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Paper | Special issue | Vol 84, No. 2, 2012, pp.815-828
Published online, 15th September, 2011
DOI: 10.3987/COM-11-S(P)59
Synthesis and Properties of Unsymmetrical N,N’-Dialkylterrylenebis(dicarboximide) Derivatives and Their Related Derivatives

Yukinori Nagao,* Tomohiro Iwano, Maki Hirano, Koji Arimitsu, and Kozo Kozawa

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

Terrylene derivatives have optical absorptions in the longer wavelength region than the perylene dyes and an unsymmetrical terrylene derivatives are expected to have an improved orientation and solubility. Unsymmetrical terrylenebis(dicarboximide) derivatives and their related dicarboximide derivatives were prepared, and the absorption or emission of light in a solution or solid film and their semiconductor-character for Schottky devices or dye sensitized solar cell devices were investigated. In solution, unsymmetrical and symmetrical terrylene derivatives showed the same absorption or emission spectra and have absorption or emission peaks in the longer wavelength region than that of the perylenedicarboximide derivatives. In a solid, the terrylene derivatives showed broad absorption peaks in the wavelength region shorter than that in solution. The terrylene derivatives behaved as an n-type semiconductor for a Schottky device and their conversion efficiencies were equivalent value to that of the typical semiconductor phthalocyanine (H2Pc). Perylenedicarboximide derivatives having a naphthalic anhydride moiety behave as a sensitizing dye for a dye sensitized solar cell.