Tuesday, 15 May 2018
Ballroom 6ABC (Washington State Convention Center)
Among the different approaches for β-functionlization of poprhyrins, a limited number of β-arylamino functionalized poprhyirns were reported.1 Porhyrins and metallopoprhyrins that consist arylamino group have exhibited unique physiochemical and electrochemical redox properties and utilized for various applications such as dye-sensitized solar cells (DSSCs), catalysis, and nonlinear optics.2 In this regard, we report the regioselective synthesis of 2-arylamino-12,13-dibromo-5,10,15,20-tetraphenylporphyrins and their metal (Cu(II) and Zn(II)) complexes (Fig. 1a). The palladium catalyzed coupling reaction of tetrabromoporphyrin with substituted anilines yielded various mono-β-arylamino substituted poprhyrins. All β-arylamino porphyrins were characterized by UV-Vis, fluorescence, 1H NMR spectroscopic techniques and cyclic voltammetry studies. β-arylamino porphyrins exhibited broadened absorption spectra which consist one Soret and two Q bands as shown in Fig. 1b. Notably, β-arylamino porphyrins exhibited multiple oxidations and reductions due to 'push-pull' β-substituents which alters the energy levels of frontier molecular orbitals. DFT studies revealed that these porphyrins are having quasiplanar confirmation. In this presentation, we will discuss about the regioselective synthesis, spectral, electrochemical redox properties of β-arylamino functionalized porphyrins in detail.