Molecular and Crystal Structures of 2-Dicyanomethylene-1,1,3,4,5,5-Hexacyanopentenediide (DHCP) and its Tetrathiafulvalene (TTF) Complex

References

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• IR absorption patterns were compared with that reported in ref. 7 which had not given R4N+ bands. R = Me; The red crystals of R = Me melted at 214–216°C (IR (KBr) 2190 cm−1 (s), 1460(m), 1290(w), 1241(w)). The orange yellow crystals of R = Pr melted at 278°C (dec.) (IR (KBr) 2191 cm−1 (s), 1450 (m, shoulder), 1290(w), 1241(w))
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• The red crystals of R = Et melted at 209–213°C (lit. 205–211°C) and showed the following spectral data [in brackets the reported values are indicated]. IR (KBr) 2190(s), 1454 (s), 1299(w), 1240(w) [2193(s), 1453(s), 1297(w), 1239(w)], UV-Vis (in CH3CN) 329 nm (ε = 20230), 420 (20290) [328 (20100), 420 (20100)]
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• For (Me4N)2(C14N8); triclinic, P1, a ≈ 16.967(2) Å, b = 11.6810(8), c = 6.5556(9), α = 103.583(8)°, β = 96.11(1), γ = 90.968(8), V = 1254.6(2) Å3, data were collected at room temperature, Z = 2, R = 0.0787. For (Et4N)2(C14N8); triclinic, P1, a = 12.319(8) Å, b = 13.42(1), c = 11.845(9), α = 65.51(4)°, β = 64.78(5), γ = 78.95(6), V = 1612(2) Å3, data were collected at room temperature, Z = 2, R = 0.1354
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• Measured in 0.1 M (Bu4N)BF4 solution in CH3CN vs. SCE at 24°C and the scan rate of 0.2 V/sec.; under the same condition, TCNQ shows reversible redox peaks at −0.29 and 0.26 V for the oxidation processes of TCNQ2− → TCNQ− and TCNQ− → TCNQ, respectively
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• The donor molecules, which afforded the conductive salts were bis(ethylenedithio)-TTF (ET) (room temperature conductivity [sgrave]rt = 101 – 102 Scm−1), bis(ethylenedioxy)-TTF (BO) ([sgrave]rt = 102), bis(methylenedithio)-TTF ([sgrave]rt = 0.5), 3,4-ethylenedithio-TTF ([sgrave]rt = 102), bis(vinylenedithio)-TTF ([sgrave]rt = 102), and bis[oxybis(methylenethio)]-TTF ([sgrave]rt = 1)
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• (TTF)2(C14N8)(CH3CN); triclinic, P1, a = 8.917(1) Å, b = 21.891(3), c = 8.319(1), α = 91.64(1)°, β = 101.13(2), γ = 91.74(2), V = 1592(1) Å3, data were collected at room temperature, Z = 2, R = 0.0525
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• Also, the positional parameters of C5 atom may be split into two positions, though the differential synthesis afforded no peaks around C5
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