Fusing phthalocyanine and porphyrin together: Unprecedented co-planar ring-fused diazaphthalocyaninato-porphyrin dimers

Kang Wang, Dong Dong Qi, John Mack, Hai Long Wang, Wen Jun Li, Yong Zhong Bian, Nagao Kobayashi, Jian Zhuang Jiang

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

An unprecedented ring-fused co-planar diazaphthalocyaninato-porphyrin dimer H 4{[(DAPc(OC 4H 9) 6] [TC1PP]} (where DAPc (OC 4H 9) 6is the dianion of 2,3,9,10,16,17-hexa (butyloxy)-22,25-diazaphthalocyanine, and TC1PP is the dianion of 5,10,15,20-tetra(4-ch1oro)porphyrin) (1) was synthesized by mixed cyclic tetramerization of 5,10,15,20-tetrakis(4-chlorophenyl)-2′,3′-dicyanopyrazino[2,3-β] porphyrin with 4,5-di(butyloxy)phthalonitrile in the presence of lithium in refluxing n-pentanol followed by treatment with acetic acid. Reaction of the metal free dimer with Zn(OAc) 2·2H 2O in DMF and toluene led to the isolation of a bimetallic zinc(II) complex Zn 2{[(DAPc (OC 4H 9) 6] [(TClPP)]} (2). The binuclear and mixed tetrapyrrole ring nature of the structure was clearly demonstrated by a series of characterization methods including mass spectrometry and NMR spectroscopy. The Q band region of the electronic absorption and magnetic dichroism (MCD) spectra provide evidence for significant intramolecular interaction between the phthalocyanine and porphyrin chromophores. Theoretical calculations provide further support for this.

Original languageEnglish
Pages (from-to)1779-1789
Number of pages11
JournalChinese Journal of Inorganic Chemistry
Volume28
Issue number9
Publication statusPublished - 2012

Keywords

  • Conjugated dimer
  • Mixed binuclear
  • Phthalocyanine
  • Porphyrin
  • Tetrapyrrole

ASJC Scopus subject areas

  • Inorganic Chemistry

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