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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Published inTetrahedron letters Vol. 55; no. 33; pp. 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 Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.08.2014
Elsevier
Subjects
Band gap control
Chemistry
Chemistry, Organic
Fluorinated derivative
Organic photovoltaic cell
Physical Sciences
Science & Technology
Subnaphthalocyanine
Organic photovoltaic cell
Fluorinated derivative
PNABFQQRTHVWSZ-UHFFFAOYSA-N
Band gap control
Subnaphthalocyanine
BORON-SUBPHTHALOCYANINE
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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