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1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane and preparation method therefor

A technology based on pyridyl vinyl and pyridyl, which is applied in 1 field to achieve the effects of mild reaction conditions, simple and easy-to-operate process, and excellent fluorescence performance

Active Publication Date: 2019-05-03
GUANGXI UNIV FOR NATITIES
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There is no relevant literature report on 1,2-bis(pyridyl)-3,4-bis(4-pyridylvinyl-3-fluorobenzene)cyclobutane

Method used

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  • 1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane and preparation method therefor
  • 1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane and preparation method therefor
  • 1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1) Take 30.2 mg (0.1 mmol) of 3,5-bis(2-pyridine vinyl) fluorobenzene, Cd(NO 3 ) 2 4H 2 O30.8mg (0.1mmol) and p-chlorobenzoic acid 15.6mg (0.1mmol) join in the rigid glass tube of one end closure, add 4mL water in the glass tube, adjust the pH= of the system with nitric acid (concentration is 65%) 3. Melt and seal the other end of the glass tube, and then place the glass tube at 100°C for 30 hours of constant temperature reaction. After the reaction is completed, lower it to room temperature (the cooling rate is 5°C / h), take it out, and you can see that the inner wall of the glass tube A pale yellow crystal was precipitated, which was intermediate 1 (120.8 mg, yield 78%).

[0026] The characterization of intermediate 1 is as follows:

[0027] IR:v(KBr) / cm -1 3071(w), 1614(s), 1585(s), 1532(s), 1392(s), 1269(m), 1215(m), 1165(w), 1089(w), 1014(m), 969(m), 877(m), 845(m), 770(m), 663(m), 534(m), 439(m);

[0028] 1 H NMR (400MHz, d 6 -DMSO, 298K, TMS): δ=8.62 (d, ...

Embodiment 2

[0060] 1) Take 30.2 mg (0.1 mmol) of 3,5-bis(2-pyridine vinyl) fluorobenzene, Cd(NO 3 ) 2 4H 2 O30.8mg (0.1mmol) and p-chlorobenzoic acid 15.6mg (0.1mmol) join in the rigid glass tube of one end closure, add 2mL water in the glass tube, adjust the pH of the system with nitric acid (concentration is 69%)= 4. Melt and seal the other end of the glass tube, and then place the glass tube at 80°C for 36 hours of constant temperature reaction. After the reaction is completed, lower it to room temperature (the cooling rate is 10°C / h), take it out, and you can see the inner wall of the glass tube Bright yellow crystals were precipitated, which were intermediate 1 (108.4 mg, yield 70%);

[0061] 2) Take the obtained single crystal of Intermediate 1, grind it to 200-300 meshes, and then irradiate the ground powder under an ultraviolet lamp with an emission wavelength of 254nm for 4 hours (it can be observed that the color of the powder becomes darker during the irradiation process) , ...

Embodiment 3

[0065] 1) Take 30.2 mg (0.1 mmol) of 3,5-bis(2-pyridine vinyl) fluorobenzene, Cd(NO 3 ) 2 4H 2 O30.8mg (0.1mmol) and p-chlorobenzoic acid 15.6mg (0.1mmol) join in the rigid glass tube of one end closure, add 5mL water in the glass tube, adjust the pH= of system with hydrochloric acid (concentration is 36%) 1. Melt and seal the other end of the glass tube, then place the glass tube at 120°C for a constant temperature reaction for 12 hours. After the reaction is completed, lower it to room temperature (the cooling rate is 8°C / h), take it out, and you can see the inner wall of the glass tube Bright yellow crystals were precipitated, which were intermediate 1 (92.9 mg, yield 60%);

[0066] 2) Take the obtained single crystal of intermediate 1, grind it to 200-300 mesh, and then irradiate the ground powder under an ultraviolet lamp with an emission wavelength of 350nm for 3 hours (it can be observed that the color of the powder becomes darker during the irradiation process) , to...

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Abstract

The invention discloses 1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane and a preparation method therefor. The preparation method for the 1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane comprises the following steps: 1) weighing and dissolving 3,5-di(2-pyridylvinyl)fluorobenzene, cadmium nitrate tetrahydrate and parachlorobenzoic-acid in a solvent, adjusting a pH value of the obtained solution to be not greater than 6, placing the obtained mixed solution in a vessel, carrying out sealing, and carrying out a reaction under the condition of heating, so as to obtain an intermediate 1; 2) irradiating the intermediate 1 with ultraviolet light with the wavelength of 254nm to 450nm, so as to obtain an intermediate 2; and 3) soaking the intermediate 2 in an acidic solution with a pH value not greater than 4, carrying out filtering, collecting filter liquor, adjusting a pH value of the filter liquor to be alkaline, precipitating solids, and collecting the solids, thereby obtaining the 1,2-di(pyridyl)-3,4-di(4-pyridylvinyl-3-fluorobenzene)cyclobutane. According to the method disclosed by the invention, the process is simple and easy in operation, and the yield is high; and chemical properties of the target product and all the intermediates are stable.

Description

technical field [0001] The invention relates to an organic ligand containing multiple pyridine groups, in particular to 1,2-bis(pyridyl)-3,4-bis(4-pyridylvinyl-3-fluorobenzene)cyclobutane and a preparation method thereof . Background technique [0002] It is very important to use [2+2] photochemical reaction to synthesize four-membered rings and their derivatives, but it is difficult to realize their efficient photochemical transformation. Recent studies have shown that the efficiency of such [2+2] photochemical reactions involving the synthesis of four-membered cyclobutanes can be significantly enhanced in the solid phase, especially under crystalline conditions, with the help of template molecules. The solid-phase [2+2] photochemical reaction has high regioselectivity and high stereoselectivity, does not require organic solvents, and has a high conversion rate, so it is in line with the concept of green chemistry. [0003] The study of Schmidt's criteria on the solid-sta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26C09K11/06
Inventor 胡飞龙王梦凡高渝康米艳黄钦尹显洪
Owner GUANGXI UNIV FOR NATITIES
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