116453-83-9Relevant academic research and scientific papers
Synthesis and spectral characteristics of phthalocyanines of unsymmetrical structure containing fragments of 3,6-didecyloxyphthalonitrile and 2-methyl-5,6-dicyanobenzimidazole
Galanin,Kudrik,Shaposhnikov
, p. 225 - 230 (2008)
By alkylation of 3,6-dihydrooxyphthalonitrile with 1-bromodecane and by reaction of 4,5-diaminophthalodinitrile with acetic acid were synthesized respectively 3,6-didecyloxyphthalonitrile (A) and 2-methyl-5,6- dicyanobenzimidazole (B). The random condensation of the dinitriles obtained provided unsymmetrical phthalocyanines of A 3 B, AABB, and AB 3 type. Their spectral characteristics were investigated.
Discotic liquid crystals of transition metal complexes, 55 : Novel chlorine-substituted phthalocyanine derivatives showing mesomorphism and low HOMO energy level
Yatabe, Masashi,Kajitani, Akio,Yasutake, Mikio,Ohta, Kazuchika
, p. 32 - 45 (2018)
We have synthesized a series of novel phthalocyaninato copper(II) (abbreviated as PcCu) compounds, 1,4,8,11,15,18,22,25-octakisalkoxy-2,3,9,10,16,17,23,24-octachloro-phthalocyaninato copper(II) (abbreviated as (α-CnO)8(β-Cl)8PcCu (4a-4d): n = 6 (a), 8 (b), 10 (c) and 12 (d)) and, for comparison, another series of PcCu compounds, 1,4,8,11,15,18,22,25-octakisalkoxyphthalocyaninato copper(II) (abbreviated as (α-CnO)8PcCu (1a-1d)). The PcCu derivatives 1a-1d are substituted by alkoxy chains only at the α positions (1,4,8,11,15,18,22,25). On the other hand, the PcCu derivatives 4a-4d are substituted by alkoxy chains at the α positions and chlorine atoms at the β positions (2,3,9,10,16,17,23,24). We have investigated the influence of chlorine atoms substituted at the β positions of the Pc ring on mesomorphism, spectroscopic and electronic properties for these two series of PcCu derivatives 1 and 4 by using a polarizing optical microscope, DSC, temperature-variable small angle X-ray diffractometer, a UV-Vis spectrophotometer and cyclic voltammetry. Each of the derivatives 1a-1d is crystalline without showing mesomorphism. On the other hand, each of the chlorine-substituted PcCu derivatives 4a-4d shows plural phase transitions, and the longer chain-substituted PcCu derivatives 4c-4d show a rectangular ordered columnar [Colro(P2m)] mesophase. Furthermore, we have revealed that each of the PcCu derivatives 4a-4d shows a Q-band in the near-infrared region and a lower HOMO energy level than conventional phthalocyanine derivatives.
Octa-alkoxy Phthalocyanine and Naphthalocyanine Derivatives: Dyes with Q-band Absorption in the Far Red or Near Infrared
Cook, Michael J.,Dunn, Adrian J.,Howe, Steven D.,Thomson, Andrew J.,Harrison, Kenneth J.
, p. 2453 - 2458 (2007/10/02)
The lithium alkoxide-catalysed cyclic tetramerisation of various 3,6-dialkoxy-4,5-dichlorophthalonitriles, 1,4-dialkoxynaphthalene-2,3-dicarbonitriles and 3,6-dialkoxyphthalonitriles to give the corresponding metal-free octa-alkoxyoctachlorophthalocyanines, octa-alkoxynaphthalocyanines and octa-alkoxyphthalocyanines is described.An unexpected trans-alkoxylation reaction occurs during the cyclisation of the first two series of precursors.Metal-free phthalocyanines and naphthalocyanines have been converted into derivatives containing various metal ions.Compounds show Q-band absorption in the region 739-862 nm in toluene solution.The fluorescence spectra of selected examples are reported.The solubility of some of the compounds has been measured in a formulation of liquid crystal materials.
