Synthesis, structure, spectroscopic properties, and electrochemistry of (1,8,15,22-tetrasubstituted phthalocyaninato)lead complexes

Yongzhong Bian, Lei Li, Jianmin Dou, Diana Y.Y. Cheng, Renjie Li, Changqin Ma, Dennis K.P. Ng, Nagao Kobayashi, Jianzhuang Jiang

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)

Abstract

Three (1,8,15,22-tetrasubstituted phthalocyaninato)lead complexes Pb[Pc(α-OR)4] [H2Pc(α-OC5H 11)4 = 1,8,15,22-tetrakis(3-pentyloxy)phthalocyanine; H2Pc(α-OC7H15)4 = 1,8,15,22-tetrakis(2,4-dimethyl-3-pentyloxy)phthalocyanine; H 2Pc(α-OC10H7)4 = 1,8,15,22-tetrakis(2-naphthyloxy)phthalocyanine] (1-3) have been prepared as racemic mixtures by treating the corresponding metal-free phthalocyanines H 2Pc(α-OR)4 (4-6) with Pb(OAc)2· 3H2O in refluxing n-pentanol. The molecular structure of Pb[Pc(α-OC5H11)4] (1) in the solid state has been determined by single-crystal X-ray diffraction analysis. This compound, having a nonplanar structure, crystallizes in the monoclinic system with a P21/c space group. Each unit cell contains two pairs of enantiomeric molecules, which are linked by weak coordination of the Pb atom of one molecule with an aza nitrogen atom and its neighboring oxygen atom from the alkoxy substituent of another molecule, forming a pseudo-double-decker supramolecular structure in the crystals with a short ring-to-ring separation, 2.726 Å, and thus a strong ring-ring π-π interaction. The decreased molecular symmetry for these complexes has also been revealed by the NMR spectra of 1 and 2. The methyl protons of the 3-pentyloxy and 2,4-dimethyl-3-pentyloxy side chains of 1 and 2, respectively, are chemically inequivalent. In addition to the elemental analysis and various spectroscopic characterizations, these compounds have also been electrochemically studied. Two one-electron oxidations and up to five one-electron reductions have been revealed by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods.

Original languageEnglish
Pages (from-to)7539-7544
Number of pages6
JournalInorganic chemistry
Volume43
Issue number23
DOIs
Publication statusPublished - 2004 Nov 15

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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