Synthesis and properties of novel fluorinated subnaphthalocyanines for organic photovoltaic cells

Novel fluorinated subnaphthalocyanine derivatives were newly designed and synthesized as donor materials for low molecular organic photovoltaic cells using fullerene as an acceptor. They were designed to have the low-lying HOMO energy levels for improvement of open circuit voltage without any expens...

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Bibliographic Details
Published in:Tetrahedron letters 2014-08, Vol.55 (33), p.4564-4567
Main Authors: Takao, Yuko, Masuoka, Tomoaki, Yamamoto, Koji, Mizutani, Tadashi, Matsumoto, Fukashi, Moriwaki, Kazuyuki, Hida, Koichi, Iwai, Toshiyuki, Ito, Takatoshi, Mizuno, Takumi, Ohno, Toshinobu
Format: Article
Language:English
Subjects:
Band gap control
Fluorinated derivative
Organic photovoltaic cell
Subnaphthalocyanine
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Summary:Novel fluorinated subnaphthalocyanine derivatives were newly designed and synthesized as donor materials for low molecular organic photovoltaic cells using fullerene as an acceptor. They were designed to have the low-lying HOMO energy levels for improvement of open circuit voltage without any expense of short-circuit current density. The HOMO/LUMO energy levels of hexafluoro-, heptafluoro-, dodecafluoro-, tridecafluoro- and the parent subnaphthalocyanine estimated based on the photoelectron spectroscopy were −5.69/−3.93, −5.67/−3.90, −5.96/−4.19, −5.92/−4.11 and −5.30/−3.58eV, respectively, showing that frontier orbital energy levels can be effectively tuned by fluorination.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.06.069