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Material contg. thiophene spirane structure, its synthesis and application

A thiophene spiro, meaning technology, applied in the field of thiophene spiro ring materials and their preparation, can solve the problems of no articles and patent reports, etc.

Inactive Publication Date: 2006-04-12
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there are no articles and patent reports on the material system containing thiophene spiro ring

Method used

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  • Material contg. thiophene spirane structure, its synthesis and application
  • Material contg. thiophene spirane structure, its synthesis and application
  • Material contg. thiophene spirane structure, its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Embodiment 1, preparation of dithiophene spiro compound material by Friedel-Craft ring closure reaction:

[0111] Spiro[pentacyclo[1,2-b:4,3-b′]dithiophene-7,9′-fluorene]

[0112] spiro[cyclopenta[1,2-b:4,3-b′]dithiophene-7,9′-fluorene]

[0113] 2-bromo-3,3-dithiophene

[0114] Take 2.075g (12.5mmol) of 3,3-dithiophene and dissolve it in DMF (17.42ml), and dissolve 2.046g (11.5mmol) of NBS in DMF (21.78ml), and add dropwise under ice water to mix the reaction. Stir at room temperature for 24 hours, dilute with ice water, extract with ether, dry and rotary evaporate, and purify with petroleum ether silica gel column to obtain 2.53 g of light yellow liquid 2-bromo-3,3-dithiophene (82.9% yield).

[0115] GC-MS (EI-m / z): 244 / 246 (M + ); 1 H NMR (400MHz, CDCl 3 , ppm): δ7.084-7.098 (d, J=5.6Hz, 1H), 7.277-7.291 (d, J=5.6Hz, 1H), 7.377-7.396 (dd, J=4.8Hz, J=2.8Hz, 1H), 7.431-7.447(dd, J=4.8Hz, J=1.2Hz, 1H), 7.635-7.645(dd, J=2.8Hz, J=1.2Hz, 1H).

[0116] Spiro[pentacyclo...

Embodiment 2

[0125] Example 2. Preparation of monothiophene spiro compound materials by Friedel-Craft ring closure reaction:

[0126] Spiro[indene[2,1-b]dithiophene-8,9′-fluorene]

[0127] spiro[indeno[2,1-b]thiophene-8,9′-fluorene]

[0128] 2-Bromo-3-phenylthiophene

[0129] Take 3-phenylthiophene (2g, 12.5mmol) and dissolve it in DMF (17.42ml), and dissolve NBS (2.046g, 11.5mmol) in DMF (21.78ml), add it dropwise under ice water and mix the reaction. Stir at room temperature for 24 hours, dilute with ice water, extract with ether, dry and rotary evaporate, and purify with petroleum ether silica gel column to obtain 2.20 g of light yellow liquid 2-bromo-3-phenylthiophene (80% yield).

[0130] GC-MS (EI-m / z): 238 / 240 (M + ); 1 H NMR (400MHz, CDCl 3 , ppm): δ7.064-7.081 (d, J = 5.6Hz, 1H), 7.317-7.335 (d, J = 5.2Hz, 1H), 7.385-7.428 (m, 1H), 7.463-7.502 (t, J =8.0Hz, 2H), 7.595-7.619(d, 3 J=8.0Hz, 2H). 13 C NMR (CDCl 3 , ppm): 108.922, 126.205, 127.966, 128.697, 128.964, 129.444, 1...

Embodiment 3

[0140] Embodiment 3, prepare thiophene spiro compound material by Suzuki coupling reaction:

[0141] 2′,7′-Diphenylspiro[pentane[1,2-b:4,3-b′]dithiophene-7,9′-fluorene]

[0142] 2′,7′-diphenylspiro[cyclopenta[1,2-b:4,3-b′]dithiophene-7,9′-fluorene]

[0143] 2′,7′-Dibromospiro[pentane[1,2-b:4,3-b′]dithiophene-7,9′-fluorene]

[0144] 2′,7′-dibromospiro[7H-cyclopenta[1,2-b:4,3-b′]dithiophene-7,9′-[9H]fluorene]

[0145] Get 2-bromo-3,3-dithiophene 1g (4.2mmol) and magnesium Mg 0.1004g (4.2mmol) reaction generates Grignard reagent, and 2,7-dibromofluorene copper 1.414g (4.2mmol) in 16mL tetrahydrofuran React at 60°C for 12 hours, a large amount of white precipitate is formed, and finally add saturated NHCl 4 Convert Grignard salts to alcohols. Ether extraction, drying and rotary evaporation, petroleum ether: dichloromethane mixed solvent (3:2) silica gel column purification, to obtain a slightly pale yellow white solid 2,7-dibromo-9-(2-(3-(3- Thienyl) thienyl))-fluorene-9-alco...

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Abstract

This invention belongs to photo-electricity field, particularly a kind of thiophene spiral ring material and its preparation method, and its application in organic flat plate display, photo-volt cells, organic field effect tube and laser etc. organic electron field. This kind of compound introduces thiophene and functional thiophene in to conjugate semi-conductor material through spiral ring structure. The virtue are: (1) the synthesis is convenient and easy to get, and may be further modified; (2) may effectively realize photo-electricity property of modulate material; (3) with the virtue of high spectrum stability of spiral difluorene structure. The luminescence apparatus incurred by electricity prepared with this invent material has satisfaction result in brightness and luminescence efficiency. Thiophene spiral ring will be a potential commercialised photo-electricity material.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a thiophene spiro ring material and a preparation method thereof, and relates to the application of these luminescent materials in the fields of organic electroluminescence, organic field effect tube, organic solar cell, nonlinear optics, biosensing, laser and the like. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A. Appl. Phys. Lett. Marks, R.N.; Mackay, K.; Friend, R.H.; Burn, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (Polymeric Light-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, other organic electronics and optoelectronic industries, ...

Claims

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Application Information

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IPC IPC(8): C07D333/50C07D495/10C07D495/22C07D498/10C07D513/10H05B33/14C09K11/06
Inventor 黄维解令海侯晓雅
Owner FUDAN UNIV
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