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N-type neutral double-free-radical conductive compound as well as preparation method and application thereof

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: 2020-08-18
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 double-free-radical conductive compound as well as preparation method and application thereof
  • N-type neutral double-free-radical conductive compound as well as preparation method and application thereof
  • N-type neutral double-free-radical conductive compound as well as preparation method and application thereof

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 the compound 2DQQT-S in the above examples were respectively dissolved in dichloromethane (about 0.00001mol / L) and spin-coated into a thin film, 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 film has a significant red shift compared with that of the solution, and a shoulder peak is 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 pr...

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Abstract

The invention belongs to the technical field of organic conductors, and particularly relates to an N-type neutral double-free-radical conductive compound as well as a preparation method and application thereof. The compound shown in the formula (I) has a rigid large pi-conjugated plane and strong double-free-radical characteristics, and has excellent conductivity. Moreover, the compound as shown in the formula (I) prepared by the invention has the characteristic of easiness in functionalization, and the effective regulation and control of the self-doping degree can be realized by virtue of thearomaticity of a heterocyclic ring. In addition, the preparation method of the compound shown in the formula (I) is simple, high in product yield and suitable for industrial large-scale production. The structure of the compound shown in the formula (I) is shown in the specification.

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 Applications(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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