Rapid and efficient synthesis of metallophthalocyanines in ionic liquid

Abstract

Metallophthalocyanines have been synthesized in a very short time with excellent yields in the presence of tetrabutylammonium bromide ( TBAB ) as an ionic liquid at 185 °C. The ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency.

Fast Hydrogen Atom Abstraction by a Hydroxo Iron(III) Porphyrazine

“…14 Complex 2 showed an appropriate molecular ion in the ESI MS (Figure S1) and sharp peaks in the 1 H NMR with similar chemical shifts to those of Zn II PyPz (Figure S2). 15 The EPR spectrum of 2 showed no signals (Figure S3).…”

Synthesis of substituted phthalocyanines

“…In the majority of cases, chlorine-containing phthalonitriles were used as the key precursors in the cyclotetramerization reaction. It has been recently shown 108 that yields of chlorinated transition-metal phthalocyanines from chlorinated anhydrides can be improved by using an ionic liquid as the reaction media. In general, introduction of chlorine atoms into the phthalocyanine core increases the first oxidation potential of the respective phthalocyanine, 109 and changes the color of the target compounds from blue to green.…”

Synthesis and Photophysical, Electrochemical and Theoretical Study of Thi­azole‐Annelated Phthalocyanines

“…HRMS analyses were performed with an ORBITRAP VELOS PRO instrument, Thermo Scientific with APPI ionisation by using a krypton lamp and methanol/water (1:1) solution as dopant. 1 H and 13 C NMR spectra were recorded with a Varian NMR System 300 (300 MHz) spectrometer or with a Varian NMR System 600 (600 MHz) in CDCl 3 or [D 6 ]DMSO with tetramethylsilane (TMS) as internal standard. Elemental analyses were measured with a Carlo-Erba instrument, model 1106 SCI-ENCE and Vario MICRO CUBE analyser (Elementar).…”

“…[4] Phthalocyanines with annelated heterocycles are commonly prepared through the use of appropriately substituted precursors, namely iminoisoindoles, phthalimides, and phthalonitrile derivatives. Although there are many synthetic protocols available for the preparation of substituted Pcs, [5][6][7] cyclotetramerisation of substituted phthalonitriles under basic conditions is generally preferred.…”