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Helicene diphenol hydride, method for preparing same and application of helicene diphenol hydride

A technology for hydrogenating helicene diphenols and helicene diphenols, which is applied in the directions of organic chemistry methods, carbon-based compound preparation, chemical instruments and methods, etc. Symmetrical catalytic effect, correct structure, high product yield effect

Active Publication Date: 2016-06-01
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although many synthetic methods have been reported, the preparation of functionalized helicene, whether it is the preparation method of the helicene skeleton itself or the derivatization reaction of the skeleton, is still the main reason that limits the development of helicene.

Method used

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  • Helicene diphenol hydride, method for preparing same and application of helicene diphenol hydride
  • Helicene diphenol hydride, method for preparing same and application of helicene diphenol hydride
  • Helicene diphenol hydride, method for preparing same and application of helicene diphenol hydride

Examples

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Embodiment 1

[0071] Embodiment 1, the synthesis of 1,1 '-diphenyl [5] helical diphenol

[0072] 1,1'-diphenyl[5]helicenediol is synthesized according to the following reaction scheme:

[0073]

[0074] 1) Add 99g of tetralone, 100g of N-bromosuccinimide, 4g of ferric chloride and 500mL of acetonitrile in sequence in a 1000mL round bottom flask, react at room temperature for 4 hours, add 300mL of water to the reaction system, and precipitate a white solid 143 g of product B, greater than 99% yield.

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Abstract

The invention discloses helicene diphenol hydride, a method for preparing the same and application of the helicene diphenol. A structural formula of the helicene diphenol hydride is shown as a formula I, wherein an R represents hydrogen atoms or bromine atoms, and an R' represents hydrogen atoms or bromine atoms. The helicene diphenol hydride, the method for preparing the helicene diphenol hydride and the application have the advantages that raw materials are low in cost and easy to synthesize, the helicene diphenol hydride is high in product yield, easy to derive and good in stability, and methods for preparing gram-grade quantities of optically pure helicene molecules with excellent heat stability can be implemented.

Description

technical field [0001] The invention relates to a hydrogenated spirodenediphenol and its preparation method and application, and belongs to the field of design and synthesis of chiral catalysts. Background technique [0002] Helicene is a class of aromatic compounds with a helical structure formed by at least four aromatic (hetero) rings ortho-fused. As a class of π-conjugated systems, helicenes are used in molecular machines (T.B.Norsten; A.Peters, R.McDonald, M.T.Wang, N.R.Branda, Reversible[7]-thiahelicene formation using a1,2-dithienylcyclopentene photochrome, J.Am.Chem.Soc .2001, 123, 7447-7448), liquid crystals (C.Nuckolls, T.J.Katz, Synthesis, Structure, and Properties of a Helical Columnar Liquid Crystal, J.Am.Chem.Soc.1998, 120, 9541–9544), molecular dyes (A.Mishra, M.K.R. Fischer, P.Bauerle, Metal-freeorganicdyesfordye-sensitizedsolarcells:fromstructure:propertyrelationshipstodesignrules, Angew.Chem., Int.Ed., 2009,48,2474–2499) and other fields are widely used; u...

Claims

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Application Information

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IPC IPC(8): C07C39/17C07C39/42C07C45/63C07C49/755C07C41/30C07C43/225C07C43/21C07C303/26C07C309/65C07C37/04C07C37/62B01J31/02C07B53/00
CPCB01J31/0232C07B53/00C07C37/04C07C37/62C07C39/17C07C39/42C07C41/30C07C45/63C07C303/26C07C49/755C07C43/225C07C43/21C07C309/65
Inventor 陈传峰房蕾李猛
Owner INST OF CHEM CHINESE ACAD OF SCI
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