Fluorene derivatives and their application

A compound and group technology, applied in the field of novel fluorene derivatives, can solve the problems of limited application, weak two-photon absorption, limited application by thermal stability and photochemical stability, and achieve easy use and good solubility. Effect

Inactive Publication Date: 2005-09-14
SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the two-photon absorption properties of most current molecules are relatively weak, which limits the application in optical limiting devices
Recently, a series of two-photon absorbing dyes have been reported (references: [10] Prusud P N, Bhawalker J D, et al. US Patent, US6402037, 2002-06-11; [11] Seth Marder, Joseph Perry. US Patent, US6267913B1 , 2001-7-31), among the reported phenylethylene dyes and stilbene dyes, their two-photon absorption cross-sections are medium-sized, and their limited thermal and photochemical stability limits their applications.

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
  • Fluorene derivatives and their application
  • Fluorene derivatives and their application
  • Fluorene derivatives and their application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 1,1'-(9,9-bis(2-ethylhexyl)-2,7-fluorenyl-2,1-divinyl)bis(4-methoxy)benzene

[0031] Step 1

[0032] Synthesis of 9,9-bis(2-ethylhexyl)fluorene

[0033] Fluorene (34 g, 0.205 mol), potassium hydroxide (56 g, 1.0 mol), and potassium iodide (3.4 g, 0.02 mol) were added to 150 ml of DMSO, stirred to dissolve, and then (2-ethylhexyl) bromide was added dropwise (96ml, 103.5g, 0.536mol), the temperature was raised to 25°C and stirred for 24 hours. After the reaction, the mixture was poured into water, separated, washed, dried, concentrated, and then distilled under reduced pressure to obtain a crude product. Further purification by column chromatography on silica gel gave 9,9-bis(2-ethylhexyl)fluorene, 74.4 g, with a yield of 93%.

[0034] Step two:

[0035] Synthesis of 2,7-dibromo-9,9-bis(2-ethylhexyl)fluorene

[0036] Add 9,9-bis(2-ethylhexyl)fluorene (18.35 g, 0.047 mol) and iodine (0.12 g, 0.47 mmol) prepared in the above step into 170 ml of dichloro...

Embodiment 2

[0041] Synthesis of 1,1'-(9,9-diethyl-2,7-fluorenyl-2,1-divinyl)bis(4-methoxy)benzene

[0042] Step 1:

[0043] Synthesis of 9,9-diethylfluorene

[0044]The step is the same as step 1 in Example 1, except that (2-ethylhexyl) bromine is changed to bromoethane (40ml, 58.4 grams, 0.536mol) to obtain 9,9-diethylfluorene, 43.26 grams, product The rate is 95%.

[0045] Step two:

[0046] Synthesis of 2,7-dibromo-9,9-diethylfluorene

[0047] The step is the same as step 2 in Example 1, except that 9,9-bis(2-ethylhexyl)fluorene is changed into 9,9-diethylfluorene (10.44 grams, 0.047mol) to obtain 2,7-bis Bromo-9,9-diethylfluorene, 15.2 g, 85% yield.

[0048] Step three:

[0049] Synthesis of 1,1'-(9,9-diethyl-2,7-fluorenyl-2,1-divinyl)bis(4-methoxy)benzene

[0050] The steps are the same as step 3 in Example 1, except that 2,7-dibromo-9,9-bis(2-ethylhexyl)fluorene is changed to 2,7-dibromo-9,9-diethylfluorene (6.27 g, 16.5 mmol) to give 1,1'-(9,9-diethyl-2,7-fluorenyl-2,1-di...

Embodiment 3

[0052] Synthesis of 1,1'-(9,9-bis(dodecyl)-2,7-fluorenyl-2,1-divinyl)bis(4-methoxy)benzene

[0053] Step 1:

[0054] Synthesis of 9,9-Di(dodecyl)fluorene

[0055] Step is the same as step 1 in example 1, and difference is that (2-ethylhexyl) bromide is changed into dodecyl bromide (130ml, 133.6 grams, 0.536mol), obtains 9,9-bis(dodecyl) Fluorene, 104 g, yield 90%.

[0056] Step two:

[0057] Synthesis of 2,7-dibromo-9,9-di(dodecyl)fluorene

[0058] The step is the same as step 2 in Example 1, except that 9,9-bis(2-ethylhexyl)fluorene is changed into 9,9-bis(dodecyl)fluorene (23.62 grams, 0.047mol) to obtain 2 , 7-dibromo-9,9-bis(dodecyl)fluorene, 25.46 g, yield 82%.

[0059] Step three:

[0060] Synthesis of 1,1'-(9,9-bis(dodecyl)-2,7-fluorenyl-2,1-divinyl)bis(4-methoxy)benzene

[0061] The step is the same as step 3 in Example 1, except that 2,7-dibromo-9,9-bis(2-ethylhexyl)fluorene is changed to 2,7-dibromo-9,9-bis(dodecyl) Alkyl)fluorene (10.9 g, 16.5 mmol) to giv...

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 relates a novel fluorenes derivative with formula (I), wherein R is C2-C12 straight chain or branched chain alkyl, E is electron donor group or electron acceptor group. The invention also relates to the use of the compound as dyestuff in optical amplitude limiting.

Description

Technical field: [0001] The invention relates to a novel fluorene derivative and the application of the compound as a dye in light limiting. Background technique: [0002] In recent years, organic materials, especially those with excellent nonlinear optical properties, have received great attention due to their numerous applications in optical devices. Among them, the optical limiter used for the protection of human eyes and optical sensors has attracted the interest of many scientific researchers. An ideal optical limiter requires that the material has a small linear absorption within the wavelength range used, and when the light intensity increases to a certain level, the material can absorb a large amount of incident energy, while keeping the transmitted light intensity within a certain range. To achieve the purpose of protecting human eyes and optical sensors. Organic two-photon materials are a class of materials with special functions. They jump to the excited state b...

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 Patents(China)
IPC IPC(8): C07C13/567C07C25/24C07C43/235C07C63/66C07C211/45C07D207/26C07D207/40C07D209/48C07D209/82C07D213/16C07D251/18C07F9/40C09B69/00C09K11/06G02F1/361
Inventor 马文波吴谊群顾冬红于福熹
Owner SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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