Rational Synthesis of Imidazolyl Porphyrinic Molecules for Self-assembly and Water-solubility

Porphyrin;Imidazole;Self-assembly;Water-soluble

Bhaumik, Jayeeta ; T. Brent Gunnoe, Committee Member,Jonathan S. Lindsey, Committee Chair,Daniel L. Comins, Committee Member,Bhaumik, Jayeeta ; T. Brent Gunnoe ; Committee Member ; Jonathan S. Lindsey ; Committee Chair ; Daniel L. Comins ; Committee Member

University:North Carolina State University

关键词: Porphyrin;    Imidazole;    Self-assembly;    Water-soluble;   

Others  :  https://repository.lib.ncsu.edu/bitstream/handle/1840.16/2004/etd.pdf?sequence=1&isAllowed=y

美国|英语

来源: null

【 摘 要 】

The objective of this work is to develop synthetic methodology for self-assembling and water-soluble imidazole-containing porphyrinic molecules.The synthesis of the following types of compounds is described: (1) Imidazole-containing porphyrinic compounds; (2) Derivatization of the imidazolyl porphyrins to obtain water-soluble imidazolium porphyrins, and (3) Improved synthesis of tetrahydrodipyrrins - a precursor of hydroporphyrins.The self-assembly of imidazolyl metalloporphyrins was examined by UV-VIS spectroscopic analysis.Each imidazoyl metalloporphyrin was found to aggregate in non-polar solvents such as CH2Cl2.The test of water solubility was also based on absorption spectroscopy.A refined synthesis of a tetrahydrodipyrrin is described for medium-scale synthesis (>10 g of the product), which facilitates access to diverse hydroporphyrins.Water-soluble porphyrinic molecules are useful for life sciences applications, and the tetrahydrodipyrrin precursors are important for the synthesis of a variety of hydroporphyrins.Taken together, this work advances the methodology for preparing a variety of synthetic porphyrins.