950669-10-0Relevant academic research and scientific papers
A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole
Filatov, Mikhail A.,Cheprakov, Andrei V.,Beletskaya, Irina P.
, p. 3468 - 3475 (2007)
A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of the aromatization of annelated rings, which is the most serious bottleneck in previo
Synthesis of phosphorescent asymmetrically π-extended porphyrins for two-photon applications
Esipova, Tatiana V.,Vinogradov, Sergei A.
, p. 8812 - 8825 (2015/02/19)
Significant effort has been directed in recent years toward porphyrins with enhanced two-photon absorption (2PA). However, the properties of their triplet states, which are central to many applications, have rarely been examined in parallel. Here we repor
Synthesis of 5,15-diaryltetrabenzoporphyrins
Filatov, Mikhail A.,Lebedev, Artem Y.,Vinogradov, Sergei A.,Cheprakov, Andrei V.
, p. 4175 - 4185 (2008/09/20)
(Chemical Equation Presented) A general method of synthesis of 5,15-diaryltetrabenzoporphyrins (Ar2TBPs) has been developed, based on 2 + 2 condensation of dipyrromethanes followed by oxidative aromatization. Two pathways to Ar2TBPs were investigated: the tetrahydroisoindole pathway and the dihydroisoindole pathway. In the tetrahydroisoindole pathway, precursor 5,15-diaryltetracyclohexenoporphyrins (5,15-Ar2TCHPs) were assembled from cyclohexeno-fused meso-unsubstituted dipyrromethanes and aromatic aldehydes or, alternatively, by way of the classical MacDonald synthesis. In the first case, scrambling was observed. Aromatization by tetracyclone was more effective than aromatization by DDQ but failed in the cases of porphyrins with electron-withdrawing substituents in the meso-aryl rings. The dihydroisoindole pathway was found to be much superior to the tetrahydroisoindole pathway, and it was developed into a general preparative method, consisting of (1) the synthesis of 4,7-dihydroisoindole and its transformation into meio-unsubstituted dipyrromethanes, (2) the synthesis of 5,15-diaryloctahydrotetrabenzoporphyrins (5,15-Ar2OHTBPs), and (3) their subsequent aromatization by DDQ. Ar2TBP free bases exhibit optical absorption spectra similar to those of meso-unsubstituted tetrabenzoporphyrins and fluoresce with high quantum yields. Pd complex of Ph2TBP was found to be highly phosphorescent at room temperature.
