Indole diketone small molecule as well as preparation method and application thereof

A technology of indole dione, small molecule compound, applied in semiconductor/solid state device manufacturing, organic chemistry, electric solid device and other directions, can solve the problems of batch limitation, complex polymer synthesis, etc., achieve structure determination, synthesis method Simple, high product purity

Pending Publication Date: 2022-06-28
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, polymer semiconductors have been widely studied, b

Method used

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  • Indole diketone small molecule as well as preparation method and application thereof
  • Indole diketone small molecule as well as preparation method and application thereof
  • Indole diketone small molecule as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1 Synthesis of Indoledione Small Molecular Compounds of General Formula (I) [Compound (1)]

[0072] According to the following reaction formula, 30.0 mg of compound 1 (1 equiv.) and 8.2 mg of malononitrile (2.5 equiv.) were added to a side-necked flask, and nitrogen was pumped for three times. After the reaction was carried out for 2 h, the solvent in the system was evaporated by rotary evaporation, and the compound (1) was obtained by purification through a silica gel chromatography column (eluent is dichloromethane).

[0073] Compound (1) 1 H NMR and mass spectra, see figure 1 , Image 6 , and the NMR data are as follows:

[0074] 1 H NMR (400MHz, CDCl 3 ,300K),δ(ppm):8.25(d,2H),7.92(d,2H),4.24(t,4H),1.82(m,4H),1.23-1.50(m,40H),0.90(t, 6H).

[0075]

[0076] Wherein, compound 1 was prepared by the method described in the existing literature [Onwubiko A, Yue W, Jellett C, et al. Fusedelectron deficient semiconducting polymers for air stable electron t...

Embodiment 2

[0077] Example 2 Synthesis of Indoledione Small Molecular Compounds of General Formula (I) [Compound (2)]

[0078] According to the following reaction formula, 30.0 mg of compound 2 (1 equiv.), 20.1 mg of 3-ethyl-2-thio-4-thiazolidinedione (2.5 equiv.) were added to a microwave tube, followed by 3 drops of triethylamine and 5 mL of ultra-dry chloroform was reacted at 60° C. for 1 h, the solvent in the system was evaporated by rotary evaporation, and the compound (2) was obtained by purification through a silica gel column (eluent: dichloromethane / methanol=100 / 2). Compound (2) 1 H NMR and mass spectra, see figure 2 , Figure 7 , and the NMR data are as follows:

[0079] 1 H NMR (400MHz, CDCl 3 ,300K),δ(ppm):9.09(d,2H),8.09(d,2H),4.57(t,4H),4.28(q,4H),3.94(t,4H),3.47-3.74(m, 24H), 3.37(s, 6H), 1.37(t, 6H).

[0080]

[0081] Among them, compound 2 was prepared by the method described in the existing literature (N-type Rigid Semiconducting Polymers Bearing Oligo (Ethyle...

Embodiment 3

[0082] Example 3 Synthesis of Indoledione Small Molecular Compounds of General Formula (I) [Compound (3)]

[0083] According to the following reaction formula, 30.0 mg of compound 2 (1 equivalent, the preparation method was the same as that of Example 2), 24.0 mg of 2-(3-ethyl-4-oxothiazolidine-2-ylidene)malononitrile (2.5 equivalents) ) into a microwave tube, then add 3 drops of triethylamine and 5 mL of ultra-dry chloroform, react at 60 °C for 1 h, evaporate the solvent in the system by rotary evaporation, and pass through a silica gel chromatography column (eluent is dichloromethane / methanol= 100 / 2) was purified to obtain compound (3). Compound (3) 1 H NMR chart see image 3 , and the NMR data are as follows:

[0084] 1 H NMR (400MHz, CDCl 3 ,300K),δ(ppm):8.95(d,2H),8.10(d,2H),4.53(t,4H),4.40(q,4H),3.91(t,4H),3.45-3.68(m, 24H), 3.34(s, 6H), 1.37(t, 6H).

[0085]

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Abstract

The invention belongs to the technical field of organic semiconductor materials, and particularly relates to an indole diketone small molecule and a preparation method and application thereof, a novel indole diketone small molecule compound is synthesized through a very simple method, the synthesis method is simple and convenient, and the yield is high. The obtained compound has better dissolving property and absorption energy level, and compared with other polymer materials, the small molecule compound has the advantages of definite structure, high product purity and higher yield. The small molecular compound obtained by the simple method has a good planar rigid structure and good accumulation, is beneficial to transmission of electrons among molecules, and has potential application prospects in the fields of visible light, organic electrochemical transistors (OECT), organic thermoelectricity (OTE), organic field effect transistors and the like at the maximum absorption wavelength.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and particularly relates to an indole dione small molecule and a preparation method and application thereof. Background technique [0002] Indole dione derivatives are a very important class of organic semiconductor materials, which are widely used in the preparation of organic small molecules and polymer semiconductors as light-resistant and electron-deficient building blocks. At the same time, compared with the commonly used conjugated systems with C-C single bonds, the rigid frameworks have good delocalized frontier molecular orbitals, which eliminates the obstacles of rotational torsion to charge transport, and exhibits longer persistence lengths in organic The semiconductor direction has very important application prospects. Therefore, the synthesis of indoledione derivative-based polymer semiconductors with rigid backbones has important application value. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D519/00H01L51/00H01L35/24
CPCC07D487/04C07D519/00H10N10/856H10K85/656H10K85/6572Y02E10/549
Inventor 岳晚段傢耀朱修远
Owner SUN YAT SEN UNIV
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