Funktionalisierte <i>meso</i>‐Arylporphyrine als Edukte für die Synthese von Oligoporphyrinylen

Hammel, Dirk; Kautz, Christian; Müllen, Kläus

doi:10.1002/cber.19901230625

Cited by 15 publications

(9 citation statements)

References 10 publications

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“…Bisporphyrins linked by stilbene groups have been previously reported by Mullen and co-workers . In addition Ono et al have prepared a series of bisporphyrins where the number of stilbene linkers was varied between one and four.…”

Section: Resultsmentioning

confidence: 96%

Stepwise Syntheses of Bisporphyrins, Bischlorins, and Biscorroles, and of Porphyrin−Chlorin and Porphyrin−Corrole Heterodimers

et al. 1996

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The stepwise syntheses and characterization of a series of symmetrical and unsymmetrical bisporphyrins, bischlorins, and biscorroles, and of porphyrin−chlorin and porphyrin−corrole dyads possessing ethylene, phenyl, and stilbene linking units are described. The methodology for synthesis of 10-substituted corroles 2 and their cobalt complexes 9 via a,c-biladiene salts 1 was first developed, and then extended to provide biscorroles (e.g., 4 and 5) linked through the 10-positions with phenyl linker units. Using a similar methodology, phenyl-linked corrole−porphyrin dyads 28 and 30 were also prepared. By way of intermediate phenyl-linked unsymmetrical bisdipyrromethanes, a completely unsymmetrical heterobimetallic bisporphyrin system, 45, was synthesized. Low-valent titanium coupling (McMurry) reactions were used to prepared stilbene-linked bisdipyrromethanes (e.g., 46) which were subsequently transformed into stilbene-linked bisporphyrins (e.g., 48). McMurry cross-coupling reactions of porphyrins bearing p-formylphenyl substituents also afforded an unsymmetrically substituted bisporphyrinylstilbene, 60, as well as the corresponding homodimers 56 and 59. Likewise, McMurry cross-coupling of a p-formylphenyl-substituted porphyrin, 62, with a formylchlorin, 63, afforded a stilbene-linked bisporphyrin, 64, a bischlorin, 66, and a novel porphyrin−chlorin heterodimer, 65. All novel products were characterized by 1H NMR, UV−vis, and mass spectroscopy and elemental analysis. X-ray structural information was also obtained for the zinc/nickel bisporphyrin 45 and for the bis-nickel porphyrin−chlorin 65.

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Section: Resultsmentioning

confidence: 96%

Stepwise Syntheses of Bisporphyrins, Bischlorins, and Biscorroles, and of Porphyrin−Chlorin and Porphyrin−Corrole Heterodimers

et al. 1996

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“…The aminopropylsilylated ITO electrode was then immersed in a 1 mmol L −1 toluene solution of C 60 for two days under reflux to give C 60 ‐ref /ITO 26. Porphyrin aldehydes 1 – 3 28b, 29, 30 were coupled to C 60 ‐ref /ITO by refluxing in the presence of N ‐methylglycine for three days in toluene to give Fc‐P‐CONH‐C 60 /ITO (P=ZnP or H 2 P), P‐CONH‐C 60 /ITO (P=ZnP or H 2 P), and P‐S1‐C 60 /ITO (P=ZnP or H 2 P), respectively 31. The 1,3‐dipolar cycloaddition of azomethine ylides to C 60 affording fulleropyrolidines occurs exclusively across [6,6] bonds 31.…”

Section: Resultsmentioning

confidence: 99%

Vectorial Electron Relay at ITO Electrodes Modified with Self‐Assembled Monolayers of Ferrocene–Porphyrin–Fullerene Triads and Porphyrin–Fullerene Dyads for Molecular Photovoltaic Devices

Imahori

Kimura

Hosomizu

et al. 2004

Chemistry A European J

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Systematic series of indium tin oxide (ITO) electrodes modified covalently with self-assembled monolayers (SAMs) of ferrocene-porphyrin-fullerene triads and porphyrin-fullerene dyads were designed to gain valuable insight into the development of molecular photovoltaic devices. The structures of SAMs on ITO have been investigated by UV/Vis absorption spectroscopy, atomic force microscopy, and cyclic voltammetry. The photoelectrochemical and photophysical (fluorescence lifetime and time-resolved transient absorption) properties were also determined. The highest quantum yield of photocurrent generation (11 %) among donor-acceptor linked systems which are covalently attached to the surface of ITO electrodes was achieved with SAMs of ferrocene-zinc porphyrin-fullerene linked triad on ITO electrodes. The quantum yields of photocurrent generation correlate well with the charge-separation efficiency and the lifetime of the charge-separated state of the porphyrin-fullerene linked systems in solution. These results provide valuable information for the construction of photonic molecular devices and artificial photosynthetic systems on ITO electrodes.

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“…4-Dimethylaminobenzaldehyde 2a and ferrocene carboxaldehyde 2b were purchased from CarloErba and Aldrich respectively, and used as received. Formyl-substituted porphyrin 2c 44 and N-Boc-protected aminoacid 1 45 were prepared according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

Redox-active Si(100) surfaces covalently functionalised with [60]fullerene conjugates: new hybrid materials for molecular-based devices

et al. 2008

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Herein, we report the covalent immobilisation, through Si-C bonds, of various [60]fullerene derivatives on flat silicon surfaces following three different preparative protocols. Each synthetic strategy comprises a two-step approach that includes a pre-modification step of the Si(100) surface with an organic monolayer bearing a terminal functionality that undergoes a bond-forming reaction with a [60]fullerene synthon as characterized by X-ray photoelectron spectroscopy (XPS) measurements. Water contact angle measurements clearly showed a characteristic change of the surface hydrophobicity upon covalent immobilisation of the carbon functions. The hybrid [4b-Si(100)] surfaces, containing [60]fullerene-ferrocene fragments, were also investigated by means of cyclic voltammetry (CV), and were revealed to be exceptionally robust towards repeated reduction-oxidation cycles. Moreover, several surface-confined redox couples were observed in CH(3)CN solution. The surface coverage was measured to be ca. 2.5 x 10(-11) mol cm(-2)

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Funktionalisierte meso‐Arylporphyrine als Edukte für die Synthese von Oligoporphyrinylen

Cited by 15 publications

References 10 publications

Stepwise Syntheses of Bisporphyrins, Bischlorins, and Biscorroles, and of Porphyrin−Chlorin and Porphyrin−Corrole Heterodimers

Stepwise Syntheses of Bisporphyrins, Bischlorins, and Biscorroles, and of Porphyrin−Chlorin and Porphyrin−Corrole Heterodimers

Vectorial Electron Relay at ITO Electrodes Modified with Self‐Assembled Monolayers of Ferrocene–Porphyrin–Fullerene Triads and Porphyrin–Fullerene Dyads for Molecular Photovoltaic Devices

Redox-active Si(100) surfaces covalently functionalised with [60]fullerene conjugates: new hybrid materials for molecular-based devices

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