Enrichment of solubility by esterification: Metal-free and metallo-porphyrazines with polyfluorinated units

Simsek T., Gonca E.

TRANSITION METAL CHEMISTRY, vol.38, no.1, pp.37-43, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 38 Issue: 1
  • Publication Date: 2013
  • Doi Number: 10.1007/s11243-012-9658-4
  • Journal Name: TRANSITION METAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.37-43
  • Çanakkale Onsekiz Mart University Affiliated: No

Abstract

Metal-free and metallo-porphyrazines (M = 2H, Mg, Cu, Zn or Co) carrying eight hydroxypropylsulfanyl units at the peripheral positions were synthesized from 2,3-bis(3-hydroxypropylthio)maleonitrile. The reactivity of the hydroxypropyl units was demonstrated by the esterification of porphyrazine derivatives with 3,5-bis(trifluoromethyl)benzoic acid in the presence of dicyclohexylcarbodiimide and toluene-p-sulfonic acid. The symmetrical porphyrazine derivatives with eight ester units were soluble in common organic solvents such as chloroform, dichloromethane, THF, acetone, and toluene and insoluble in water and n-hexane. The complexes were characterized by several spectroscopic methods.