First stable tetracyanodiphenoquinodimethane with a completely planar geometry: Preparation, X-ray structure, and highly conductive complexes of bis[1,2,5]thiadliazolo-TCNDQ

被引:24
作者
Fukushima, T
Okazeri, N
Miyashi, T [1 ]
机构
[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan
[2] Grad Univ Adv Studies, Dept Struct Mol Sci, Okazaki, Aichi 4448585, Japan
[3] Inst Mol Sci, Okazaki, Aichi 4448585, Japan
[4] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan
关键词
electrical conductors; organic; quinoid compounds; thiadiazoles; X-ray crystal structures;
D O I
10.1016/S0040-4039(98)02557-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The titled tetracyanodiphenoquinodimethane (TCNDQ) derivative was newly designed and prepared as a novel component for highly conductive organic materials. Introduction of 1,2,5-thiadiazole rings into the TCNDQ skeleton leads to large stabilization in the neutral state. X-ray analysis bas:revealed their structural details which suggest that interatomic interactions (C-H ... N, S ... N) play an important role in determining the molecular and crystal structure. The novel electron acceptor shows strong electron affinity comparable with that of TCNQ, and gave highly conductive charge-transfer (CT) complexes and an anion radical salt. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1175 / 1178
页数:4
相关论文
共 18 条
[1]   PREPARATION AND OXIDATION OF THE BIS(TETRA-NORMAL-BUTYLAMMONIUM) SALT OF 2,2'-(2,7-PYRENEDIYL)BIS[PROPANEDINITRILE] DIANION [J].
ACTON, N ;
HOU, D ;
SCHWARZ, J ;
KATZ, TJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06) :1011-1018
[2]   CHEMISTRY OF ANIONS DERIVED FROM TETRACYANODIPHENOQUINODIMETHANE (TCNDQ) [J].
ADDISON, AW ;
DALAL, NS ;
HOYANO, Y ;
HUIZINGA, S ;
WEILER, L .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (24) :4191-4199
[3]  
AHARONSHALOM E, 1979, NOUV J CHIM, V3, P643
[4]  
BECHGAARD K, 1990, STRUCTURE PROPERTIES, P235
[5]   THE ROLE PLAYED BY C-H...O AND C-H...N INTERACTIONS IN DETERMINING MOLECULAR PACKING AND CONFORMATION [J].
BERKOVITCHYELLIN, Z ;
LEISEROWITZ, L .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1984, 40 (APR) :159-165
[6]  
COTTON FA, 1997, J CHEM SOC CHEM COMM, P1673
[7]   SUPRAMOLECULAR SYNTHONS IN CRYSTAL ENGINEERING - A NEW ORGANIC-SYNTHESIS [J].
DESIRAJU, GR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (21) :2311-2327
[8]   HOMOCOUPLING OF ARYL HALIDES USING NICKEL(II) COMPLEX AND ZINC IN THE PRESENCE OF ET4NI - AN EFFICIENT METHOD FOR THE SYNTHESIS OF BIARYLS AND BIPYRIDINES [J].
IYODA, M ;
OTSUKA, H ;
SATO, K ;
NISATO, N ;
ODA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (01) :80-87
[9]   SYNTHESIS OF 13,13,14,14-TETRACYANOPYRENO-2,7-QUINODIMETHANE, AN ELECTRON-ACCEPTOR FOR ORGANIC METALS [J].
MAXFIELD, M ;
WILLI, SM ;
COWAN, DO ;
BLOCH, AN ;
POEHLER, TO .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (20) :947-948
[10]   LARGE ELECTRON-ACCEPTORS FOR MOLECULAR-METALS - 13,13,14,14-TETRACYANO-4,5,9,10-TETRAHYDRO-2,7-PYRENOQUINODIMETHANE (TCNTP) AND ANIONS OF 13,13,14,14-TETRACYANO-2,7-PYRENOQUINODIMETHANE (TCNP) [J].
MAXFIELD, M ;
BLOCH, AN ;
COWAN, DO .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) :1789-1796