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Benzoindenotriptycene and spirofluorene-benzoindenotriptycene derivatives and preparation method thereof

A technology of benzoindenotriptycene and triptycene, which is applied in the fields of benzoindenotriptycene and spirofluorene-benzoindenotriptycene derivatives and their preparation, which can solve development limitations and the difficulty of synthesis of dottycene quinone and other issues to achieve the effect of good thermal stability

Inactive Publication Date: 2011-12-28
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

However, dottylenones are not easy to synthesize, so the development of doptylenone chemistry has been greatly limited.

Method used

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  • Benzoindenotriptycene and spirofluorene-benzoindenotriptycene derivatives and preparation method thereof
  • Benzoindenotriptycene and spirofluorene-benzoindenotriptycene derivatives and preparation method thereof
  • Benzoindenotriptycene and spirofluorene-benzoindenotriptycene derivatives and preparation method thereof

Examples

Experimental program
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Embodiment

[0024] Preparation of 2,5-dimethoxyphenylacrylic acid (1)

[0025] Mix 2,5-dimethoxybenzaldehyde (5.00 g, 30.00 mmol) and malonic acid (4.20 g, 40.00 mmol), add 12 ml of pyridine and 1 ml of piperidine, protect under nitrogen, and reflux at 110°C for 4 hours, the reaction solution was cooled and poured into a mixture of 100 ml of ice water and 5 ml of 2 N hydrochloric acid at 0°C to precipitate a white flocculent substance, which was filtered by suction to obtain a crude product, recrystallized with absolute ethanol, and dried to obtain a white Solid (5.48 g, 87.4%) (chloroform / methanol=20 / 1; R f = 0.43); M.p.: 144-145 oC; literature value: 151-152°C;

[0026] 1 H NMR (CDCl 3 , 500 MHz, ppm) δ:8.08 (d, J = 16.1 Hz, 1 H), 7.07 (s, 1 H), 6.94 (d, J = 8.9 Hz, 1 H), 6.87 (d, J = 9.0 Hz, 1 H), 6.52 (d, J = 16.1 Hz, 1 H), 3.86 (s, 3 H), 3.80 (s, 3 H).

[0027] Preparation of 2,5-dimethoxyphenylpropionic acid (2)

[0028]Dissolve 2,5-dimethoxyphenylacrylic acid (1) (20....

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Abstract

The invention discloses benzindene triptycene and spirofluorene-benzindene triptycene derivatives, which is characterized by the heterocyclic linking of benzindene and triptycene quinone, and the linking of a spirofluorene benzindene group and triptycene quinone. The preparation method comprises the following four steps: oxidizing pre-synthesized 1,4-dimethoxy-11,11-diethyl benzo [b] fluorene and1,4-dimethoxy benzo [b] spirobifluorene which are used as important precursor compounds by an oxidant of ceric ammonium nitrate to obtain quinone, performing a Diels-Alder cycloaddition reaction of quinone-containing structural units and diene anthracene, converting the cycloaddition product into a triptycene phenol intermediate under a condition with hydrobromic acid as a catalyst and dioxane asa solvent, and oxidizing the product into triptycene quinone derivatives by iodobenzene acetate to obtain benzindene triptycene and spirofluorene-benzindene triptycene derivatives. Triptycene derivatives have a unique three-dimensional rigid structure, and triptycene quinone is an important triptycene derivative, so the material synthesized by the invention can exhibit special properties, and provides new selection for novel liquid crystal materials.

Description

technical field [0001] The invention relates to the field of novel liquid crystal materials, in particular to a class of benzoindenotriptycene and spirofluorene-benzoindenotriptycene derivatives and a preparation method thereof. Background technique [0002] Triptycene is a class of compounds with very interesting structural characteristics. It has a high degree of symmetry, and the angles between the three benzene rings are all 120 degrees, forming three open electron-rich cavities; it has a unique three-dimensional rigidity structure and easy functionalization. Triptycene is very electron-rich and is an ideal acceptor for providing π-electron stacking. [0003] Triptycene compounds have attracted everyone's attention due to their unique structure and performance, and have been used in the synthesis of molecular motors ([1] Keilytr et a1. Progress toward a rationally designed, chemically powered rotary molecular motor[J]. J. Am. Chem. Soc. 2007, 129(2): 376-386.); Molecul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/22C07C46/00C09K19/32
Inventor 刘乾才刘亮
Owner EAST CHINA NORMAL UNIV
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