Oligothiophene functionalized ortho-carborane derivatives, and synthesis method and optical limiting application thereof

An oligomerized thiophene and a synthesis method technology, which can be applied in chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, optics, etc., and can solve problems such as limiting the practical application of materials and affecting the stability of devices or sensors. , to enrich assembly behavior, enhance solubility and processability, and facilitate charge transfer.

Active Publication Date: 2021-06-29
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because oligothiophene contains active S heteroatoms, lower highest occupied orbital (HOMO) energy and wider energy gap, it is easy to react with oxygen and water in the air under the irradiation of ultraviolet light or visible light, and the influence is mainly on it. The use stability of devices or sensors prepared by the foundation limits the practical application of such materials

Method used

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  • Oligothiophene functionalized ortho-carborane derivatives, and synthesis method and optical limiting application thereof
  • Oligothiophene functionalized ortho-carborane derivatives, and synthesis method and optical limiting application thereof
  • Oligothiophene functionalized ortho-carborane derivatives, and synthesis method and optical limiting application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 1. Synthesis of Compound 1

[0056] Under the protection of nitrogen, weigh 0.654g (2.0mmol) 5-bromo-2,2':5',2"-tripolythiophene (3T-Br), 46.2mg (0.04mmol) tetrakis (triphenylphosphine) Palladium, 7.6mg (0.04mmol) cuprous iodide and 0.236g (2.4mmol) trimethylsilyl acetylene were placed in a pressure-resistant tube, and 20mL triethylamine and 40mL tetrahydrofuran were added successively to the pressure-resistant tube, and heated to 60°C, stirred and reacted for 12 hours, cooled to room temperature, spin-dried, and carried out column chromatography with a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:20 as the eluent and dried to obtain 0.42 g of bright yellow solid compound 1, Productive rate is about 62%.Its reaction equation is as follows:

[0057]

[0058] The structural characterization data of the obtained compound 1 is: 1 H NMR (CDCl 3 ,400MHz)δ:7.23(dd,J=5.1,1.1Hz,1H),7.17(dd,J=3.6,1.1Hz,1H),7.12(d,J=3.8Hz,1H),7.07(s,2H ),7.02(dd,J=5...

Embodiment 2

[0068] 1. Synthesis of compound 3-1

[0069] Under nitrogen protection, weigh 0.27g (1.0mmol) compound 2, 23.1mg (0.02mmol) tetrakis (triphenylphosphine) palladium, 3.8mg (0.02mmol) cuprous iodide and 0.391g (1.2mmol) 5- Bromo-2,2′:5′,2″-tripolythiophene (3T-Br) was placed in a pressure-resistant tube, and 20 mL of triethylamine and 40 mL of tetrahydrofuran were added to the pressure-resistant tube in turn, heated to 90°C, and stirred Reacted for 12 hours, cooled to room temperature, spin-dried, carried out column chromatography separation and drying with dichloromethane and sherwood oil volume ratio 2:1 mixture as eluent, obtained yellow solid compound 3-1.Its reaction equation is as follows:

[0070]

[0071] 2. Synthesis of oligothiophene functionalized ortho carborane derivatives 4-2

[0072] Under nitrogen protection, weigh 0.244g (2.0mmol) decaborane (B 10 h 14 ) into a pressure-resistant tube, add 42 mL of anhydrous toluene and 0.13 mL of N,N-dimethylaniline, stir...

Embodiment 3

[0077] The use of oligothiophene functionalized ortho carborane derivatives obtained in Example 1 and Example 2 as optical limiting materials

[0078] The oligothiophene functionalized ortho-carborane derivatives 4-1 and 4-2 were prepared with THF to a concentration of 1.0×10 - 2 mol / L solution, ultrasonic treatment for 3 to 5 minutes, and the color of the solution is a yellow solution.

[0079] Figure 17 is the two-photon absorption cross-section value of the oligothiophene-functionalized ortho-carborane derivatives 4-1 and 4-2 in the range of 620nm to 850nm. From the figure, we can see that the oligothiophene-functionalized ortho-carborane The maximum two-photon absorption cross section value of alkane derivative 4-1 is 104GM at 650nm, and the nonlinear absorption coefficient can be calculated to be about 2.0×10 -2 cm / GW; the maximum two-photon absorption cross section value of oligothiophene functionalized ortho-carborane derivative 4-2 is 118GM at 650nm, and the nonlin...

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Abstract

The invention discloses oligothiophene functionalized ortho-carborane derivatives as well as a synthesis method and an optical limiting application thereof, and belongs to the technical field of organic light-emitting materials. The oligothiophene functionalized ortho-carborane derivative is simple in synthesis method and relatively high in yield, has excellent properties of both oligothiophene and carborane, also has rich assembly behaviors, overcomes the defect of fluorescence weakening or quenching caused by oligothiophene molecule aggregation, has typical aggregation-induced emission properties, and can be used in the field of fluorescence detection. Meanwhile, the compound is relatively large in Stokes shift and high in chemical stability and machinability, shows relatively high two-photon third-order nonlinear optical response, can be applied to the fields of optical limiting, organic luminescence, biological fluorescent probes, chemical sensing and the like, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a class of oligothiophene functionalized ortho-position carborane derivatives, a synthesis method thereof and the application of light limiting characteristics. Background technique [0002] Aggregation-induced emission (AIE) materials have attracted people's attention because of their unique enhanced photoluminescence behavior in solid state and thin film state, which overcomes the fluorescence cluster quenching problem encountered by traditional organic fluorescent molecules, and its new molecular structure design and preparation , Function development is still the hot spot of current scientific research work. Oligothiophene is a kind of electron-rich π-conjugated compound with excellent photoelectric properties; as the degree of π-electron conjugation increases, the fluorescence emission wavelength of oligothiophene shifts red, and the Stokes ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05C09K11/06G02F1/355
CPCC07F5/05C09K11/06G02F1/3551C09K2211/1092C09K2211/1096Y02E10/549
Inventor 刘太宏冯婉刘科房喻
Owner SHAANXI NORMAL UNIV
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