147699-65-8

Upstream product

• 139152-08-2 4,5-dichlorophthalonitrile 
• 123-31-9 hydroquinone 
• 942-06-3 4,5-dichlorophthalic anhydride 
• 15997-89-4 4,5-dichlorophthalimide 
• 859299-66-4 dimethyl 4,5-dibromo-1,2-benzenedicarboxylate 
• 162607-23-0 2,5-dimethylthien-3-ylboronic acid 
• 147699-62-5 4,5-dichloro-1,2-benzenedicarboxamide 
• 56962-08-4 4,5-dichlorophthalic acid 

Downstream Products

• 1209011-43-7 C₅₀H₅₆N₂O₄ 
• 613222-53-0 C₆₂H₄₈N₂O₈ 
• 1209011-44-8 C₉₄H₁₁₂N₂O₈ 
• 1188517-58-9 4,5-bis(4-(6-(triisopropylsilyl)hex-5-ynyloxy)phenoxy)phthalonitrile 
• 1188517-60-3 4,5-bis(4-(hex-5-ynyloxy)phenoxy)phthalonitrile 

Relevant academic research and scientific papers

Octathienyl/phenyl-substituted zinc phthalocyanines J-aggregated through conformational planarization

A novel family of thiophene-decorated phthalocyanines (M-TPcs) was efficiently synthesized, during which the key intermediate of these compounds was purified through a chemical approach. In the optimized geometries of M-TPcs, the peripherally linked thiophene rings are tilted from the Pc core, which oppose aggregation considering the mutual steric hindrance. However, Zn-TPc formed J-aggregates in many solvents while Ni-TPc and Cu-TPc did not. Octaphenyl-substituted zinc Pc (Zn-PPc) showed similar J-aggregation behavior as Zn-TPc. This unusual J-aggregation was attributed to the conformational planarization of the corresponding molecules.

A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines

4,5-Dichloro-1,2-dicyanobenzene (5) was prepared in an overall yield of 49% from 4,5-dichloro-1,2-benzenedicarboxylic acid (1). The reactions of 5 with phenols, thiophenol and 1-propanethiol led in a nucleophilic displacement reaction to the 4,5-bis(aryloxy)-, 4,5-bis(phenylthio)- and 4,5-bis(propylthio)-1,2-dicyanobenzenes 6 which were converted in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in high yields to octasubstituted phthalocyanines (tetrabenzoporphyrazines) 7. Some compounds 7 contain eight free phenolic, carboxylic acid or pyridyl groups.