A twin-TCNQ-type acceptor. Synthesis of 11,11,12,12,13,13,14,14-octacyano-1,4:5,8-anthradiquinotetramethane and structures of the tetraethylammonium salts of its mono- and dianion.
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概要
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The title compound (OCNAQ) was synthesized. Treatment of 1,2,3,4,5,6,7,8-octahydroanthracene with <I>N</I>-bromosuccinimide (NBS) under irradiation using a 100-W light bulb in refluxing CCl<SUB>4</SUB> followed by dicyanomethylation with excess of NaCH(CN)<SUB>2</SUB> in Me<SUB>2</SUB>SO gave an isomeric mixture of 1,4,5,8-tetrakis(dicyanomethyl) derivatives. The mixture was subjected by repetition of the successive bromination-dehydrobromination procedure giving OCNAQ in 20% overall yield. The cyclic voltammogram of OCNAQ exhibits four redox waves (<I>E</I><SUB>1⁄2</SUB><SUP>1</SUP> 0.26, <I>E</I><SUB>1⁄2</SUB><SUP>2</SUP> 0.05, <I>E</I><SUB>1⁄2</SUB><SUP>3</SUP> −0.44, and <I>E</I><SUB>1⁄2</SUB><SUP>4</SUP> −0.53 V vs. SCE in MeCN), indicating that OCNAQ is a stronger acceptor than tetracyanoquinodimethane (TCNQ, <I>E</I><SUB>1⁄2</SUB><SUP>1</SUP> 0.17 V vs. SCE). Both 1:1 and 2:1 salts, (Et<SUB>4</SUB>N)(OCNAQ) and (Et<SUB>4</SUB>N)<SUB>2</SUB>(OCNAQ), were obtained from reactions of Et<SUB>4</SUB>NI with potassium and lithium salts of OCNAQ, respectively. The X-ray crystal analyses of these salts indicate that the TCNQ moieties are boat-shaped bent to opposite directions. With the 1:1 salt, which behaves as a semiconductor (4×10<SUP>−4</SUP>Ω<SUP>−1</SUP> cm<SUP>−1</SUP> at room temperature, <I>E</I><SUB>a</SUB> 0.22 eV), the OCNAQ molecules are arrayed in the segregated stacking mode, while the 2:1 salt (10<SUP>−4</SUP>Ω<SUP>−1</SUP> cm<SUP>−1</SUP>) has no columnar structure of the OCNAQ molecules.
- 公益社団法人 日本化学会の論文
著者
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Maruyama Yusei
Institute for Molecular Science
-
Inabe Tamotsu
Institute for Molecular Science
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Honda Kazumasa
National Chemical Laboratory for Industry
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Watanabe Tokuko
Laboratory Of Chemistry The Tokyo University Of Marine Science
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Sugawara Tadashi
Department Of Basic Science Graduate School Of Arts & Sciences The University Of Tokyo
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Mitsuhashi Tsutomu
Department of Chemistry, Faculty of Science, The University of Tokyo
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Goto Midori
National Chemical Laboratory for Industry
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Sugawara Tadashi
Department of Pure and Applied Sciences, College of Arts and Sciences, The University of Tokyo
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