pigmentst hat might be particularly suitable for dye-sensitised solar-energy-converting devices.…”

Section: Crystal Structures Of Ni-porphyrinsmentioning

confidence: 99%

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Panchromatic π‐Extended Porphyrins from Conjugation with Quinones

2016

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Typical porphyrins are coloured compounds due to their characteristic wavelength‐selective visible light absorptions. An exceptional “blackened” ZnII–porphyrin was recently obtained from fusing the β,β′‐positions of the porphyrin core with four quinone units. Here, studies with metal‐free and NiII‐containing analogues are reported. These quinone‐fused porphyrins were prepared from the corresponding β,β′‐tetrasulfolenoporphyrins via thermally generated porphyrindienes, which were trapped by [4+2] cycloaddition as benzoquinone cycloadducts, which were subsequently oxidised. By using this strategy, metal‐free and NiII‐containing porphyrins with one, two, three or four conjugated naphthoquinone moieties were prepared efficiently. The presence of the π‐conjugated naphthoquinone moieties changed the porphyrin chromophores profoundly, giving broadly absorbing “blackened” pigments. The influence of coordinated NiII ions, or of the absence of a metal ion in the modified porphyrin core, on their structural and spectroscopic properties was explored. Blackened quinone‐conjugated porphyrins might be pigments suitable for solar energy conversion. With their unique peripheral functional groups they are also a set of porphyrins “programmed” for further covalent extension. Thus, they are building blocks for the preparation of supra‐porphyrinoid assemblies that might be useful in optoelectronics and in the nanosciences.

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Section: Resultsmentioning

confidence: 99%

Section: Crystal Structures Of Ni-porphyrinsmentioning

confidence: 99%

Panchromatic π‐Extended Porphyrins from Conjugation with Quinones

2016

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“…The exo-conjugation effect on the absorption properties, 36 especially the effect of fusing quinones, is subject to further investigation. 37 …”

Section: Resultsmentioning

confidence: 99%

Quinone-fused porphyrins as contrast agents for photoacoustic imaging

et al. 2017

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“…In the papers [29][30][31] the reaction of isocyanides with activated alkenes was used in the synthesis of disubstituted porphyrins in order to study their photophysical properties.…”

Section: Scheme 2 Cycloadddition Of Isocyanoacetate With Olefin Catamentioning

confidence: 99%