Perylene diimide-appended mixed (phthalocyaninato)(porphyrinato) europium(III) double-decker complex: Synthesis, spectroscopy and electrochemical properties

Publication year: 2011
Source: Dyes and Pigments, Volume 91, Issue 2, November 2011, Pages 99-104

Shuai, Dong , Xianyao, Zhang , Yang, Zhou , Jianzhuang, Jiang , Yongzhong, Bian

Treatment of sandwich-type mixed (phthalocyaninato)(porphyrinato) metal complex [HEuIII{Pc(α-3-OC5H11)4}{TriBPP(NH2)}] (3) [Pc(α-3-OC5H11)4=1,8,15,22-tetrakis(3-pentyloxy)-phthalocyaninate, TriBPP(NH2)=5,10,15-tris(4-tert-butylphenyl)-20-(4-aminophenyl)porphyrinate] with N-n-butyl-1,6,7,12-tetra(4-tert-butylphenoxyl)perylene-3,4-dicarboxylate anhydride-9,10-dicarboxylate imide (2) in the presence of imidazole in toluene afforded the novel perylene diimide-appended mixed (phthalocyaninato)(porphyrinato) europium(III) double-decker complex (5). Porphyrin–PDI dyad 4 was also obtained by similar method. The electronic absorption spectroscopic and electrochemical properties of PDI-appended double-decker 5 and the model compounds 2, 3, and 4 were studied, the results indicated that there was no considerable ground-state interaction between the double-decker unit and the PDI unit in 5. The fluorescence measurements revealed that the emission of PDI unit was effectively quenched by the double-decker…

A novel phthalocyanine–porphyrin–PDI array containing a sandwich-type mixed (phthalocyaninato)(porphyrinato) europium(III) double-decker core and a PDI modifier was designed and synthesized. The steady-state electronic absorption and electrochemical studies indicated that there was no ground-state interaction between the double-decker unit and the PDI unit. The fluorescence measurements revealed that the emission of PDI unit was remarkably quenched by the double-decker unit, suggesting considerable intramolecular interaction under excited state. Highlights: ► A PDI-appended mixed Eu(Pc)(Por) double-decker complex was synthesized. ► The electronic absorption and electrochemical properties were studied. Interaction between the double-decker unit and the PDI unit was not observed at ground state. ► The emission of PDI unit was quenched by the double-decker unit. Considerable intramolecular interaction exists at excited state.
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