Electropolymerizable peripherally tetra-{2-[3-(diethylamino)phenoxy]ethoxy} substituted as well as axially (4-phenylpiperazin-1-yl)propanoxy-disubstituted silicon phthalocyanines and their electrochemistry

Abstract

A novel type of peripherally tetra-substituted as well as axially disubstituted silicon(iv) phthalocyanine containing electropolymerizable ligands was designed and synthesized for the first time. Axial bis-hydroxy silicon phthalocyanine 2 was prepared from 2(3),9(10),16(17),23(24)-tetrakis-{2-[3-(diethylamino)phenoxy]ethoxy}phthalocyanine 1 in dichloromethane by using 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU) and trichlorosilane. Peripherally tetra and axially di-substituted silicon phthalocyanine 4 was synthesized from 2(3),9(10),16(17),23(24)-tetrakis-{2-[3-(diethylamino)phenoxy]ethoxy}silicon(iv)phthalocyanine dihydroxide 2 with 1-(3-chloropropyl)-4-phenylpiperazine 3 in toluene in the presence of NaH at 120 °C. These complexes were fully characterized by various spectroscopy techniques such as (1)H-NMR, (13)C-NMR, IR, UV-Vis, and MALDI-TOF spectroscopy and elemental analysis as well. Electropolymerization properties of silicon(IV) phthalocyanine complexes were investigated by cyclic and square wave voltammetry. Electrochemical studies reveal that silicon(IV) phthalocyanine complexes were electropolymerized on the working electrode during the anodic potential scan. This study is the first example of electropolymerization of both peripherally tetra and axially di-substituted silicon phthalocyanines on the same molecule.

Preparation of NIR absorbing axial substituted tin(iv) porphyrins and their photocytotoxic properties

“…The axial substitution of metal porphyrins with bulky groups helps to block porphyrin ligands from approaching one another thus preventing aggregation. 12d, [13][14][15][16][17] Heavy diamagnetic metal ions, e.g. Zn 2+ , Sn 4+ , Pd 2+ and In 3+ , are preferred in this context since they promote intersystem crossing (ISC) and hence the energy transfer from the triplet manifold to dioxygen to form singlet oxygen.…”

Synthesis of axially di- and peripherally tetra-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenoxy) group substituted metallophthalocyanines and their electrochemistry

“…[4]. For example, it is used in many fields such as thin film [5], non-linear optics (NLO) [6,7], dye-sensitized solar cells (DSSCs) [8,9], electrochemistry [10][11][12], photodynamic therapy (PDT) [13][14][15]. Although these compounds have a wide range of applications, they have low solubility and a high tendency to aggregate [16].…”

Synthesis, characterization, and α‐glucosidase, cholinesterases, and tyrosinase inhibitory effects of axial substituted silicon and peripheral tetra‐substituted copper (II), manganese (III) phthalocyanines

“…In last years, there have been many studies on the biological studies of phthalocyanine. It has been determined that phthalocyanine compounds substituted with various ligands have antimicrobial, [5] anticancer, [6] antioxidant, [7] anti-glucosidase, [8] anti-tyrosinase, [9] anticarbonic anhydrase, [10] antiurease, [11] anticholinesterase, [12] antixanthine oxidase, [13] electrochemical, [14][15][16] and photodynamic therapy properties. [17] α-Glucosidase, hydrolyze polysaccharides or oligosaccharides to generate glucose units, has a key role in carbohydrate metabolism.…”