Synthesis, characterization and properties of 1,11,15,25-tetrahydroxy-4,8,18,22-bis(bridging butanedioic acid)phthalocyanine copper

• We have synthesized novel phthalocyanine derivative bearing peripheral 1,11,15,25-tetrahydroxy-4,8,18,22-Bis(bridging butanedioic acid)substituent.
• The newly synthesized phthalocyanine copper was soluble in chloroform, THF, DMSO and DMF, and less soluble in i-PrOH.
• In cyclic voltammetry experiments, 1,11,15,25-tetrahydroxy-4,8,18,22-Bis(bridging butanedioic acid)phthalocyanine copper displayed three macrocycle-centred redox processes; two reduction and one oxidation processes.
• CuPc is most likely to be made the yellow light-emitting device on the results of fluorescence spectra. The NIR EL spectra displayed the characteristic spectra of CuPc with a band near 1098 nm. The OLED device could emit in visible (yellow or blue-yellow) region as well as NIR region.

A novel copper phthalocyanine complex with bridging butanedioic acid moieties, 1,11,15,25-tetrahydroxy-4,8,18,22-bis(bridging butanedioic acid) phthalocyanine copper, is reported. This complex is soluble in chloroform, THF, DMSO and DMF, and sparingly soluble in i-PrOH. The compound is characterized by elemental analysis, IR, 1H NMR and UV/Vis spectroscopies and MALDI–TOF–MS. Cyclic voltammetry showed that the complex exhibited well-defined ring-based reduction and oxidation processes. NIR OLEDs containing tris-(8-hydroxyquinoline) aluminum doped with the copper phthalocyanine complex were fabricated. Room-temperature electroluminescence was observed near 1098 nm originating from the transition from the first excited singlet state to the ground state.

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