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Fluoradene derivative and preparation method thereof

A technology of derivatives and compounds, applied in the field of Fluoradene derivatives and their preparation, can solve problems not involving synthesis details, etc., and achieve good thermal stability

Inactive Publication Date: 2011-04-27
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of 7b position substituted derivatives of Fluorandene has not been reported yet, so far only the crystal structures of two compounds 7b-triisopropylsilylfluorandene and 7b-(2,4-dinitrophenyl)-fluorandene have been reported, but no specific Synthetic details of ([4] (a) A.Xia, J.P.Selegue, A.Carrillo, B.O.Patrick, S.Parkin and C.P.Brock, Acta Crystallographica 2001, B57, 507; (b) L.Fabian and A.Kalman, Acta Crystallographica 2004, B60, p548; (c) C.P. Brock, and B.O. Patrick, Mol. Cryst. Liq. Cryst. 2002, 389, 79.)

Method used

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  • Fluoradene derivative and preparation method thereof
  • Fluoradene derivative and preparation method thereof
  • Fluoradene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1), the preparation of 2-bromoiodobenzene (1)

[0039] Dissolve o-bromoaniline (5g, 29.06mmol) in 50mL of water, then add 15mL of concentrated hydrochloric acid into it, and cool to 0°C. NaNO 2 (2.41g, 34.87mmol) was dissolved in 50mL of water and slowly added dropwise to the above solution. After all the solids were dissolved, KI (7.23 g, 43.59 mmol) dissolved in 11 mL of water was slowly added to the above solution, and the solution turned blood red. Stir at room temperature for 0.5h. Stir at 70°C for 0.5h. Cool, add 0.43mol / L Na 2 SO 3 Neutralize 20mL of the solution. Extracted with dichloromethane, the organic phase was washed with water, and then passed through anhydrous MgSO 4 dry. After suction filtration, the solvent was removed, and then distilled under reduced pressure to obtain a light yellow liquid (3.85 g, yield: 77.0%). 1 H NMR (CDCl 3 , 500MHz): δ7.88-7.86(dd, J=8.0Hz, J=1.4Hz 1H); 7.64-7.62(dd, J=8.0Hz, J=1.4Hz, 1H); 7.30-7.20(td, J =7.9Hz, J=...

Embodiment 2

[0050] 1) with (1) in embodiment 1

[0051] 2) with (2) in embodiment 1

[0052] 3) Preparation of 9-hexylcarbazole (5)

[0053] Under nitrogen protection, NaH (1.74g, 60%w / w dispersion in mineral oil, 44.0mmol) was poured into a round bottom flask containing 20mL N, N-dimethylacetamide, N 2 Protect. Carbazole (5.52 g, 33.0 mmol) was dissolved in 60 mL of N,N-dimethylacetamide and added dropwise to the above solution and stirred for 0.5 h. Add 1-bromohexane (6.54g, 39.6mmol) dropwise to it, and heat to reflux for 5h. Pour into water after cooling, extract with dichloromethane (3×50mL), and use MgSO for the organic phase 4 Dry, filter and spin dry. Recrystallization from ethanol gave a white solid (6.39 g, yield 77.0%). MP: 64-66°C

[0054] 4) Preparation of 3-(9-(2-bromophenyl)fluorenyl)-9-hexylcarbazole (6)

[0055]Under nitrogen protection, N-hexylcarbazole (2.80g, 11.12mmol) and trifluorosulfonic acid (0.67g, 4.45mmol) were dissolved in 10mL1,4-dioxane, and then 9-(...

Embodiment 3

[0063] 1) with (1) in embodiment 1

[0064] 2) with (2) in embodiment 1

[0065] 3) with (3) in embodiment 2

[0066] 4) Preparation of 3,6-bis[9-(2-bromophenyl)fluorenyl]-9-hexylcarbazole (8)

[0067] Under nitrogen protection, N-hexylcarbazole (1.29g, 5.19mmol) and 9-(2-bromophenyl)-9-fluorenol (3.5g, 10.37mmol) were dissolved in 50mL 1,4-dioxane , and then trifluorosulfonic acid (1.48g, 9.86mmol) was slowly dropped into the above solution, and then heated to 80°C for 5h. After cooling, the reaction solution was poured into water, filtered with suction, and dried. Through the column with petroleum ether:dichloromethane=4:1, a white solid (2.0 g, yield 43.3%) was obtained.

[0068] 1 H NMR (CDCl 3 500MHz): δ7.75(s, 4H); 7.69(br, 2H); 7.59(s, 2H); 7.51(d, J=7.0Hz, 4H); 7.40-7.36(m, 6H); 7.25(t , J=7.5Hz, 4H); 7.19(d, J=9.0Hz, 2H); 7.12-7.08(m, 4H); 7.06-7.03(m, 2H); 4.14(t, J=7.5Hz, 2H) ;1.76-1.72(m, 2H); 1.30-1.23(m, 6H); 0.83(t, J=7.0Hz, 3H).

[0069] 13 C NMR (CD...

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Abstract

The invention discloses a fluoradene derivative and a preparation method thereof. The preparation method comprises the following steps of: introducing fluoradene rings into compounds, namely carbazole, hexyl carbazole, triphenylamine and hexyl triindole; and catalyzing intramolecular carbon-hydrogen bond activation and hydrogen halide elimination reaction through palladium and efficiently constructing a carbon ring or a heterocyclic compound, particularly constructing the carbon ring with a novel structure. The invention aims to synthesize and characterize a fluoradene structural unit-containing large-tension cyclic compound; and the novel fluoradene structural unit-containing compound is expected to be used in the field of organic photoelectric materials.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a class of Fluoradene derivatives and a preparation method thereof. Background technique [0002] In synthetic organic chemistry, highly strained aromatic ring molecules such as tetracyclononane are extremely challenging both theoretically and experimentally. Among them, fluoradene (attached figure 1 In a), an acidic molecule with two indene rings sharing a quaternary carbon. Structural analysis of Fluradene was derived from the unknown hydrocarbon C 19 h 10 (attached figure 1 In b) ([1]A.Streiweiser Jr.Tetrahedron Lett.1960, (6), 23.) the C-C bond of the aromatic ring is inspired. So far, there are very few reports on fluorandene ([3](a) H.Rapoprt, and G.Smolinsky, J.Am.Chem.Soc.1958, 80, 2910; (b) H.Rapoprt, and G .Smolinsky, J.Am.Chem.Soc.1960, 82, 934; (c) G.Baum and H.Shecter, J.Org.Chem.1976, 41, 2120; (d) H.Dietrich, D.Bladauski , M.Grosse, K.Roth...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D487/14C07C211/56C07C209/68C09K11/06
Inventor 刘乾才戎玲玲
Owner EAST CHINA NORMAL UNIV
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