94815-62-0Relevant articles and documents
Triaryl-substituted pyrrolo-p-phenylene-linked porphyrin-fullerene dyads: Expanding the structural diversity of photoactive materials
Strelnikov, Artem A.,Androsov, Dmitriy V.,Konev, Alexander S.,Lukyanov, Daniil A.,Khlebnikov, Alexander F.,Povolotskiy, Alexey V.,Yamanouchi, Kaoru
, p. 3007 - 3019 (2018)
A protocol for the synthesis of pyrrolo-p-phenylene-linked porphyrin-fullerene dyads suitable as photoactive materials was developed. The sequence of aziridination – aziridine ring opening – 1,3-dipolar cycloaddition reactions enabled us to provide structural variability both to the porphyrin core and to pyrrole linker, which facilitates designing the electronic structure and morphological parameters of the dyads. The key porphyrin building blocks, nitro-porphyrins, were synthesized by a stochastic cyclocondensation of arenecarbaldehydes with p-nitrophenyl(dipyrrolyl)methane.
Intramolecular electron transfer of diporphyrins comprised of electron- deficient porphyrin and electron-rich porphyrin with photocontrolled isomerization
Tsuchiya, Shinji
, p. 48 - 53 (1999)
New azobenzene-linked diporphyrin Zn complexes and free base analogues were synthesized in an attempt to develop new materials for molecular electronics. These diporphyrin Zn complexes and the corresponding diporphyrins consist of electron-deficient porphyrin Zn complex and electron- rich porphyrin Zn complex or electron-deficient porphyrin and electron-rich porphyrin. These compounds, which are a new family of diporphyrins, exhibited the photoresponsive property with a structual change in the antenna; the trans-cis photoisomerization and cis-trans thermal recovery occurred and this process was reversible. A particularly noteworthy characteristic of the diporphyrin Zn complex is that its fluorescence spectrum changes with isomerization; the fluorescence intensity of the cis-isomer produced by photoirradiation is smaller than that of the trans-isomer. This fluorescence quenching of the cis-isomer arises from the intramolecular electron transfer from electron-rich porphyrin Zn complex to electron-deficient porphyrin Zn complex. Similar phenomena were observed for azobenzene-linked diporphyrins. This discovery that intramolecular electron transfer between the porphyrin rings is caused by photocontrolled isomerization is worthy of notice. Additionally, these compounds bearing eight fluorine atoms at the β-position of one porphyrin ring are the ideal materials for the practical application, because of their robust properties. This finding clearly suggests that new molecules are particularly useful in the development of photocontrolled molecular electronics such as molecular switches.
Nitroglycosylated meso-arylporphyrins as photoinhibitors of gram positive bacteria
Sol,Branland,Granet,Kaldapa,Verneuil,Krausz
, p. 3007 - 3010 (1998)
Novel porphyrins bearing nitro groups and glucosyl moieties were synthesized. The antibacterial activity of these compounds on Escherichia coli and Staphylococcus aureus is described. Results reveal that their photocytotoxicity is markedly dependent on th
Synthesis of triazole-bridged unsymmetrical porphyrin dyads and porphyrin-ferrocene conjugates
Shetti, Vijayendra S.,Ravikanth, Mangalampalli
experimental part, p. 494 - 508 (2010/04/24)
A simple method has been used to synthesize four porphyrin azides with cores such as N4, N3S, N2SO and N 2S2 in 6090% yields by treating the corresponding aminoporphyrms with tert-butyl nitrite (tBuON
Synthesis, Spectroscopy, and Photocytotoxicity of Glycosylated Amino Acid Porphyrin Derivatives as Promising Molecules for Cancer Phototherapy
Sol,Blais,Carre,Granet,Guilloton,Spiro,Krausz
, p. 4431 - 4444 (2007/10/03)
To obtain molecules that can target malignant cells, two series of new meso glucosylporphyrins bearing amino acid residues are synthesized in four steps. The first series contained n meso glycosyl moieties and (4 -n) alanyl groups on the ortho or para positions of the meso phenyl. In the second series, the carbohydrate moiety is separated from the aryl substituent by a serine unit. Starting from p- or o-nitrobenzaldehyde, p- or o-acetylbenzaldehyde or -tolualdehyde, and pyrrole, the glycosylnitrophenylporphyrins 3-6 and tritolylporphyrins 8a,b are synthesized under optimized conditions tailored from Lindsey's method. The nitro function is then reduced and N-Fmoc-L-alanine or acetylglycosylated N-Fmoc-serine are coupled on the amino function. A detailed 1H and 13C NMR study allows complete structural elucidation. The UV-visible fluorescence and MALDI mass spectra are presented. Compounds 19-22 produced 1O2, and photocytotoxicities against the K562 leukemia cell line are compared to hematoporphyrin. As a result of their sensitizing abilities, these resultant compounds are of considerable interest for photodynamic therapy.
