Journal of the Chemical Society. Perkin transactions II p. 313 - 319 (1993)
Update date:2022-08-18
Topics:
Batsanov, Andrei S.
Bryce, Martin R.
Davies, Stephen R.
Howard, Judith A. K.
Whitehead, Roger
Tanner, Brian K
The reaction of tetramethyltetrathiafuvalene (TMTTF, 7) with 2-dicyanomethyleneindane-1,3-dione (DCID, 1) leads to isomerisation of DCID to 2,3-dicyanonaphthoquinone (DNCQ, 3) to yield the charge-transfer complex <(TMTTF)3>2.+-(DCNQ.-)2, 8.The X-ray crystal structure of complex 8 reveals stacks of TMTTF molecules along the x direction in the sequence A..B..A..A..B..A..etc.The A..A and A..B interplanar separation distances are 3.51 Angstroem and 3.44 Angstroem, respectively.The DCNQ radical anions form dimers, with a remarkably short interplanar separation of 3.02 Angstroem, which are orthogonal to the TMTTF stacks.The complex is diamagnetic.Other ?-acceptor molecules containing the dicyanomethylene group, viz. compounds 2 and 10 -12, have been prepared and their redox properties studied by cyclic voltammetry.Compound 2 rearranges to compound 4 on complexation with TTF 6.DCID derivatives 1 and 2 react with a range of amines, by displacement of one cyano group, to yield enamines 15-19; the amphiphilic compound 18 forms Langmuir-Blodgett films which exhibit weak second harmonic generation.
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