Structural characterization and properties of a new tetrathiafulvalene‐based cage molecule derived from an azacrown
Source abstract
Abstract
Communication: A cage molecule combining a precursor of the electroactive tetrathiafulvalene (TTF) unit with a macrocycle capable of complexing transition metals (see Figure) is reported. The preparation of this compound and the TTF‐based compound whose cavity is too small for complexing the metal are reported. magnified image
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Research context
OpenAlex topics: Organic and Molecular Conductors Research · Magnetism in coordination complexes · Molecular Junctions and Nanostructures
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References (16)
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1. 10.1039/p1990000017510.1039/p19900000175 ↗
2. Girmay B. · J. Chem. Soc., Chem. Commun. · 1989 · 1406
3. 10.1002/anie.19881377110.1002/anie.198813771 ↗
4. 10.1002/ange.1988100103710.1002/ange.19881001037 ↗
5. 10.1002/anie.19901450110.1002/anie.199014501 ↗
6. 10.1002/ange.1990102123710.1002/ange.19901021237 ↗
7. 10.1055/s-1987-2809510.1055/s-1987-28095 ↗
8. Physical data:1: Yield: 31 %. Elemental analysis: Found: C:39.34 H:4.66 N:5.55 S:50.06. Calc.: C:38.55 H:4.42 N:5.62 S:51.41; Color: light orange; Recrystallized from: chloroform/methanol; Mp.: 248–49°C.1H‐NMR (250 MHz CDCl3): δ = 2.25 (s CH3N) 2.31 (m CH2N) 2.67 (m CH2s CH2N) 3.27 (m CH2S). IR(KBr): 1044 cm−1(C=S). EIMS: 498 (81 %) 500 (32 %). UV (CHCL3): 344 nm/4.07 265 nm/ 4.26 241 nm/4.17. 2: Yield: 20%. Elemental analysis: Found: C:34.73 H:4.13 N:5.03 S:56.41. Calc.: C:34.13 H:3.94 N:4.98 S:56.95; Color: yellow feathers. Recrystallized from: toluene/methanol. Mp.: 160–62°C;1H‐NMR (250 MHz CDCl3): δ = 2.31 (s CH3N) 2.77 (t CH2N) 3.07 (t CH2S). IR (KBr): 1065 cm−1(C=S). PDMS: 563.5 m/z (molecular weight calculated: 563.0). UV (CHCl3): 386 nm/4.10 276 nm/3.89 241 nm/3.89. 3: Yield: 1 %. Peak matching: Found: 280.9495. Calc.: 280.9483. Color: yellow feathers. Recrystallized from: chloroform/petroleum ether (Bp. 65–70°C). Mp.: 106–8°C;1H‐NMR (250 MHz CDCL3): δ = 2.28 (s CH3N) 2.81 (m CH2N) 2.90 (m CH2S). IR (KBr): 1051 cm−1(C=S). PDMS: 282.1 m/z (calculated: 281.5). UV (CHCL3): 376 nm/4.08 269 nm/ 3.56 241 nm/3.82. 4: Yield: 9%. Elemental analysis: Found: C:34.33 H:3.96 N:4.91; S:56.16. Calc.: C:34.13 H:3.94 N:4.98 S:56.95; Color: yellow feathers. Recrystallized from: ethylacetate/methanol; Mp.: 113–14°C;1H‐NMR (250 MHz CDCL3): δ = 2.32 (s CH3N) 2.75 (t CH2N) 3.04 (t CH2S). IR (KBr): 1066 cm−1(C=S). PDMS: 845.8 m/z (calculated: 844.5). UV (CHCL3): 384 nm/4.37 275 nm/4.16 240 nm/4.25.
9. Plasma desorption spectra were recorded on a BioIon 10 K time‐of‐flight mass spectrometer (applied Biosystems Uppsala Sweden) for 5 × 105fission events. The samples were applied from a trifluoroacetic acid solution on a slowly spinning nitrocellulose‐covered target. The spectra were calibrated using the peaks form H⊕ and NO⊖. Due to low resolution of the instrument the measured molecular weight is the isotopically averaged.
10. 10.1021/jo00335a03210.1021/jo00335a032 ↗
11. Dimer (2): K⊕‐template (yield 2%) Rb⊕‐template (yield 7%) Cs⊕‐template (yield 20%). Monomer (3): K⊕‐template (yield 0%) Rb⊕‐template (yield 1 %) Cs⊕‐template (yield 1 %). Trimer (4): K⊖‐template (yield 0%) Rb⊖‐template (yield 2%) Cs⊕‐template (yield 9%).
12. (a) Crystal data for 1: Mr= 498.9 monoclinic space group P21/c at 122 k a = 9.644(3) b = 15.537(6) c = 14.287(2) Å. β = 91.23°. V = 2116(2) Å3. dcal= 1.566 gcm−3. Z = 4. F(000) = 1040 μ(Mokα) = 8.17 cm−1λ = 0.71073 Å. 4224 independent reflections 3616 (I ≥ 2 σ(1)) used in refinement weights w = (σ(FS) + 9 × 10−4Å∣F∣2)−1(σcs(F) calculated from counting statistics R = 0.050 Rw= 0.077. Structure is disordered two different conformations (A and B) are found of the C23 C13 N2 C14 chain. The largest peak 1.0 e/Å3in final difference density map is found in region of this disordered chain.
13. (b) Further details of the crystal structure investigation are available on request from the Director of the Cambridge Crystallographic Data Centre University Chemical Laboratory Lensfield Road Cambridge CB2 1EW (UK) on quoting the full journal citation.
14. 10.1002/9780470166369.ch210.1002/9780470166369.ch2 ↗
15. 10.1021/ja00165a09310.1021/ja00165a093 ↗
16. Silver complex of compound 2 92 % yield orange crystals Mp. 170‐72°C (some decomposition observed at 130°C). The fast atom bombardment (FAB) mass spectrum obtained from a solution of the AgNO3complex with 2 in DMSO and glycerol showed a molecular ion peak at m/z 670.8 (M⊖). Isotopic pattern for the molecular formula (C16H22N2S10Ag) calc.: 73% (M⊕ – 2) 20% (M⊕ – 1) 100%(M⊕) 30% (M⊕ + 1) 40% (M⊕ + 2) 10% (M⊕ + 3) 7% (M⊕ + 4); Found: 70% (M⊖ – 2) 30% (M⊕–1) 100%(M⊕) 41% (M⊕+1) 44% M⊕ +2) 16% (M⊕ +3) 8 % (M⊕ + 4).