Oxazolochlorins. 11. Tuning the dynamic high pH sensing range of [meso-tetraarylporpholactonato]M(II) complexes by variation of the central metal ion, the aryl substituents, and introduction of a β-nitro group

Jill L. Worlinsky, Gloria Zarate, Matthias Zeller, Masoud Ghandehari, Gamal Khalil, Christian Brückner

Research output: Contribution to journalArticle

Abstract

Based on the high pH-sensing ability of [meso-tetrakis(pentafluorophenyl) porpholactonato]-platinum(II), we investigated the influence of the metal (M = Zn(II), Ni(II), Cu(II), Pd(II), Ag(II), Pt(II)), the aryl group (Ar = C 6H5, C6F5), and the presence of a β-NO2 group on the pH sensing range. The syntheses of the novel β-nitroporpholactone derivatives are described, and their regiochemistry deduced by spectroscopic and single crystal X-ray diffraction methods. The UV-vis base titration midpoints for all derivatives were determined in an aqueous solution containing a surfactant, showing that the metal has the least influence, thus identifying a cheaper and easier method to prepare porpholactone M complex-based high pH-sensors. The influence of the pentafluorophenyl groups and the β-nitration were comparable with respect to their ability to increase the nucleophilicity of the porpholactone toward hydroxide, but the optical response for the pentafluorophenyl-substituted derivative were stronger. β-Nitration and pentafluorophenyl-substitution had additive effects.

Original languageEnglish (US)
Pages (from-to)836-849
Number of pages14
JournalJournal of Porphyrins and Phthalocyanines
Volume17
Issue number8-9
DOIs
StatePublished - Jan 1 2013

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Keywords

  • diolchlorins
  • high pH sensing
  • porpholactones
  • tetraarylporphyrin derivatives

ASJC Scopus subject areas

  • Chemistry(all)

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