147699-69-2Relevant academic research and scientific papers
Synthesis of novel push-pull unsymmetrically substituted alkynyl phthalocyanines
Maya, Eva M.,Garcia, Concepcion,Garcia-Frutos, Eva M.,Vazquez, Purificacion,Torres, Tomas
, p. 2733 - 2739 (2007/10/03)
Two families of 'push-pull' phthalocyanines 1-3 having an unusually strong dipole moment have been prepared. The syntheses of unsymmetrically substituted phthalocyanines 1a,b and 2 bearing one or two electron- withdrawing 4-nitrophenylethynyl moieties, respectively, and six alkoxy substituents were performed by combination of a zinc or nickel templated cyclotetramerization and cross-coupling palladium mediated methodologies. In a similar way, the 'push-pull' compounds 3a,b having a reversal substitution pattern, characterized by the presence of one electron-donor 4- (dimethylamino)phenylethynyl unit and six strong acceptor alkylsulfonyl substituents were prepared. The compounds show very large second-order nonlinear optical responses.
A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines
Wohrle,Eskes,Shigehara,Yamada
, p. 194 - 196 (2007/10/02)
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.
