Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

Autor:	Yoshiro Yamashita, Tsutomu Miyashi, Yoshiaki Tsubata, Takanori Suzuki
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Nitrile Bicyclic molecule Radical Organic Chemistry Inorganic chemistry Salt (chemistry) Reaction intermediate Electron acceptor Redox Crystallography chemistry.chemical_compound chemistry Diamine
Zdroj:	The Journal of Organic Chemistry. 57:6749-6755
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00051a015
Popis:	Pyrazino-TCNQ (1a) prepared from 5, 8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo- 1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of 1a. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-[pi]-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 [times] 10[sup [minus]5] S cm[sup [minus]1]. 29 refs., 4 figs., 2 tabs.
Databáze:	OpenAIRE
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