Tetrahydro quinoline functional dye containing thiophene bridge chain

A tetrahydroquinoline and dye technology, applied in organic dyes, azo dyes, and analysis by chemical reaction of materials, etc., to achieve the effects of high fluorescence quantum yield, long excited state lifetime, and good chemical stability

Inactive Publication Date: 2008-04-30
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
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Problems solved by technology

By introducing suitable ligands or reactive groups on the Ru bipyridine complex structure to combine with ions or biomacromolecules, it can be detected by photoluminescence or electrochemiluminescence, and its detection sensitivity can reach 10 -13 to 10 -7 M (A.J.Bard, et al.Anal.Chem., 1984,56,2413), but pure organic electrochemiluminescent fluorescence detection reagents are rarely reported

Method used

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  • Tetrahydro quinoline functional dye containing thiophene bridge chain
  • Tetrahydro quinoline functional dye containing thiophene bridge chain
  • Tetrahydro quinoline functional dye containing thiophene bridge chain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 6-[5-(2-cyanoacrylate)thiophene-2-vinyl]-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

[0030]Before each step of reaction, the experimental device was evacuated, and the instrument was preheated to drive off water vapor.

[0031] (1) Synthesis of 6-formyl-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

[0032]

[0033] Add 1.7g (9mmol) 1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline and 3mL dry DMF into the flask under the protection of nitrogen, keep the temperature at 10-20°C In between, add 0.9mL of phosphorus oxychloride dropwise, heat to 50°C and keep warm for 3-4 hours after the dropwise addition; cool, add 50g of crushed ice cubes, stir well; add dilute sodium hydroxide solution to neutralize , a large amount of solid product was precipitated, filtered and dried to obtain compound 6-formyl-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline 1.3g (6mmol), yield 66.7% .

[0034] NMR 1 H-NMR (CDCl 3 , 400MHz, ppm): δ1.28(s, 3H), 1.34(s, 3H), 1....

Embodiment 2

[0056] Synthesis of 6-[5-(2-diethylphosphoacrylocyano)thiophene-2-vinyl]-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

[0057]

[0058] 65mg (0.2mmol) 6-(5-formylthiophene-2-vinyl)-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline and 43mg (0.24mmol ) Diethyl cyanomethyl phosphate is added in the flask, acetonitrile is used as a solvent, and 6 to 8 drops of piperidine are added dropwise as a catalyst; heated to reflux for 3 hours, and the solvent is removed after reflux ends, and dichloromethane: ethyl acetate=15:1 The solvent of (v / v) is carried out column separation and purification on the silica gel column as eluent, obtains compound 6-[5-(2-diethyl phosphate acrylocyano) thiophene-2-vinyl]-1,2, 75 mg (0.15 mmol) of 2,4-tetramethyl-1,2,3,4-tetrahydroquinoline, yield 77.5%.

[0059] Melting point: 112-113°C;

[0060] NMR 1 H-NMR (Acetone-d 6 , 400MHz, ppm): δ1.24(s, 3H), 1.33(s, 3H), 1.34-1.39(m, 9H,), 1.47(dd, 1H), 1.87(dd, 1H), 2.80-2.89( m, 4H), 4.14-4.21(m, 4H),...

Embodiment 3

[0066] Synthesis of 6-{2-[5-(2-diethylphosphoacrylocyano)thienyl]}-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

[0067] (1) Synthesis of 6-bromo-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

[0068]

[0069]Dissolve 368mg (2mmol) of 1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline in 20mL carbon tetrachloride, add 392mg (2.2mmol) NBS and 185 mg (1.1 mmol) of azobisisobutyronitrile, heated to reflux, and the reaction was completed in 30 minutes, cooled, spin-dried, and used dichloromethane: n-hexane=1:3 (v / v) as eluent on a silica gel column After separation, 450 mg (1.68 mmol) of the product 6-bromo-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline was obtained, with a yield of 84.0%.

[0070] NMR 1 H-NMR (CDCl 3 , 400MHz, ppm): δ1.17(s, 3H), 1.25(s, 3H), 1.30(d, 3H,), 1.47(dd, 1H), 1.75(dd, 1H), 2.75-2.80(m, 4H), 6.40 (d, 1H), 7.15 (dd, 1H), 7.17 (s, 1H).

[0071] (2) Synthesis of 6-(2-thienyl)-1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

[0072]

[0073] ...

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Abstract

The present invention relates to fine chemical and organic photoelectronic material technology, and is one kind of tetrahydro quinoline functional dye containing thiophene bridge chain. Structurally, the tetrahydro quinoline functional dye has 1, 2, 3, 4-tetrahydro quinoline and its derivative as electron donor, thiophene structure units in different number for regulating absorption spectrum and fluorescent emitting spectrum as bridge chain and different connected electron attracting group. Owing to the tetrahydro quinoline as chromophore with excellent electron donoring capacity, the thiophene with high electron cloud density, unique optical property and good electron transmitting capacity and the different connected electron attracting group, the functional dye has high light, heat and chemical stability and excellent photoelectronic property and may be used as photosensitive dye for solar cell and photoluminescent or electrochemoluminescent detection reagent.

Description

technical field [0001] The invention relates to a class of functional dyes in which 1,2,3,4-tetrahydroquinoline and its derivatives are used as electron donors, thiophene is used as a bridge chain and connected with different electron-withdrawing groups, and the compound is used in dye-sensitized nanocrystals Solar cells, photoluminescence or electrochemiluminescence are used in fluorescence detection and electroluminescence devices, etc., have good application performance. Background technique [0002] The compound synthesized by the present invention is a class of multifunctional dyes containing a thiophene structure. Due to the interaction between the lone pair of electrons on the heteroatom-sulfur and the chromogenic conjugated system, the excited state of the molecule is more likely to undergo charge transfer, thus producing Unique photoelectrochemical properties. It has good application properties in dye-sensitized nano-crystal solar cells, photoluminescence or electr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00H01L31/04H01G9/20G01N21/75
CPCY02E10/50
Inventor 杨希川陈瑞奎田海宁孙立成
Owner DALIAN UNIV OF TECH
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