Synthesis and luminescence of soluble meso-unsubstituted tetrabenzo- and tetranaphtho[2,3]porphyrins.
[Structure: see text]. Syntheses of soluble tetrabenzoporphyrins (TBP) and tetranaphtho[2,3]porphyrins (TNP), with multiple substituents in the conjugated aromatic rings but bearing no substituents in the meso-positions, is reported. Both types of porphyrins were obtained by direct aromatization of precursor porphyrins, annealed with either cyclohexene or dihydronaphthalene fragments. TBPs and TNPs possess powerful absorption bands in the near-infrared (lambda = 610-710 nm, epsilon = 100,000-300,000 M(-1) cm(-1)) and exhibit strong luminescence. Free bases and Zn complexes fluoresce with quantum yields of up to 50%, whereas Pd and Pt complexes phosphoresce in solutions at ambient temperatures. Remarkably, the phosphorescence quantum yields of Pd and Pt TBPs reach as high as 20-50%, which places them among the brightest near-infrared phosphors known to date.
Finikova
Olga S
OS
Department of Biochemistry and Biophysics, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Cheprakov
Andrei V
AV
Vinogradov
Sergei A
SA
D049449:Luminescence; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011166:Porphyrins; D012995:Solubility; D015032:Zinc / Q000737:chemistry
D008665:Metalloporphyrins; D011166:Porphyrins; D015032:Zinc