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Multinuclear Phthalocyanine‐Fused Molecular Nanoarrays: Synthesis, Spectroscopy, and Semiconducting Property
Author(s) -
Shang Hong,
Xue Zheng,
Wang Kang,
Liu Huibiao,
Jiang Jianzhuang
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700291
Subject(s) - phthalocyanine , zinc , pyrene , nanorod , chemistry , yield (engineering) , spectroscopy , absorption (acoustics) , absorption spectroscopy , photochemistry , quantum yield , materials science , polymer chemistry , organic chemistry , nanotechnology , fluorescence , physics , quantum mechanics , metallurgy , composite material
Abstract 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(OC 8 H 9 ) 6 ]} ( 1 ), (Pz 2 ‐pyrene){Zn[Pc(OC 8 H 9 ) 6 ]} 2 ( 2 ), {(HAT){Zn[Pc(OC 8 H 9 ) 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/CH 3 CN 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.