Synthesis and spectroscopic characterisation of non‐aggregated novel axially 4‐{2‐[3‐(diethylamino)phenoxy]ethoxy} and crown ether substituted silicon phthalocyanines

Abstract

This paper describes the synthesis and spectroscopic characterisation of a range of new axially disubstituted silicon phthalocyanines, with 4‐{2‐[3‐(diethylamino)phenoxy]ethoxy}, 4‐(1,4,7,10‐tetraoxacyclododecan‐2‐ylmethoxy) and 4‐(1,4,7,10,13,16‐hexaoxacyclooctadecan‐2‐ylmethoxy) groups as axial ligands. These axially disubstituted silicon phthalocyanine complexes were synthesised for the first time here. The newly synthesised silicon phthalocyanines were characterised by ultraviolet–visible, infrared, proton and carbon nuclear magnetic resonance spectroscopy, electrospray ionisation mass spectrometry and elemental analysis. The aggregation behaviour of these compounds was investigated in different concentrations of chloroform and the effects of various organic solvents on the absorption spectra were studied.

Catalytic Oxidation of Benzyl Alcohol to Efficiently Synthesize Amide by (−CF3) Substituted Copper Phthalocyanine Based Composite Catalyst

“…The modification of different substituents on the periphery can change its conjugation structure. [36][37][38][39][40][41][42][43][44][45][46][47] In recent years, the synthesis of phthalocyanines through metal coordination has attracted more and more attention in the field of catalysis. [48][49][50][51][52][53] However, due to its big ring conjugated structure, it is easy to agglomerate, which significantly diminishes the catalytic impact.…”

Non-aggregated axially disubstituted silicon phthalocyanines bearing electropolymerizable ligands and their aggregation, electropolymerizaton and thermal properties

“…[16][17][18] However, the poor solubility and aggregation of phthalocyanines limits their applications. [21][22][23][24][25][26] The axial substitution of phthalocyanines can strongly influence the essential parameters of a phthalocyanine, such as its solubility, aggregation behavior, electronic absorption, photophysical, photochemical and electrochemical properties. 19 Also, aggregation is an unfavourable property of phthalocyanines.…”

“…In recent years, in order to improve the solubility of phthalocyanines, many axially disubstituted silicon phthalocyanine complexes have been synthesized. [21][22][23][24][25][26] The axial substitution of phthalocyanines can strongly influence the essential parameters of a phthalocyanine, such as its solubility, aggregation behavior, electronic absorption, photophysical, photochemical and electrochemical properties. 27 Axially disubstituted silicon phthalocyanines display very attractive electrochemical properties.…”

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

“…[23][24][25][26][27][28] On the other hand, to overcome the aggregation problem of phthalocyanines, many axially disubstituted silicon phthalocyanine complexes have been synthesized. [29][30][31][32] Axial substitution is an attractive feature for phthalocyanines because of the following reasons: (i) having a macrocycle with different substituents prevents aggregation and increases the solubility of phthalocyanines, (ii) the ligands can be highly functionalized, and (iii) silicon phthalocyanines are resistant in chemical treatments. 33 Although there are many examples of non-peripherally but axially substituted silicon phthalocyanines, only a few studies about peripherally or non-peripherally as well as axially substituted silicon phthalocyanines on the same molecule are known in the literature.…”