Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

Abstract

2,4,6-Trichloro-1,3,5-triazine (cyanuric chloride) is an excellent coupling reagent for the preparation of highly structured multifunctional molecules. Three component systems based on porphyrin, cyanuric chloride and carborane clusters were prepared by a one-pot stepwise amination of cyanuric chloride with 5-(4-aminophenyl)-10,15,20-triphenylporphyrin, followed by replacement of the remaining chlorine atoms with carborane S- or N-nucleophiles. Some variants of 1,3,5-triazine derivatives containing porphyrin, carborane and residues of biologically active compounds such as maleimide, glycine methyl ester as well as thioglycolic acid, mercaptoethanol and hexafluoroisopropanol were also prepared. A careful control of the reaction temperature during the substitution reactions will allow the synthesis of desired compounds in a good to high yields. The structures of synthesized compounds were determined with UV-vis, IR, 1H NMR, 11B NMR, MALDI-TOF or LC-MS spectroscopic data. The dark and photocytotoxicity as well as intracellular localization and photoinduced cell death for compounds 8, 9, 17, 18 and 24 were evaluated.

Nickel(II) and Palladium(II) Complexes with η5:κ1(N)-Coordinated Dicarbollide Ligands Containing Pendant Pyridine Group

“…To obtain a related nido-carborane with a pendant pyridyl group attached to the carbon atom, as a development of the known approach to the arylation and heteroarylation of 1-mercapto-ortho-carborane [71][72][73][74], we used the reaction of the trimethylammonium salt of 1-mercapto-ortho-carborane with 2-bromopyridine. The reaction in refluxing ethanol gave a mixture of the expected pyridyl derivative of ortho-carborane 1-(NC 5 H 4 -2 -S)-1,2-C 2 B 10 H 11 (2) and its deboronation product as the N-protonated intramolecular salt [7-(HNC 5 H 4 -2 -S)-7,8-C 2 B 9 H 11 ] (H [3]), which were separated using column chromatography on silica followed by the conversion of the latter to the cesium salt Cs[7-(NC 5 H 4 -2 -S)-7,8-C 2 B 9 H 11 ] (Cs [3]) (Scheme 2).…”

Enhanced Catalytic Activity of Binuclear Oxidovanadium(IV) Bisbenzimidazole Linked Porphyrin Dimer for the Generation of Biologically Active 3,4-Dihydropyrimidinones and Their Corresponding Thiones

“…Porphyrin and its analogues show distinctive physiological and electrochemical features due to their inherited aromatic structure. , Due to their adaptable excitation and emission spectral features, metalloporphyrins are particularly beneficial in dye-sensitized solar cells, − catalysis, − ion sensing, − nonlinear optics, , sorbents, , and photodynamic therapy. , By variation of the peripheral functionalization, one may alter the physicochemical and catalytic properties of the porphyrin macrocycle. In contrast to meso -aryl functionalization, the functionalization at β-position has stronger electronic and steric effects. , …”