Electrochemical and Spectroscopic Characterization of Aluminium(III)-para-methyl-meso-tetraphenylporphyrin Complexes Containing Substituted Salicylates as Axial Ligands

Abstract

A series of aluminium(III)-p-methyl-meso-tetraphenylporphyrin (p-CH3TPP-Al(III)) containing axially coordinated salicylate anion [p-CH3TPP-Al-X)], where X = salicylate (SA), 4-chlorosalicylate (4-CSA), 5-chlorosalicylate (5-CSA), 5-flourosalicylate (5-FSA), 4-aminosalicylate (4-ASA), 5-aminosalicylate (5-ASA), 5-nitrosalicylate (5-NSA), and 5-sulfosalicylate (5-SSA), have been synthesized and characterized by various spectroscopic techniques including ultraviolet-visible (UV-vis), infrared (IR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy,13C NMR, and elemental analysis. A detailed study of electrochemistry of all the synthesized compounds has been done to compare their oxidation and reduction mechanisms and to explain the effect of axial coordination on their redox properties.

Tunable functionalization of graphene nanosheets for graphene-organic hybrid photodetectors

“…However, in the case of the ZnTPP-and Al(III)TPP-graphene hybrid layers, a noticeable change in the relative intensities and positions of the Q-bands was observed. Furthermore, only two Q-band absorption peaks appeared in the ZnTPP-and Al(III)TPP-graphene spectra due to the higher symmetry of the molecular species [39,40]. These results confirmed that ZnTPP and Al(III)TPP were successfully formed on the graphene surface.…”

Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

“…Recently, 2‐nitro‐5,10,15,20‐tetrakis(pentafluorophenyl)porphyrin ( 90 ) was obtained with an acceptable yield of 50%, by nitration of the proper substrate with indium nitrite In(NO 2 ) 3 , in a mixture of acetic acid anhydride and acetic acid followed by decomplexation (Scheme 31). [87] The above product was prepared for enzymatic investigations.…”

On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins

“…This reaction has been extensively studied and experimental procedures for selective mono-b-nitration were developed for a wide variety of porphyrins bearing meso-aryl substituents at the macrocycle periphery. [19][20][21][22][23][24][25][26][27][28][29] Among different synthetic procedures developed for the nitration of meso-tetraarylporphyrins, the treatment of free base porphyrins with copper(II) nitrate in the presence of acetic anhydride seems to be the most convenient and general procedure. 19 In fact, the reactivity of each porphyrin in 2H-1 series under these conditions was somewhat different but after optimization of the reagent amount, the temperature and the reaction time, all 2-nitroporphyrins Cu-4(a-f) were obtained in good to high yields (Scheme 2, 68-84%) (see ESI, † Table S1).…”

“…We have studied the preparation of these modular systems from available mesotetraarylporphyrins 2H-1 focusing our studies on the mild procedures tolerated by different functional groups (Scheme 1). In this regard, mono b-aminoporphyrins 2H-2 seem to be attractive intermediate compounds because of their ready availability from meso-tetraarylporphyrins 2H-1 by using nitration, [19][20][21][22][23][24][25][26][27][28][29][30] followed by the reduction of the nitro group. 21,[31][32][33][34][35][36] Scheme 1 briefly summarizes different synthetic approaches to modular porphyrins from 2-aminoporphyrins 2H-2.…”