N-type neutral diradical conductive compound and its preparation method and application

A compound and selected technology, applied in the direction of organic chemistry, can solve the problem that quinone diradicals have not been considered

Active Publication Date: 2021-08-17
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally speaking, the vast majority of neutral single-component organic conductors are monoradical conductors and no N-type conductors have been reported, and quinone diradicals have hardly been considered as conductors.

Method used

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  • N-type neutral diradical conductive compound and its preparation method and application
  • N-type neutral diradical conductive compound and its preparation method and application
  • N-type neutral diradical conductive compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1: Preparation of 2DQQT-Se

[0074]

[0075] 1) Preparation of compound (III-1): Dissolve compound (IV-1) (100mg, 0.11mmol) and (V-1) (148mg, 0.264mmol) in dry toluene (2mL) and DMF (2mL) In the mixed solvent, add it to the pressure-resistant tube under inert conditions, and ventilate for 20 minutes to remove oxygen. Add tetrakis triphenylphosphine palladium [Pd (PPh 3 ) 4 ] (6.36 mg, 0.0055 mmol). Wherein compound (IV-1) and compound (V-1) and Pd(PPh 3 ) 4 The molar ratio is 1:2.4:0.05. Stir at 90°C for two days, cool to room temperature after the reaction, remove the solvent, and purify the crude product by silica gel column chromatography to obtain 134 mg of red solid compound (III-1), with a yield of 90% .

[0076] 2) Preparation of compound (II-1): Add compound (III-1) (134 mg, 0.099 mmol) into a single-necked bottle under light-shielded conditions. Chloroform (3 mL) and DMF (1 mL) were added to dissolve, and then NBS (39 mg, 0.219 mmol) was ad...

Embodiment 2

[0078] Embodiment 2: Preparation of 2DQQT-S

[0079]

[0080] Referring to the preparation method of Example 1, 2DQQT-S can be prepared with a yield of 50%. HRMS (MALDI-TOF) molecular formula: C 74 h 94 N 6 O 4 S 4 S 2 . [M+H] + Theoretical value: 1322.565533, measured value: 1322.564814.

Embodiment 3

[0081] Embodiment 3: performance test

[0082] The compound 2DQQT-Se and compound 2DQQT-S in the above examples were dissolved in dichloromethane (about 0.00001mol / L) and spin-coated into thin films, and tested at room temperature using a UV-visible spectrophotometer. See results figure 1 . It can be seen that the solutions of the two compounds both exhibit strong absorption in the near-infrared region. The absorption of the thin film is obviously red-shifted compared with that of the solution, and shoulder peaks are generated in the wavelength range of 1300-1500nm, resulting in a very narrow band gap. The surface molecules can generate quinone and aromatic resonances at room temperature, and self-doping, This point can be further proved by combining theoretical calculations, energy spectra and single crystal data. In addition, in the 2DQQT-Se film, there is a broad charge vibration peak absorption, which corresponds to its high doping degree, which also proves that the in...

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Abstract

The invention belongs to the technical field of organic conductors, and in particular relates to a class of N-type neutral diradical conductive compounds and a preparation method and application thereof. The compound of formula (I) prepared by the invention has a large rigid π-conjugated plane and strong double radical characteristics, and has excellent electrical conductivity. Moreover, the compound of formula (I) prepared by the present invention has the feature of being easy to be functionalized, and the degree of self-doping can be effectively regulated by virtue of the aromaticity of the heterocycle. In addition, the preparation method of the compound of formula (I) of the present invention is simple, the product yield is high, and it is suitable for large-scale industrial production. The structure of the compound of formula (I) is as follows:

Description

technical field [0001] The invention belongs to the technical field of organic conductors, and in particular relates to a class of N-type neutral diradical conductive compounds and a preparation method and application thereof. Background technique [0002] Conduction is one of the important characteristics of organic conjugated materials, and has broad prospects in the fields of organic spin devices, superconductors, and thermoelectric devices (R.C.Haddon.Nature.1975,256,394.X.Chi,M.E.Itkis,B.O.Patrick,T.M.Barclay , R.W. Reed, R.T. Oakley, A.W. Cordes, R.C. Haddon, J. Am. Chem. Soc. 1999, 121, 10395.). In recent years, neutral single-component organic conductors have received extensive attention, mainly due to their simple preparation and controllable properties (Y.Kobayashi, T.Terauchi, S.Sumi, Y.Matsushita, Nat.Mater.2017, 16, 109. Y. Joo, V. Agarkar, S.H. Sung, B.M. Savoie, B.W. Boudouris, Science. 2018, 359, 1391. A. Mailman, A.A. Leitch, W. Yong, E. Steven, S.M. Winter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 朱晓张袁达飞
Owner INST OF CHEM CHINESE ACAD OF SCI
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