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DCNQI Anion‐Radical Salts with Bisammonium Cations
Author(s) -
Hünig Siegfried,
Metzenthin Tobias,
Peters Karl,
von Schütz JostUlrich,
von Schnering Hans Georg
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199808)1998:8<1653::aid-ejoc1653>3.0.co;2-r
Subject(s) - dication , chemistry , stacking , crystallography , ion , stoichiometry , molecule , crystallization , radical ion , crystal structure , zigzag , inorganic chemistry , organic chemistry , geometry , mathematics
Radical‐anion salts have been prepared by electro‐crystallization from seven 2,3‐ and 2,5‐disubstituted DCNQIs and the quaternary dications (AMM 2+ ) HMED, DMBP, EBP, and EBBT. The black compounds adopt the stoichiometry DCNQI/dication = 3:1. The crystal‐structure analysis of two of these radical salts reveal skewed (zigzag, trimerized) stacks of DCNQI molecules separated by sheets of dications. Specific interactions between DCNQI anions and dications are absent. The effect on the stacking of the DCNQI units of the two positive charges in the dications which are held apart at a defined separation is discussed. The salts are shown to be semiconductors with powder conductivities of 10 −2 to 10 −5 S cm −1 .