Phenyl-substituted planar binuclear phthalo- and naphthalocyanines: synthesis and investigation of physicochemical properties

Dodeca-phenyl-substituted planar binuclear phthalocyanine magnesium complexes with an extended π-conjugation system were synthesized with high yields. Two approaches to the extension of the π-system were presented: extension of an aromatic bridge or a peripheral π-system. A maximum of near-IR absorption at 972 nm was observed in the case of the planar binuclear naphthalocyanine sharing a common benzene ring. Binuclear phthalo- and naphthalocyanines were characterized by high resolution MALDI-TOF mass spectrometry, UV/Vis/NIR and 1H NMR spectroscopy. DFT modeling of the structure and chemical shift GIAO calculations were made. The formation of nanoaggregates in a solid film was proven using AFM. The electrochemical properties of binuclear naphthalocyanine complexes were investigated for the first time.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Planar binuclear phthalocyanines with an extended π-system are obtained. ► The extension of an aromatic bridge or a peripheral π-system is presented. ► A maximum of near-IR absorption at 972 nm is observed. ► The formation of nanoaggregates in a solid film is proven using AFM. ► The electrochemical properties of phthalo- and naphthalocyanines are investigated.