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Solid-Phase Synthesis of Asymmetrically Substituted "AB3-Type" Phthalocyanines.

  作者 Erdem, S. Sibel;Nesterova, Irina V.;Soper, Steven A.;Hammer, Robert P.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-13;  页码  5003-5007  
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[摘要]Synthesis of phthalocyanines with asym. substitution on the periphery is often difficult due the problems in purifn. of the phthalocyanine mixts. obtained. Using a poly(ethylene glycol) (PEG)-based support with a Wang-type linker, the authors have developed the synthesis of monohydroxylated, oligoethylene glycol substituted phthalocyanines using an amidine-base-promoted phthalonitrile tetramerization reaction. The use of a hydrophilic support allows sym. phthalocyanine product formed in soln. to be readily and completely removed by washing while leaving the AB3 product on the support. Acid cleavage with 10% HO2CCF3 provides the pure unsym. substituted Pc. This method was applied to several metallo Pcs. Addnl., methods to avoid premature reactions on-resin that give A2B2 products are provided.

 
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