Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials

Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthal...

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Bibliographic Details
Published in:Tetrahedron 2016-08, Vol.72 (32), p.4918-4924
Main Authors: Yamamoto, Koji, Takagi, Akuto, Hada, Miyako, Taniwaki, Ryosuke, Mizutani, Tadashi, Kimura, Yoshifumi, Takao, Yuko, Moriwaki, Kazuyuki, Matsumoto, Fukashi, Ito, Takatoshi, Iwai, Toshiyuki, Hida, Koichi, Mizuno, Takumi, Ohno, Toshinobu
Format: Article
Language:English
Subjects:
Absorption spectroscopy
Dipole moment
Electronics
Fluorescence
Halogen
HOMO
LUMO
Molecular orbitals
Optical property
Optoelectronics
Parents
Solubility
Subnaphthalocyanine
Tetrahedrons
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Summary:Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthalocyanine by 0.13–0.39 eV. The optical band gap decreased in the order: hexafluoro->hexachloro->unsubstituted>hexaiodo-subnaphthalocyanine. Fluorescence quantum yield of hexaiodosubnaphthalocyanine was 0.05, significantly lower than those of the parent, hexafluoro- and hexachloro-subnaphthalocyanines whose quantum yields ranged from 0.2 to 0.22, indicating that the heavy atom effects of iodine work effectively. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.06.064