Difunctionalized N-Confused Porphyrins: Synthesis, Fluorescence, and Electrochemical Studies
AUSTRALIAN JOURNAL OF CHEMISTRY（2015）
摘要
Seven di-substituted N-confused porphyrins (NCPs) 9-15 bearing two aryl functional groups (cis-A(2)B(2) type) were synthesized in 4-7% yields via [3+1] approach. The corresponding five 5,10-diaryl-substituted symmetrical tripyrranes 1-5 were prepared and condensed with 2,4-bis(hydroxypentaflurophenyl)pyrrole 6. Two outer N-methyl type A(2)B(2) NCPs 14 and 15 were also prepared via a similar approach using a new key precursor 8. All the porphyrins 9-15 were characterized by high-resolution mass spectrometry, NMR, infrared spectroscopy, UV-visible spectroscopy, fluorescence spectroscopy, and cyclic voltammetry. Fluorescence studies of 9-15 showed blue-shifted emission maxima and lower Stokes shifts values when compared with N-confused tetraphenylporphyrin (NCTPP). Electrochemical studies indicated easier oxidation of N-methyl NCPs 14 and 15 when compared with remaining NCPs 9-13.
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colloids,organic chemistry,reaction mechanisms,catalysis,computational chemistry,biocatalysis,inorganic chemistry,polymer chemistry,self assembly,proteins,analytical chemistry,crystallography,interfaces,pharmaceutical chemistry,physical chemistry,educational,enzymes,kinetics,peptide,photochemistry,green chemistry,quantum chemistry,combinatorial,density functional theory,medicinal chemistry,ab initio calculations,spectroscopy,biological chemistry,macromolecules,surface chemistry,sensors,nanotechnology,structure,biosensors,electrochemistry,crystal structures,combinatorial chemistry,supramolecular chemistry,mass spectrometry,amino acids,ionic liquids
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