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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 8
BKCSDE 32(8)
August 20, 2011 

Synthesis and Characterization of Bis-Thienyl-9,10-anthracenes Containing Electron Withdrawing 2-Cyanoacrylic Acid or 2-Methylenemalononitrile Group
Yuan Wang, Qu Feng Yu, Hea Jung Park, Suk Hwa Ryu, Jung Hei Choi, Ung Chan Yoon*,
Bis-thienylanthracene derivatives, 2-Malononitrile, 2-Cyanoacrylic acid, OPVs, DSSCs.
A series of new bis-thienylanthracene derivatives D1 ~ D5 containing 9,10-antharcene moiety in the center and 2-methylenemalonotitrile or 2-cyanoacrylic acid functional group on the terminal thiophenes were synthesized and characterized by 1H-NMR and high-resolution mass spectroscopy. Their optical, electrochemical, and thermal properties were measured. They have absorption λmax in the range of 437 ~ 480 nm and εmax of 7.4 × 103 ~ 2.0 × 104 M−1cm−1. The substitution of 2-cyanoacrylic acid group allows greater value of εmax than that of 2-methylenemalonotitrile. TGA curves showed that D4 and D5 which have 2-cyanoacrylic acid functional group on the terminal thiophene(s) exhibit good thermal stability and D4 was thermally stable up to 400 oC. Their optical properties and LUMO energy levels measured suggest that they can serve as potential candidates for electron donor materials of organic photovoltaic cells (OPVs) or D4 and D5 which contain 2-cyanoacrylic acid group can be used as organic dyes of dye-sensitized solar cells (DSSCs).
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