Preparation of asymmetric cyanine dyes for DVD-R CD

A technology for asymmetric cyanine dyes, applied in the field of preparation of asymmetric cyanine dyes, can solve the problems of difficult purification and low purity, and achieve the effects of high purity of raw materials, good solubility and high yield

Inactive Publication Date: 2004-05-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The purpose of this invention is to provide a new method for preparing trimethine asymmetric cyanine dyes, which uses intermediate 1,1-dimethyl-2-formyl methylene-3-alkyl-1H-benzo [e] Indole is a raw material, reacts with substituted 1-alkyl-2,3,3-trimethylindole salt, and obtains a high-purity asymmetric cyanine dye through one recrystallization, to overcome the inadequacy of prior art synthesis Symmetrical dyes are difficult to purify, the purity is not high, and they cannot meet the defects of DVD-R disc recording media.

Method used

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  • Preparation of asymmetric cyanine dyes for DVD-R CD
  • Preparation of asymmetric cyanine dyes for DVD-R CD
  • Preparation of asymmetric cyanine dyes for DVD-R CD

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of Dye CY-3-1:

[0041]

[0042] Put 15g 1,1-dimethyl-3-butyl-2-formylmethylene-1H-benzo[e]indole, 17-6g 2,3,3-trimethyl-1-butyl Put -3H-indole iodide salt and 150ml acetic anhydride into a three-neck flask, start stirring, and heat to 105-110°C for 1 hour to react. Then, the reaction solution was slowly poured into 120ml of water under stirring, and the stirring was continued until a loose red solid was precipitated, filtered, washed with water for 2 to 3 times, and the filtered solid was dried. The solid was dissolved in methanol under heating and reflux, 18 g of sodium perchlorate crystals were added, the reflux was continued for 1 hour, and the product was naturally cooled to room temperature, 4.9 g of the product was crystallized, and the yield was 87%.

[0043] m.p.199~201℃.

[0044] 1 H-NMR (d 6 -DMSO) (ppm):

[0045] 0.97(t, 6H), 1.46(m, 4H), 1.75(m, 10H), 1.99(s, 6H), 4.14(t, 2H), 4.28(t, 2H), 6.55(t, 2H), 7.31 (m, 1H), 7.46(d, 1H), 7.55(t, 2...

Embodiment 2

[0047] Synthesis of Dye CY-3-2:

[0048]

[0049] Replace 2,3,3-trimethyl-1-butyl-3H-indole iodide in Example 1 with 1,2,3,3-tetramethyl-3H-indole iodide, other and implementation Example 1 is the same, and the yield is 89%.

[0050] m.p.142-144°C.

[0051] 1 H-NMR (d 6 -DMSO) (ppm):

[0052] 0.94(t, 3H), 1.45(m, 2H), 1.73(m, 8H), 1.96(s, 6H), 3.65(s, 3H), 4.24(t, 2H), 6.50(m, 2H), 7.29 (m, 1H), 7.44(d, 2H), 7.52(t, 1H), 7.66(t, 2H), 7.78(d, 1H), 8.08(m, 2H), 8.30(d, 1H), 8.46( t, 1H).

Embodiment 3

[0054] Synthesis of Dye CY-3-3:

[0055]

[0056] Put 15.5g 1,1-dimethyl-3-butyl-2-formylmethylene-1H-benzo[e]indole, 20g 5-chloro-2,3,3-trimethyl-1 -Butyl-3H-indole iodide salt and 150ml of acetic anhydride were put into a three-neck flask, started stirring, and heated to 105-110°C for 1 hour to react. Then slowly pour the reaction solution into a solution formed by dissolving 24g of potassium hexafluorophosphate in 120ml of water under stirring, and continue stirring until a loose red solid precipitates, filter, wash with water 2 to 3 times, and dry. The solid was dissolved in methanol under reflux, and naturally cooled to room temperature, 30.5 g of the product was crystallized, with a yield of 86%.

[0057] m.p.220~222℃.

[0058] 1 H-NMR (d 6 -DMSO) (ppm):

[0059] 1.01(m, 6H), 1.63(m, 4H), 1.74(s, 6H), 1.85(m, 2H), 1.92(m, 2H), 2.01(s, 6H), 4.24(t, 2H), 4.45 (t, 2H), 7.01(d, 1H), 7.32(s, 1H), 7.35(d, 1H), 7.42~7.44(m, 2H), 7.50~7.57(m, 2H), 7.63(t, 1H) ), 7.97 (...

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Abstract

The present invention discloses a new method for synthesizing asymmetric cyanine dyestuff. Said method comprises reacting 1,1-dimethyl-2-formylmethene-3-alkyl-1H-benzo[e] indole as raw material with substituted 1-alkyl-2,3,3,-trimethyl indole salt. The asymmetric cyanine dyestuff synthesized by using said invented method is high in purity (up to above 99%) and high in yield (greater than 85%), and convenient for purification (using recrystallizing process), and its extinction coefficient is large (epsilon is greater than 10 to the powr 5 M.cm), and its solubility is good in organic solvent and alcohol. It is specially applicable of using as recording medium of DNA-R optic disk.

Description

technical field [0001] The invention relates to a preparation method of an asymmetric cyanine dye for a DVD-R disc, in particular to a preparation method of an asymmetric trimethylcyanine dye. Background technique [0002] Cyanine dye is a kind of important organic dyestuff, has extensive application in the fields such as textile, photosensitive science, laser, fluorescent probe and disc record, because the n value of asymmetric cyanine dye is bigger, and k value is appropriate (US5,976,658 ; US 5,773,193), and thus can be made into a high-quality recordable optical disc as an optical disc recording medium. The absorption wavelength of trimethine asymmetric cyanine dye is compatible with the laser wavelength of DVD, so it is especially suitable as the recording medium of DVD-R disc. [0003] Starting from the first read-only compact disc CD (compact disc) launched by SONY and PHILIPS in 1982, the optical disc has developed rapidly as a large-capacity, long-life, and low-cos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C07D209/90C07D403/06C09B23/02
Inventor 孟凡顺苏建华杨松杰田禾陈孔常
Owner EAST CHINA UNIV OF SCI & TECH
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