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
View PDF2 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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
Comparison scheme
Effect test

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....

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/22C07C46/00C09K19/32
Inventor 刘乾才刘亮
Owner EAST CHINA NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap