Synthesis of organo-soluble metallophthalocyanines bearing electron-withdrawing substituents

Abstract

ABSTRACT:The syntheses of organo-soluble metallophthalocyanines having sulfo-and sulfonamido-electronwithdrawing substituents are reported. The simple cation exchange of the readily available tetrasodium salt of metallo-sulfophthalocyanines 1 (M = Ni, Co, Fe, Cr) by alkylammonium salts afforded the sulfophthalocyanines 2 and 3 in good yields. Complexes 2 featuring two long C18 alkyl chains are only soluble in organic solvents while tetrabutylammonium counter ions exhibit a dual solubility in both organic solvents and water for compounds 3. The tetrasulfonamidophthalocyanine complexes 5-7 with four C8, four C18 or eight C8 alkyl chains have been obtained after chlorination of the sulfophthalocyanines 1 leading to the chlorosulfonyl derivatives 4, followed by reaction with various substituted amines. The synthesis of the chromium precursors with tetrasulfo and tetrachlorosulfonyl substituents is also described.

Oxygen reduction reaction at MWCNT-modified nanoscale iron(ii) tetrasulfophthalocyanine: remarkable performance over platinum and tolerance toward methanol in alkaline medium

“…28 The typical stretching bands of aromatic C]C groups can be seen at 1637 cm À1 . 18,27,28 The nanoFeTSPc displayed additional bands (encircled in broken lines) with the intense peak of the C-H group of alkylammonium chains around 2919 cm À1 , 18 intense peaks around 3100 cm À1 and 995 cm À1 due to olenic groups, and peaks of methyl and methylene groups around 2980-2850 cm À1 and 1480 cm À1 . 28 These results conrm the modication of the structure of the pristine FeTSPc with the hydrophobic long-chain alkane of the CTAB molecule.…”

“…[15][16][17] The high solubility of FeTSPc has limited its application in heterogeneous catalysis such as the ORR. In this work, we have produced an organo-soluble nanostructured FeTSPc incorporating longchain alkane of the CTAB via coordinate covalency with a slight modication of a similar procedure by Sanchez et al 18 To explore the impact of surface functional groups on MWCNT support, this organo-soluble nanostructured FeTSPc (nanoFeTSPc) was subsequently integrated on sulfonate-functionalised (s-MWCNT) and carboxyl/hydroxyl-functionalised MWCNTs (o-MWCNT). The choice for MWCNTs as a support is based on its high conductivity, and functionalising them with carboxylic (COOH) 19,20 and sulfonic groups (SO 3 H) [21][22][23] will enhance their dispersibility in aqueous media.…”

Synthesis and high ranked NLT properties of new sulfonamide-substituted indium phthalocyanines

“…Peripheral functionalization of a phthalocyanine with appropriate groups can afford new derivatives with increased solubility in apolar or polar organic solvents or even in aqueous media. Sulfonated phthalocyanines, both in the sulfonato and sulfonamide forms, are already described in the literature [39,40]. Some of these compounds show potential application in photodynamic therapy [11][12][13] or in the production of other materials, due to their interesting photoconductive properties [6].…”

Sulfonamide-substituted iron phthalocyanine: design, solubility range, stability and oxidation of olefins

“…Substitution patterns including or based on sulfonamide function are scarcely used for phthalocyanines: tetrasulfophthalocyanines were amidified by octylamine, 15 and tetrasulfonamide Co(II) phthalocyanine was used for the catalytic oxidative sweetening of LPG. 16 Amidified tetrasulfo phthalocyanines proved to be as well good NO x sensors, thanks to the possible intermolecular interactions with nitrogen dioxide.…”