An electron-deficient porphyrin tape

Article abstract of DOI:10.1002/asia.201200247

Hexakis(pentafluorophenyl)-substituted meso-meso-linked Zn ^II-diporphyrin (9), which was prepared by the acid-catalyzed cross-condensation of 1,1,2,2-tetrapyrroethane (5) with dipyrromethane dicarbinol (6), was converted into meso-meso,β-β,β-β triply linked Zn^II-diporphyrin 3 by oxidation with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) and Sc(OTf)₃. Beside the red-shifted absorption spectrum and split first oxidation potential that are common to the triply-linked Zn^II-diporphyrins, diporphyrin 3 exhibited considerably improved chemical stability owing to a lowered HOMO and good solubility in common organic solvents. The two-photon absorption (TPA) cross-section and S₁-state lifetime of compound 3 were 1700 GM and 3.3 ps, respectively.