3 years ago

Multinuclear Phthalocyanine-Fused Molecular Nanoarrays: Synthesis, Spectroscopy, and Semiconducting Property

Multinuclear Phthalocyanine-Fused Molecular Nanoarrays: Synthesis, Spectroscopy, and Semiconducting Property
Zheng Xue, Hong Shang, Kang Wang, Huibiao Liu, Jianzhuang Jiang
The post-cyclization strategy rather than the conventional ante-cyclotetramerization method was employed for the synthesis of multinuclear phthalocyanine-fused molecular nanoarrays. Reaction of 2,3,9,10,16,17-hexakis(2,6-dimethylphenoxy)-23,24-diaminophthalocyaninato zinc(II) with 2,7-di-tert-butylpyrene-4,5-dione, 2,7-di-tert-butylpyrene-4,5,9,10-tetraone, and hexaketocyclohexane in refluxing acetic acid afforded the corresponding mono-, bi-, and trinuclear phthalocyanine-fused zinc complexes (Pz-pyrene){Zn[Pc(OC8H9)6]} (1), (Pz2-pyrene){Zn[Pc(OC8H9)6]}2 (2), {(HAT){Zn[Pc(OC8H9)6]}3} (3) in 46, 13, and 25 % yield, respectively, which extend the scope of multinuclear phthalocyanine-fused nanoarrays with different molecular skeletons. The self-assembly behavior of trinuclear phthalocyanine 3 in THF/CH3CN was investigated by electronic absorption spectroscopy and SEM, and the fabricated nanorods showed interesting semiconducting properties, which suggest good application potential of these multinuclear phthalocyanine-fused molecular nanoarrays. Trinuclear nanoarray: Conjugated multinuclear phthalocyanine molecular arrays with good semiconducting properties were synthesized by a post-cyclization strategy based on Schiff-base chemistry and characterized. The trinuclear phthalocyanine self-assembles into nanorods that show interesting semiconducting properties (see figure).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700291

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