10.1016/j.dyepig.2011.10.012
The study explores the synthesis and properties of phenyl-substituted planar binuclear phthalocyanine and naphthalocyanine magnesium complexes with extended π-conjugation systems. The researchers synthesized these compounds using various chemical reactions, including Suzuki-Miyaura cross-coupling and condensation reactions. Key chemicals involved include pyromellitonitrile, 2,3,6,7-tetracyanonaphthaline, 1,2-dicyano-4,5-diphenylbenzene, and 6,7-diphenylnaphthalene-2,3-dicarbonitrile, which served as starting materials or intermediates. Magnesium acetate was used as a metal source, and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) was employed as a base to facilitate the formation of the binuclear complexes. The synthesized compounds were characterized using techniques such as MALDI-TOF mass spectrometry, UV/Vis/NIR spectroscopy, and 1H NMR spectroscopy. The study investigates the correlation between the extension of the aromatic system and the position of absorption in the near-IR region, as well as the electrochemical properties of these binuclear complexes. The results show that extending the π-system leads to significant red-shifts in absorption maxima, with the Q2-band of a binuclear naphthalocyanine complex reaching up to 972 nm. The study also examines the aggregation behavior of these compounds in different solvents and their redox properties using cyclic voltammetry and square-wave voltammetry.