214150-97-7

Upstream product

• 111-88-6 Octanethiol 
• 139152-08-2 4,5-dichlorophthalonitrile 
• 86938-64-9 4,5-dibromobenzene-1,2-dicarbonitrile 
• 175883-98-4 4,5-diiodobenzene-1,2-dicarbonitrile 

Downstream Products

• 216771-94-7 1,2-dicyano-4,5-bis(octylsulfonyl)benzene 

Relevant academic research and scientific papers

Phthalocyanine synthesis in ionic liquids: Preparation of differently substituted phthalocyanines in tetrabutylammonium bromide

A series of alkylthio, alkoxy, and phenoxy phthalonitriles have been prepared by nucleophilic substitution reactions on suitable phthalonitrile precursors in molten tetrabutylammonium bromide. This readily available and inexpensive ionic liquid can also b

Predominant effect of connecting atom and position of substituents on azomethine nitrogens' basicity in phthalocyanines

The basicity of azomethine nitrogens was studied on a series of phthalocyanines (Pcs) that differed in a position of substituent, i.e. peripherally (β-series) and non-peripherally substituted Pcs (a-series), and in a type of substituent (alkylsulfanyl, alkyloxy or alkyl). Appropriate 3,6-or 4,5-disubstituted phthalonitriles were prepared either by nucleophilic substitution or by Negishi coupling. Target zinc Pcs were synthesized by Linstead method. The basicity was studied by the mean of absorption and 1H NMR spectroscopies in chloroform upon titration with trifluoroacetic acid. Equilibrium constants (log K) indicated significant difference within the series. Basicity decreased as follows: α-alkyloxy > α-alkylsulfanyl > β-alkyloxy > β-alkyl > β-alkylsulfanyl ~ α-alkyl with log K higher than 7 down to 2.6 M-1. Increased basicity of a-alkyloxy and a-alkylsulfanyl Pcs is caused by the stabilization of trapped hydrogen at azomethine nitrogen via hydrogen bonding and van der Waals interactions, respectively. The basicity of b-series clearly correlated with the electronic effects of substituents. 1H NMR studies confirmed the possibility of the weak bonding interactions in a-alkyloxy and α-alkylsulfanyl Pcs, however, the position of the 1H NMR signal of azomethine-NH proton was even more influenced by the electronic effects of present substituents than by the weak interactions.

Trapping fullerenes with jellyfish-like subphthalocyanines

Six electronically different concave-shaped subphthalocyanines (SubPcs) have been prepared for testing the structural factors governing fullerenes encapsulation. Thus, the supramolecular interaction of SubPcs with C 60 and C70 fuller

Liquid crystalline octasubstituted lead(ii) phthalocyanines: Effects of alkoxy and alkylthio substituents on film alignment and electrical properties

Octasubstituted lead(ii) phthalocyanines containing alkylthio- and alkoxy- groups in peripheral positions have been synthesized and characterized using 1H and 13C NMR, UV-Vis, IR and mass spectroscopies as well as elemental analysis. The mesogenic properties of the octasubstituted lead(ii) phthalocyanines have been investigated by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction. The sandwich structures ITO/PbPc/In were prepared to investigate the J(V) characteristics of thin films of these molecules. The dissimilar behavior of the films before and after heat-treatment is expected to result in changing the alignment inside the columnar stacking of the molecules in the films.

Halide effect in electron rich and deficient discotic phthalocyanines

A series of discotic octa- and tetra-alkylthio substituted phthalocyanines containing four Cl, Br, I atoms or twelve fluorine atoms have been prepared. All compounds display columnar mesomorphism as confirmed by polarized optical microscopy, thermal analysis, and variable temperature X-ray diffraction. Phthalocyanines containing halide atoms do not crystallize but form glassy or partially crystalline hexagonal columnar phases. Glass transition temperatures increase with increasing size of the halide atoms and with decreasing length of the alkyl chains. In contrast, all octa- and tetra-alkylthio substituted phthalocyanines crystallize and octa-substituted derivatives with aliphatic chain lengths of C5-7 exhibit tilted (rectangular) columnar mesophases. Cyclic and differential pulse voltammetry, UV-Vis spectroscopy, and quantum chemical calculations at the DFT level have been employed to determine frontier orbital energies of all synthesized and some reference phthalocyanines. Octa- and tetra-alkylthio substituted phthalocyanines are typical p-type semiconductors and the introduction of four Cl, Br, or I atoms lowers frontier orbital energies by only up to 0.1 eV and the optical gap by up to 0.03 eV. A significant decrease in LUMO energy by 0.5 eV to about -4 eV is observed for the fluorinated phthalocyanine, which is a value right at the border of organic n-type semiconductors that may be stable in air.

Solvent-free synthesis of soluble, near-IR absorbing titanyl phthalocyanine derivatives

Solvent-free synthesis of a series of alkylthio-substituted titanyl phthalocyanine (TiOPc) derivatives starting from the corresponding phthalonitriles (Pn) is reported. This methodology eliminates the formation of the unmetalated phthalocyanine (H2/

Photophysical and photochemical properties of Ni(II), Pd(II) and Pt(II) aryloxo and alkylthio derivatised phthalocyanine

Several aryloxo (3a-6a and 3b-6b) and alkylthio (3d and 3e) derivatised phthalocyanines were synthesized, characterized and the photochemical and photophysical properties investigated along with those of the previously reported (3c-5c, 4d, 5d, 4e and 5e)

Discotic liquid crystals of transition metal complexes 29: Mesomorphism and charge transport properties of alkylthio-substituted phthalocyanine rare-earth metal sandwich complexes

A series of bis[octakis(alkylthio)phthalocyaninato]rare-earth-metal(III) discotic compounds, [(CnS)8Pc]2M (M=Eu(III), Tb(III), Lu(III); n=8, 10, 12, 14, 16, 18), has been synthesized. The mesomorphic and supramolecular str

Discotic liquid crystals of transition metal complexes 27: Supramolecular structure of liquid crystalline octakisalkylthiophthalocyanines and their copper complexes

A series of octakisalkylthiophthalocyanines, (C(n)S)8PcH2 (n = 8, 10, 12, 16), and their copper(II) complexes, (C(n)S)8PcCu (n = 8, 10, 12, 16), have been synthesized. Their mesomorphism and supramolecular structures have

Synthesis and nonlinear optical, photophysical, and electrochemical properties of subphthalocyanines

Novel boron(III) subphthalocyanines (SubPcs) soluble in organic solvents containing a variety of donor and acceptor substituent groups have been synthesized by boron trihalide-induced cyclotrimerization of adequately substituted derivatives of phthalonitr