847375-27-3Relevant articles and documents
Bioinspired nanophotosensitizers: Synthesis and characterization of porphyrin-noble metal nanoparticle conjugates
Bhaumik, Jayeeta,Gogia, Gitanjali,Kirar, Seema,Vijay, Lekshmi,Thakur, Neeraj S.,Banerjee, Uttam C.,Laha, Joydev K.
, p. 724 - 731 (2016/01/12)
A methodology to enhance biological delivery of photosensitizers by incorporating them into nanomaterials has been developed. In order to prepare photosensitizer nanoconjugates as biocompatible and selective probes, initially, bioconjugatable porphyrinic
Masked imidazolyl-dipyrromethanes in the synthesis of imidazole-substituted porphyrins
Bhaumik, Jayeeta,Yao, Zhen,Borbas, K. Eszter,Taniguchi, Masahiko,Lindsey, Jonathan S.
, p. 8807 - 8817 (2007/10/03)
Imidazole-substituted metalloporphyrins are valuable for studies of self-assembly and for applications where water solubility is required. Rational syntheses of porphyrins bearing one or two imidazol-2-yl or imidazol-4-yl groups at the meso positions have been developed. The syntheses employ dipyrromethanes, 1-acyldipyrromethanes, and 1,9-diacyldipyrromethanes bearing an imidazole group at the 5-position. The polar, reactive imidazole unit was successfully masked by use of (1) the 2-(trimethylsilyl)ethoxymethyl (SEM) group at the imidazole pyrrolic nitrogen, and (2) a dialkylboron motif bound to the pyrrole of the dipyrromethane and coordinated to the imidazole imino nitrogen. The nonpolar nature of such doubly masked imidazolyl-dipyrromethanes facilitated handling. Selected masked dipyrromethanes were characterized by 11B and 15N NMR spectroscopy. Five distinct methods were examined to obtain trans-A2B2-, trans-AB2C-, and trans-AB-porphyrins. Each porphyrin contained one or two SEM-protected imidazole units. The SEM group could be removed with TBAF or HCl. Two zinc(II) porphyrins and a palladium(II) porphyrin bearing a single imidazole moiety were prepared and subjected to alkylation (with ethyl iodide, 1,3-propane sultone, or 1,4-butane sultone) to give water-soluble imidazolium-porphyrins. This work establishes the foundation for the rational synthesis of a variety of porphyrins containing imidazole units.