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Templated tetramerization of dicyanobenzenes to form mixed porphyrinato and phthalocyaninato rare earth(III) triple-decker complexes

Key Laboratory for Colloid and Interface Chemistry of State Education Ministry, Department of Chemistry, Shandong University, Jinan 250100, P. R. China

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Jianzhuang Jiang

Key Laboratory for Colloid and Interface Chemistry of State Education Ministry, Department of Chemistry, Shandong University, Jinan 250100, P. R. China

CIDC, School of Physical and Chemical Sciences, Queensland University of Technology, G. P. O. Box 2434, Qld. 4001, Australia

State Key Laboratory of Materials Chemistry and Applications, Peking University, Beijing 100871, P. R. China

Corresponding author, fax: +86 531 856 5211.

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Xuegui Cui

Key Laboratory for Colloid and Interface Chemistry of State Education Ministry, Department of Chemistry, Shandong University, Jinan 250100, P. R. China

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, and

Dennis P. Arnold

CIDC, School of Physical and Chemical Sciences, Queensland University of Technology, G. P. O. Box 2434, Qld. 4001, Australia

Corresponding author, fax: +61 7 3864 1804.

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https://doi.org/10.1142/S1088424602000415Cited by:13 (Source: Crossref)

Abstract

Heteroleptic porphyrinato/phthalocyaninato rare earth(III) triple-decker compounds M₂(Por)₂(Pc') (1a-4a) and M₂(Por)(Pc')₂ (1c-4c) (M = Eu, Tb; Por = TDOPP, Pc' = OOPc or Por = TpClPP, Pc' = Pc where H₂(TDOPP) = 5,10,15,20-tetrakis(4-n-dodecyloxyphenyl)porphyrin, H₂[OOPc] = 2,3,9,10,16,17,23,24-octakis(n-octyloxy)phthalocyanine, H₂(TpClPP) = 5,10,15,20-tetrakis(4-chlorophenyl)porphyrin, H₂(Pc') = general phthalocyanine, and H₂(Pc) = unsubstituted phthalocyanine) were obtained by the cyclic tetramerization of the corresponding dicyanobenzenes 7 using monoporphyrinato rare earth(III) acetylacetonates M(Por)acac as templates with catalysis by the organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Double-decker complexes M(Por)(Pc') (M = Eu, Tb; Por = TDOPP, Pc' = OOPc or Por = TpClPP, Pc' = Pc) (1b-4b) were isolated as side products. For the purpose of comparative study, homo- and hetero-dinuclear rare earth triple-deckers with one porphyrinato and two phthalocyaninato ligands M₂(Por)(Pc')₂ (1c, 2c) (M = Eu, Tb; Por = TDOPP, Pc' = OOPc) and (Por)M(Pc')M'(Pc')(M ≠ M' = Eu, Tb) (5c, 6c) were also prepared using the raise-by-one-story method. The complexes were characterized by UV-vis, near-IR, IR and mass spectra. The comparison between ¹H NMR spectra of the two series of triple-decker compounds a and c, and also between the substituted phthalocyanine- and unsubstituted phthalocyanine-containing europium triple-deckers, renders it possible to assign the aromatic proton signals unambiguously.

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