Azo Dyes Based on 1,10-Phenanthroline

A series of new phenanthroline based azo-dye ligands, produced by diazotizing 5-amino-1,10-phenanthroline (5-NH2-phen) and then coupling this intermediate to a variety of coupling components, has been synthesized and characterized. The coupling components used were β-naphthol, phenol, and 2,6-dimethylphenol, and the three dye ligands were named phen-azo-β-naphthol, phen-azo-p-phenol, and phen-azo-2,6-dimethylphenol, respectively. 1H-NMR and IR spectra showed that the dyes exist primarily in the azo form in DMSO solution and as solids. UV-Vis spectra (in MeOH) showed intense (ε ≅ 104 M-1cm-1) absorptions ranging from 380 nm to 500 nm for these ligands. The ligand phen-azo-p-phenol has been coordinated to a Re(I) metal center through the phenanthroline linkage to form a stable polypyridyl complex, fac-ReI(CO)3(phen-azo-p-phenol)Cl. When compared to the well-known complex fac-ReI(CO)3 (phen)Cl, the new Re(I)-dye complex shows a greatly enhanced visible absorption band in the 370 - 400 nm range. This absorption is primarily due to a ligand-centered transition in the coordinated phen-dye ligand. Preliminary emission spectra (in MeOH) reveal that fac-ReI(CO)3(phen-azo-p-phenol)Cl, unlike its Re(I)-phen analog, does not emit

Azo Dyes Based on 1,10-Phenanthroline

A series of new phenanthroline based azo-dye ligands, produced by diazotizing 5-amino-1,10-phenanthroline (5-NH2-phen) and then coupling this intermediate to a variety of coupling components, has been synthesized and characterized. The coupling components used were β-naphthol, phenol, and 2,6-dimethylphenol, and the three dye ligands were named phen-azo-β-naphthol, phen-azo-p-phenol, and phen-azo-2,6-dimethylphenol, respectively. 1H-NMR and IR spectra showed that the dyes exist primarily in the azo form in DMSO solution and as solids. UV-Vis spectra (in MeOH) showed intense (ε ≅ 104 M-1cm-1) absorptions ranging from 380 nm to 500 nm for these ligands. The ligand phen-azo-p-phenol has been coordinated to a Re(I) metal center through the phenanthroline linkage to form a stable polypyridyl complex, fac-ReI(CO)3(phen-azo-p-phenol)Cl. When compared to the well-known complex fac-ReI(CO)3 (phen)Cl, the new Re(I)-dye complex shows a greatly enhanced visible absorption band in the 370 - 400 nm range. This absorption is primarily due to a ligand-centered transition in the coordinated phen-dye ligand. Preliminary emission spectra (in MeOH) reveal that fac-ReI(CO)3(phen-azo-p-phenol)Cl, unlike its Re(I)-phen analog, does not emit

6-[(4-Hy­droxy­phen­yl)diazenyl]-1,10-phenanthrolin-1-ium chloride monohydrate

In the cation of the title mol­ecular salt, C18H13N4O+·Cl−·H2O, the dihedral angle between the mean planes of the 1,10-phenanthroline system and the phenol ring is 14.40 (19)°. The crystal packing is stabilized by O—H⋯O hydrogen bonds, weak N—H⋯Cl and O—H⋯Cl inter­molecular inter­actions and π—π stacking inter­actions [centroid–centroid distance = 3.6944 (13) and 3.9702 (12) Å