Extended bis‐fused tetrathiafulvalenes incorporating a heteroaromatic π‐electron spacer
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Abstract
New π‐electron donors are being sought for the preparation of organic conductors. The first synthesis of bis‐fused π‐electron donors incorporating a heteroaromatic π‐electron spacer (see Figure) is reported. The electrochemical properties of 3a–c and 4a–c and the crystal structure of 3c are presented, the results for the TCNQ complexes 3a and 4a confirming that the fusion of two donor units is a suitable strategy for the development of highly conducting molecular complexes. magnified image
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Research context
OpenAlex topics: Organic and Molecular Conductors Research · Magnetism in coordination complexes · Perovskite Materials and Applications
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References (23)
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15. The aldehydes 6c and 7c were prepared by the procedure similar to 6b and 7b see Ref. 8
16. IR: (KBr) 1731 (C=O) 1712 (C=O) 1580 (C=C) cm−1;1H‐NMR (270 MHz 400 MHz CDCl3 25°C TMS): δ = 6.82 (s 2H) 6.74 (s 1H) 6.61 (s 1H) 3.89 (s 3H) 3.87 (s 3H) 3.86 (s 6H). 3c: dark red crystals
17. IR: (KBr) 1602 (C=C) 1525 (C=C) cm−1;1H‐NMR (270 MHz CS2‐[D6]benzene. 25°C TMS): δ = 6.29 (s 1H) 6.26 (s 1H) 6.21 (s 1H) 6.18 (s 1H) 6.09 d J(H H) = 3.5 Hz 1H) 6.07 (d J(H H) = 3.5 Hz 1H). 4b: dark brown powder
18. IR: (KBr) 1729 (C=O) 1582 (C=C) cm−1;1H‐NMR (270 MHz CS2‐[D6]benzene. 25°C TMS): δ = 6.24 (s 1H) 6.12 (s 1H) 6.07 (d J(H H) = 4.1 Hz 1H) 6.06 (d J(H H) = 4.1 Hz 1H) 3.66 (s 3H) 3.64 (s 3H) 3.63 (s 3H) 3.60 (s 3H). 4c: orange powder
19. IR: (KBr) 1600 (C=C) cm−1;1H‐NMR (400 MHz CDCl3 25°C TMS): δ = 6.43 (s 1H) 6.35 (s 1H) 6.21 (d J(H H) = 3.4 Hz 1H) 6.17 (d J(H H) = 3.4 Hz 1H) 2.47 (s 3H) 2.44 (s 3H) 2.432 (s 3H) 2.428 (s 3H).
20. Selected spectral data. 3a: orange powder; m. p. 173-174.5°C (dec.); IR: (KBr) 1570 (C=C) 1523 (C=C) cm−1;1H‐NMR (270 MHz CS2‐[D6]benzene 25°C TMS): δ = 6.65 (s 2H) 6.53 (s 2H) 6.20 (s 2H) 6.15 (s 1H) 6.14 (s 1H). 3b: dark brown powder; m.p. 213.5-215°C (dec.); IR: (KBr) 1731 (C=O) 1712 (C=O) 1580 (C=C) cm−1;1H‐NMR (270 MHz 400 MHz CDCl3 25°C TMS): δ = 6.82 (s 2H) 6.74 (s 1H) 6.61 (s 1H) 3.89 (s 3H) 3.87 (s 3H) 3.86 (s 6H). 3c: dark red crystals; m.p. 147-149°C (dec.): IR: (KBr) 1570 (C=C). 1555 (C=C) cm−1;1H‐NMR (270 MHz CS2‐[D6]benzene 25°C TMS): δ = 6.67 (d J(H H) = 3.8 Hz
21. (1H) 6.64 d J(H H) = 3.8 Hz 1H 6.56 (s 1H) 6.46 (s 1H) 2.39 (s 3H) 2.38 (s 3H) 2.37 (s 3H) 2.36 (s 3H). 4a: orange powder; m.p. 163.5-164°C (dec.); IR: (KBr) 1602 (C=C) 1525 (C=C) cm−1;1H‐NMR (270 MHz CS2‐[D6]benzene. 25°C TMS): δ = 6.29 (s 1H) 6.26 (s 1H) 6.21 (s 1H) 6.18 (s 1H) 6.09 d J(H H) = 3.5 Hz 1H) 6.07 (d J(H H) = 3.5 Hz 1H). 4b: dark brown powder; m.p. 193-194.5°C (dec.); IR: (KBr) 1729 (C=O) 1582 (C=C) cm−1;1H‐NMR (270 MHz CS2‐[D6]benzene. 25°C TMS): δ = 6.24 (s 1H) 6.12 (s 1H) 6.07 (d J(H H) = 4.1 Hz 1H) 6.06 (d J(H H) = 4.1 Hz 1H) 3.66 (s 3H) 3.64 (s 3H) 3.63 (s 3H) 3.60 (s 3H). 4c: orange powder; m.p. 135‐136°C (dec.); IR: (KBr) 1600 (C=C) cm−1;1H‐NMR (400 MHz CDCl3 25°C TMS): δ = 6.43 (s 1H) 6.35 (s 1H) 6.21 (d J(H H) = 3.4 Hz 1H) 6.17 (d J(H H) = 3.4 Hz 1H) 2.47 (s 3H) 2.44 (s 3H) 2.432 (s 3H) 2.428 (s 3H).
22. Crystal data of 3c: monoclinic space group C2/c a = 46.250(8) b = 5.16(1) c = 27.023(8) Å β = 123.82(1)° V = 5359(12) Å3 Z = 8 ρcalcd= 1.668 g cm−3. The data were collected on a Rigaku AFC‐7R diffractometer with graphite monochromatized MoKα radiation. Anisotropic thermal parameters were adopted for all non‐hydrogen atoms. The finalR(Rw) value is 0.073 (0.067) for 1080 independent reflections (∣I∣ > 3σ(I)). Further details of the crystal structure investigation may be obtained from the Director of the Cambridge Crystallographic Data Centre 12 Union Road Cambridge CB2 1EZ (UK) on quoting the full journal citation.
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