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Electrochromic compounds

a technology of electrochromic devices and compounds, applied in the field of electrochromic devices, can solve problems such as preventing efficient decolouration of electrochromic devices

Inactive Publication Date: 2009-10-15
NTERA LTD (IE)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0061]Step (f) is carried out when a compound of formula I is required wherein X− is other that Br− or Cl−. The conversion of X′ to X″ is effected by reacting a compound of formula I′ with a salt of the desired balancing ion in aqueous solution. Conversion of X′ to X″ can confer greater stability and greater solubility of the chromophore in a wider range of solvents, resulting in the use of less concentrated solutions in electrochromic devices with consequent reduction in costs.

Problems solved by technology

However, in conventional viologen-based systems, diners may be formed due to the parallel overlap of viologens, thereby preventing efficient decolouration in the electrochromic device.

Method used

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  • Electrochromic compounds
  • Electrochromic compounds
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Examples

Experimental program
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Effect test

example 2

Synthesis of 1-Phosphonoethyl-1′-(3-propylphenyl)-4,4′-bipyridinium bis-hexafluorophosphate (Compound 2)

[0068]A solution of ammonium hexafluorophosphate (5 g) in water (20 ml) was added to a cold solution of 1-phosphonoethyl-1′-(3-propylphenyl)-4,4′-bipyridinium dichloride (2 g) prepared in Example 1 in water (20 ml), A precipitate of 1 -phosphonoethyl-1′-(2,4,6-trimethylphenyl)-4,4′-bipyridinium bis-hexafluorophosphate (3 g) formed immediately and was filtered, washed with cold water and dried.

example 3

Synthesis of 1-Phosphonoethyl-1′-(2,4,6-trimethylphenyl)-4,4′-bipyridinium dichloride (Compound 3)

(i) Synthesis of 1-(Diethyl ethylphosphonate)-4,4′-bipyridinium bromide

[0069]4,4′-Bipyridine (100 g, 0.64 moles) and diethyl bromoethylphosphonate (157 g, 0.64 moles) in toluene (500 ml) in a 1 L round bottomed flask was refluxed until the solid precipitate of the monocation salt was formed. The precipitate was filtered hot. The filtrate was refluxed again and the process repeated until no more solid formed. A yield of 95 g of the monocation was obtained.

(ii) Synthesis of 1-Diethyl ethylphosphonate-1′-(2,4-dinitrophenyl)-4,4′-bipyridinium monobromide monochloride

[0070]1-Diethyl ethylphosphonate-4,4′-bipyridinium monobromide (50 g, 0.12 moles) was added to acetonitrile (400 ml) in a 1 L round-bottomed flask and refluxed for thirty minutes. The clear solution was decanted into a 1 L round-bottomed flask and 2,4-dinitrochlorobenzene (150 g, 0.74 moles) was added and refluxed for eighteen h...

example 4

Synthesis of 1-phosphonoethyl-1′-(2,4,6-trimethylphenyl)-4,4′-bipyridinium bis-hexafluorophosphate (Compound 4)

[0074]A solution of ammonium hexafluorophosphate (4.3 g) in water (20 ml) was added to a solution of 1-phosphonoethyl-1′-(2,4,6-trimethylphenyl)-4,4′-bipyridinium dichloride (2 g) prepared in Example 3 in water (20 ml). A precipitate of 1-phosphonoethyl-1′-(2,4,6-trimethylphenyl)-4,4′-bipyridinium bis-hexafluorophosphate (2.5 g) formed immediately and was filtered and dried.

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Abstract

The invention concerns electrochromic compounds of the general formula I. These compounds may be used in electrochromic devices, especially electrochromic devices comprising nanostructured films.

Description

FIELD OF THE INVENTION[0001]This invention relates to novel electrochromic compounds. These compounds are useful in electrochromic devices such as electric windows, displays and other optical devices that can change colour according to the needs of the user. In particular, the compounds may be used in electrochromic devices comprising nanostructured films.BACKGROUND[0002]Viologen compounds, i.e. compounds which have a dipyridinium group and are capable of reversible reduction / colouration, are widely used in electrochromic devices. However, in conventional viologen-based systems, diners may be formed due to the parallel overlap of viologens, thereby preventing efficient decolouration in the electrochromic device.SUMMARY OF THE INVENTION[0003]It is an object of the invention to avoid or minimise the disadvantages of the prior art.[0004]According to the present invention there are provided compounds of the general formula IR1 is —(CH2)m—wherein m is zero or an integer from 1 to 10; or ...

Claims

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Application Information

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IPC IPC(8): C07F9/38C07D213/22C07D401/14C09K9/02G02F1/15
CPCC09K9/02C07D213/22G02F1/15C09K2211/1029
Inventor CORR, DAVIDRAO, S. N.STOBIE, NIALLKINSELLA, MARK
Owner NTERA LTD (IE)
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