ChemInform Abstract: Synthesis and Properties of Anthraquinone‐Substituted Porphyrin Compounds.

Abstract

Synthesis and Properties of Anthraquinone-Substituted PorphyrinCompounds.-Two new porphyrins [cf. (V)] are prepared. Their photochemical properties are discussed based on UV/VIS and fluorescence spectra as well as cyclic voltammetric results. -(ZHANG, J.; YANG, G.-Y.; WEN, K.; SUN, H.-R.; YU, L.-X.; CAO, X.

Synthesis of Porphyrin‐Anthraquinone Conjugates as Photosensitizing Agents

“…1). This suggests that the AQ moiety directly linked to the p porphyrin system, as in the case of compounds 12 and 13, behaves as acceptor subunit for a photoinduced electron-transfer process, [13] although it is known that the tetrapyrrolic and the emodin planes shape a wide dihedral angle, whereby complete conjugation between the p systems of the two units is precluded. [19] …”

“…The first report dates back to 1997, concerning the synthesis and photoinduced electron transfer of mono-or di-anthraquinone meso-substituted 5,15-diarylporphyrins, starting from b-alkylsubstituted dipyrrolylmethane. [13] A second and more recent article deals with an elegant synthesis of porphyrin-quinone architectures starting from the 3-cyclobutenyl-1,2-dione-substituted porphyrin that, in the presence of lithium aryl derivatives, generates naphthoquinonyl or phenantroquinonyl units directly linked to the porphyrin frame. [19] Conversely, in compounds 14 and 15, the emodin unit is linked to the para or meta position of one of the phenyl rings leaning out from the tetraphenylporphyrin structure.…”

“…A literature report describes the synthesis of AQ-substituted porphyrins, which have been studied as models for the light-initiated charge separation step in photosynthesis or as photoinduced electron-transfer devices. [13] Here we describe the previously unreported synthesis of four different porphyrin-emodin conjugates, in which the emodin moiety has been linked to a meso-phenyl of the porphyrin through ether or amido bonds or, alternatively, directly attached to one meso position of the tetrapyrrole macrocycle. Preliminary in vitro evaluation of the phototoxicity of the novel compounds was performed by means of the 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide (MTT) test on the human colon adenocarcinoma cell line HCT116, following treatment with a range of photosensitizer concentrations and irradiation with a 500-W white tungsten-halogen lamp.…”