Novel Synthetic Cycloketo‐Tetraphenylporphyrins

Abstract

New tetraphenylporphyrins 2a and 2b have been synthesized and characterized. Both compounds possess an ethanone bridge that connects the porphyrin ring with one of the phenyl groups at the periphery. Tetraphenylporphyrin 2a also has a methyl group on the same phenyl ring, whereas tetraphenylporphyrin 2b lacks this substituent. This small difference results in 2a and 2b having markedly different photophysical properties. In particular, 2a proved to be a highly efficient sensitizer for singlet oxygen generation with a quantum yield of 0.85. A reference compound 2c has also been synthesized in which the porphyrin ring is connected to one of the peripheral phenyl groups through just a keto function. Thus, the effect of the size of the exocyclic ring on conjugation and photophysical properties has been studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Aggregation of asphaltene model compounds using a porphyrin tethered to a carboxylic acid

“…The desired target, porphyrin 7a, was then reacted with HBr in 75 AcOH, according to a procedure by Jux, 52 to give bromide 7b, which was used without further purification. The route of Jasinski et al for cyanation of bromomethyl TPPs was modified slightly, 54 and treatment of the crude bromide 7b with KCN in PEG 400 gave the cyanomethyl substituted porphyrin 9 in excellent yield. 80 Hydrolysis of the nitrile 9 under acidic conditions yielded the carboxylic acid, and the free base porphyrin 10 was isolated in good yield via column chromatography.…”

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…The most significant shift was observed on the two lowest-energy bands in the case of trimer 223.8 (690 nm vs 789 nm, and 758 nm vs 881 nm, in 223.5 and 223.8 , respectively). An extension of the above cyclization approach, producing 7-membered rings, was reported by Jux, Röder, et al…”

Photodynamic effects induced by meso-tris(pentafluorophenyl)corrole and its cyclodextrin conjugates on cytoskeletal components of HeLa cells

“…The setup for detection of the luminescence signal has been reported previously [27,28]. To calculate the singlet oxygen quantum yield, F D , TPP in DMF was used as reference (F D ¼ 0.65) [29]. The optical density of all samples and reference was 0.05 at the excited wavelength (616 nm).…”

“…5,10,15,20-tetraphenylporphyrin (TPP) in DMF was used as reference (F D ¼ 0.65) [29]. All corroles, and TPP were excited at 616 nm, in DMF (OD 616nm ¼ 0.05).…”