The synthesis of tetra and octa perfluoroalkyl substituted zinc and metal free phthalocyanines ( ZnPc and H 2 Pc ) are reported. The compounds 1–5 have been prepared by nucleophilic substitution of 4-nitrophthalonitrile with 1H,1H,2H,2H-perfluorooctanethiol, 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol, 1H,1H-perfluorotetradecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol, respectively. The compounds 6–8 have been prepared by the reaction of 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol with 4,5-dichlororphthalonitrile, respectively. The compound 9 with thia-bridge has been synthesized from 4,5-dichlororphthalonitrile. Zinc and metal free phthalocyanines were obtained from the corresponding phthalonitrile derivatives. All compounds were characterized by using mass, 1 H , 19 F NMR, UV-vis and FT-IR as well as elemental analysis. Tetra substituted Zn ( II ) phthalocyanines are slightly soluble only in THF (Compound 4a and 7a are insoluble) but metal free phthalocyanines are not soluble. Octa substituted Zn ( II ) and metal free phthalocyanine are soluble in polar solvents such as THF and DMSO.
报告了四和八全氟烷基取代锌和无金属酞菁(ZnPc 和 H 2 Pc)的合成。1-5 号化合物分别由 4-硝基邻苯二腈与 1H,1H,2H,2H-全氟辛硫醇、1H,1H,2H,2H-全氟癸-1-醇、1H,1H-全氟癸-1-醇、1H,1H-全氟十四烷-1-醇和 1H,1H-全氟-3,6,9-三氧杂十三烷-1-醇发生亲核取代反应制备而成。化合物 6-8 分别由 1H,1H,2H,2H-全氟-1-癸醇、1H,1H-全氟-1-癸醇和 1H,1H-全氟-3,6,9-三氧杂十三烷-1-醇与 4,5-二氯邻苯二甲腈反应制备而成。带有噻桥的化合物 9 是由 4,5-二氯间苯二甲腈合成的。从相应的酞腈衍生物中获得了锌和无金属酞菁。所有化合物都通过质量、1 H、19 F NMR、UV-vis 和 FT-IR 以及元素分析进行了表征。四取代 Zn ( II ) 酞菁仅微溶于四氢呋喃(化合物 4a 和 7a 不溶),但不溶于无金属的酞菁。八取代 Zn ( II ) 和无金属酞菁可溶于 THF 和 DMSO 等极性溶剂。