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Dibenzo tetrathiafulvalene tetracarbonyl imide derivative and preparation method and uses thereof

A technology of dibenzotetrathiafulvalene tetracarbonyl diimide and benzotetrathiafulvalene tetracarbonyl diimide, which is applied in the field of organic semiconductor materials and can solve the problem of poor compound derivation ability and TTF derivatives Lack of synthetic routes, difficult synthesis and other problems, to achieve the effects of low synthesis cost, good application prospects, and high mobility

Inactive Publication Date: 2008-04-16
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, most of the TTF derivatives used as field effect transistors lack a universal synthetic route, the derivatization ability of the compound is poor, and the synthesis is difficult

Method used

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  • Dibenzo tetrathiafulvalene tetracarbonyl imide derivative and preparation method and uses thereof
  • Dibenzo tetrathiafulvalene tetracarbonyl imide derivative and preparation method and uses thereof
  • Dibenzo tetrathiafulvalene tetracarbonyl imide derivative and preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1, N, N'-dibutyl-dibenzotetrathiafulvalene-2,3,6,7-tetracarbonyl imide (compound 1)

[0038] Under the protection of nitrogen, 6.0g (28mmol) of 4,5-dichlorophthalic anhydride, 4.1g (56mmol) of n-butylamine, and 100mL of propionic acid were added to a 250ml three-neck flask, and the mixture was refluxed at 140°C for 3 hours. The reaction solution was cooled to room temperature, the solvent was rotated off under reduced pressure, and recrystallized in methanol to obtain 6.5 g of a white crystalline solid (Compound 3), with a yield of 85.5%.

[0039] Mass spectrum: [MS (EI)] m / z: 271 (M + ).

[0040] Elemental analysis: Molecular formula: C 12 h 11 Cl 2 NO 2 ;Theoretical value: C, 52.96H; 4.07; N, 5.15;

[0041] Found: C, 52.97; H, 4.13; N, 5.13.

[0042] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3)δ (ppm): 0.92-0.97 (t, J = 7.30Hz, 3H), 1.31-1.39 (m, 2H), 1.65 (m, 2H), 3.65-3.70 (t, J = 7.23Hz, 2H), 7.91(s, 2H).

[0043] NMR carbon spectrum: 13 C-NMR (75MH...

Embodiment 2

[0061] Example 2, N, N'-dihexyl-dibenzotetrathiafulvalene-2,3,6,7-tetracarbonyl imide (compound 2)

[0062] Compound 4 is the same as the synthesis of compound 3 in Example 1, using n-hexylamine as the amine (octylamine or n-dodecylamine, etc. can also be used): the yield is 86.5%.

[0063] Mass Spectrum: [MS(EI)] m / z: 299 (M + ).

[0064] Elemental analysis: Molecular formula: C 14 h 15 Cl 2 NO 2 ;Theoretical value: C, 56.02; H, 5.04; N, 4.67;

[0065] Found: C, 56.04; H, 5.08; N, 4.63.

[0066] H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 0.85-0.89 (t, J = 6.41Hz, 3H), 1.30 (s, 6H), 1.65 (m, 2H), 3.64-3.68 (t, J = 7.26Hz, 2H), 7.90 ( s, 2H).

[0067] NMR carbon spectrum: 3 C-NMR (75MHz, CDCl 3 )δ (ppm): 12.8, 21.3, 25.3, 27.3, 30.2, 37.4, 124.1, 130.2, 137.6, 165.2 (CO).

[0068] Synthesis of compound 6 with compound 5: the yield is 61%.

[0069] Mass spectrum: [MS(EI)] m / z: 475 (M + ).

[0070] Elemental analysis: Molecular formula: C 28 h 29 NO 2 S ...

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Abstract

A derivative of dibenzo-tetrathiafulvalene-tetrahydroxy-succinimide is provided, which has the structure shown by the right formula, in which R represents an alkyl. The preparation method includes the following procedures that: A) a mixture of dichlorophthalic anhydride and amine with the molecular ratio of 1: 1.5-3 undergoes circumfluence in propionic acid under 140 DEG C to 160 DEG C for 2-4 hours, B) the products obtained in procedure A is mixed with benzyl mercaptan with the molecular ratio of 1:2-3 and then undergoes calefaction in dimethylacetamide under the condition with excessive dosage of K2CO3 under 60 DEG C to 80 DEG C and, C) the product obtained in procedure B is kept in dry toluene with excessive dosage of AlCl3 to undergo debenzylation, and then reacts with carbonyldiimidazole under 70 DEG C to 90 DEG C for 2-5 hours, wherein the molecular ratio between 4,5-[(diphenylmethyl)thio substituted]- phthalimide and the carbonyldiimidazole is 1:1-3 and, D) the product obtained in procedure C undergoes circumfluence in a mixture of toluene / triethyl phosphate, the molecular ratio of which is 2-3 / 1 to carry out the auto-coupling reaction for 2-5 hours, the product of which is cooled down and filtrated to obtain the target product.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to a dibenzotetrathiafulvalene tetracarbonyl imide derivative. [0002] The present invention also relates to a preparation method of the above-mentioned organic semiconductor material. [0003] The present invention also relates to the application of the above-mentioned organic semiconductor material in an organic field effect transistor. Background technique [0004] Since the first organic field-effect transistor (OFET) was reported in 1986 (Tsumura, A.; Koezuka, H.; Ando, ​​T. Appl. Phys. Lett, 1986, 49, 1210.), OFET has made great progress develop. It has many unique properties, so more and more people pay attention to it. The advantages of organic field-effect transistors are: simple preparation process, low cost, light weight and good flexibility. It can be used in smart cards, electronic trademarks, electronic paper, memory, sensors and active matrix displays. It is an...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D495/04
Inventor 刘云圻高希珂王鹰邱文丰于贵朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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