(Phthalocyaninato)copper(II) complexes fused with different numbers of 15-crown-5 moieties - Synthesis, spectroscopy, supramolecular structures, and the effects of substituent number and molecular symmetry

Ning Sheng, Yuexing Zhang, Hui Xu, Meng Bao, Xuan Sun*, Jianzhuang Jiang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Symmetrical (phthalocyaninato)copper(II) complexes Cu(Pc′) [Pc′ = Pc(15C5), Pc(opp-15C5)2, Pc(adj-15C5)2, Pc(15C5) 3; Pc = unsubstituted phthalocyaninate, Pc(15C5) = 2,3-(15-crown-5)phthalocyaninate, Pc(opp-15C5)2 = 2,3,16,17-bis(15-crown-5)phthalocyaninate, Pc(adj-15C5)2 = 2,3,9,10-bis(15-crown-5)phthalocyaninate, Pc(15C5)3 = 2,3,9,10,16,17-tris(15-crown-5)phthalocyaninate] (2-5) have been prepared by the reaction of corresponding heteroleptic bis(phthalocyaninato)europium complexes Eu(Pc)(Pc′) [Pc′ = Pc(15C5), Pc(opp-15C5)2, Pc(adj-15C5)2, Pc(15C5)3, Pc(15C5)4; Pc = unsubstituted phthalocyaninate] with Cu(OAc)2 in dry dmf at 100°C. For the purpose of comparative studies, the symmetrical counterparts CuPc (1) and CuPc(15C5)4 [Pc(15C5)4 = 2,3,9,10,16,17,24, 25-tetrakis(15-crown-5)phthalocyaninate] (7) have also been prepared. These monomeric complexes have been characterized by spectroscopic methods in addition to elemental analysis. Having a series of closely related phthalocyanines with a different number and/or disposition of 15-crown-5 groups at the peripheral positions, the effects of 15-crown-5 substituent number and molecular symmetry on the electronic absorption spectra, infra-red (IR) spectra, and supramolecular structure formation induced by K+ ions have been investigated. Systematic studies on the formation of dimeric supramolecular structures of the series of monomers 2-6 reveal and confirm the previously proposed two-step three-stage process of K+-induced dimerization of phthalocyanines with three or four 15-crown-5 moieties.

Original languageEnglish (US)
Pages (from-to)3268-3275
Number of pages8
JournalEuropean Journal of Inorganic Chemistry
Issue number20
DOIs
StatePublished - Aug 2 2007

Keywords

  • Crown ether
  • Molecular symmetry
  • Phthalocyanines
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Inorganic Chemistry

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