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Process for the preparation of benzohetero[1,3]diazole compounds disubstituted with heteroaryl groups

An azole compound and a disubstituted technology, applied in organic chemistry, photovoltaic power generation, etc., can solve the problems of long temperature and reaction time, long process time, high processing cost, etc., achieve short temperature and reaction time, short process time, low The effect of energy costs

Active Publication Date: 2014-08-20
ENI SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0033] - Use of a strong base [e.g. tert-butyl lithium (LiO-t-Bu)], therefore, difficulty in handling the base, greater potential for damage to the environment and operator's health, and higher disposal costs;
[0034] - relatively long temperatures and reaction times, therefore, energy costs, long process times that can lead to degradation of the products obtained

Method used

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  • Process for the preparation of benzohetero[1,3]diazole compounds disubstituted with heteroaryl groups
  • Process for the preparation of benzohetero[1,3]diazole compounds disubstituted with heteroaryl groups
  • Process for the preparation of benzohetero[1,3]diazole compounds disubstituted with heteroaryl groups

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0094] Preparation of 4,7-di-2-thienyl-2,1,3-benzothiadiazoles of formula (a)

[0095]

[0096] 4,7-dibromo-2,1,3-benzothiadiazole (0.294g, 1.0mmol), potassium acetate (0.295g, 3.0mmol), N,N-dimethylacetamide (5ml ), thiophene (0.842g, 10mmol) and palladium(II) acetate [Pd(OAc) 2 ] (1.2 mg, 0.005 mmol) was charged to a 10 ml Pyrex glass reactor fitted with a screw cap.

[0097] The reactor was preheated to 130°C in an oil bath and stirred vigorously for 4 hours. After cooling to room temperature (25°C), the reaction mixture was put into a saturated solution of sodium chloride (25ml) and extracted with ethyl acetate (3x25ml). The organic base obtained was dried over anhydrous sodium sulfate and evaporated. The obtained residue (brown solid) was purified by flash chromatography on silica gel using a mixture of n-heptane / ethyl acetate (1 / 1, v / v) as eluent to obtain 240 mg of pure 4,7-di-2-thienyl-2,1,3-benzothiadiazole (yield 80%).

[0098] The 4,7-di-2-thienyl-2,1,3-be...

example 2

[0101] Preparation of 4,7-bis-(5'-acetylthienyl)-2,1,3-benzothiadiazole having formula (b)

[0102]

[0103] 4,7-dibromo-2,1,3-benzothiadiazole (0.294g, 1.0mmol), potassium acetate (0.295g, 3.0mmol), N,N-dimethylacetamide (5ml ), 1-(thiophen-2-yl)ethanone (0.631g, 5mmol) and palladium(II) acetate [Pd(OAc) 2 ] (1.2 mg, 0.005 mmol) was charged to a 10 ml Pyrex glass reactor fitted with a screw cap.

[0104] The reactor was preheated to 120°C in an oil bath and stirred vigorously for 18 hours. Subsequent work-up as described in Example 1 afforded 339 mg of pure 4,7-bis-(5'-acetylthienyl)-2,1,3-benzothiadiazole as a red solid (88% yield) .

[0105] The 4,7-bis-(5'-acetylthienyl)-2,1,3-benzothiadiazole is passed 1 H-NMR (400MHz, CDCl 3 ), the following spectra were obtained: δ=8.13(d, J=4.0Hz, 2H), 7.96(s, 2H), 7.76(d, J=4.0Hz, 2H), 2.62(s, 6H).

[0106] The 4,7-bis-(5'-acetylthienyl)-2,1,3-benzothiadiazole was also characterized by MS mass analysis to obtain the followi...

example 3

[0108] Preparation of 4,7-bis-(5'-hexyl-2,2'-dithienyl)-2,1,3-benzothiadiazole having formula (c)

[0109]

[0110] 4,7-dibromo-2,1,3-benzothiadiazole (0.294g, 1.0mmol), potassium acetate (0.295g, 3.0mmol), N,N-dimethylacetamide (5ml), 5-hexyl-2,2'-dithiophene (1.252g, 5mmol) and palladium(II) acetate [Pd(OAc) 2 ] (1.2 mg, 0.005 mmol) was charged to a 10 ml Pyrex glass reactor fitted with a screw cap.

[0111] The reactor was preheated to 10°C in an oil bath and stirred vigorously for 18 hours. Subsequent work-up as described in Example 1 afforded 512 mg of pure 4,7-bis-(5'-hexyl-2,2'-bithienyl)-2,1,3-benzothiadiazole as a red solid (Yield 81%).

[0112] The 4,7-bis-(5'-hexyl-2,2'-dithienyl)-2,1,3-benzothiadiazole is passed 1 H-NMR (400MHz, CDCl 3 ) characterization, the following spectra were obtained: δ=8.03(d, J=4.0Hz, 2H), 7.83(s, 2H), 7.19(d, J=4.0Hz, 2H), 7.11(d, J=3.6Hz, 2H ), 6.73(d, J=3.6Hz, 2H), 2.82(t, J=7.6Hz, 4H), 1.73-1.69(m, 4H), 1.42-1.39(m, 4H), 1.3...

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Abstract

Process for the preparation of a benzohetero [1, 3] diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero [1, 3] diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero [1, 3] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero [1, 3] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero [1, 3] diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.

Description

technical field [0001] The present invention relates to a process for the preparation of benzohetero[1,3]oxadiazole compounds disubstituted with heteroaryl groups. [0002] More specifically, the present invention relates to a process for the preparation of benzohetero[1,3]oxadiazole compounds disubstituted with heteroaryl groups, the process comprising making at least one disubstituted benzohetero[1, 3] Reaction of an oxadiazole compound with at least one heteroaryl compound. [0003] The heteroaryl group disubstituted benzohetero[1,3]oxadiazole compounds can be advantageously used in the construction of luminescent solar concentrators (LSCs). Furthermore, the heteroaryl group disubstituted benzohetero[1,3]oxadiazole compounds can be advantageously used to construct photovoltaic devices on rigid and flexible substrates, such as, for example, photovoltaic cells, photovoltaic modules, solar cells, Solar modules. The heteroaryl group disubstituted benzohetero[1,3]oxadiazole c...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D519/00C07D413/14C07D417/14
CPCC07D409/14C07D413/14C07D495/04C07D519/00C07D417/14
Inventor 吉尔里安纳·施姆普纳加布里尔·比安奇
Owner ENI SPA
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