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Fluoroborate pyrrole photosensitizer and synthetic method thereof

A technology of boron pyrrole photosensitizer and boron fluoride dipyrrole, which is applied in the field of new boron pyrrole photosensitizer and its synthesis, can solve the problems of high price and high cost, and achieve the effect of high yield

Inactive Publication Date: 2014-12-17
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, transition metal complexes are mostly used as photosensitizers, which are expensive and costly

Method used

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  • Fluoroborate pyrrole photosensitizer and synthetic method thereof
  • Fluoroborate pyrrole photosensitizer and synthetic method thereof
  • Fluoroborate pyrrole photosensitizer and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Microwave heating synthesis method of β-position iodoboron fluoride dipyrrole 3,5-position phenenyl derivatives

[0049] Dissolve β-iodoboron fluoride dipyrrole (50mg, 0.09mmol) and benzaldehyde (38mg, 0.36mmol) in 5ml N'N-dimethylformamide, glacial acetic acid (3 drops), piperidine (3 drop) was quickly added dropwise into the reaction solution, microwaved at 150°C for 15 minutes under an argon atmosphere, the product was washed with water to remove the solvent, filtered with suction, the filter cake was dissolved in dichloromethane, and the solvent was evaporated under reduced pressure to obtain a crude product. Purify by column chromatography (developer: dichloromethane) to obtain dark purple powder (40mg, 0.054mmol, 60%). 1 H NMR (400MHz, CDCl 3 ):δ=8.18-8.14(d,J=16.0Hz,2H),7.73(s,1H),7.69-7.66(m,5H),7.55-7.52(m,3H),7.44-7.41(m,4H ),7.37-7.33(d,J=16.0Hz,2H),7.31-7.29(m,2H),1.46ppm(s,6H).MALDI-HRMS calcd[C 33 h 25 BF 2 N 2 I 2 ] + m / z752.0168, found...

Embodiment 2

[0050] Example 2: Microwave heating synthesis method of β-position iodoboron fluoride dipyrrole 3,5-position p-cyanophenenyl derivatives

[0051] Dissolve β-iodoboron fluoride dipyrrole (50mg, 0.09mmol) and p-cyanobenzaldehyde (47mg, 0.36mmol) in 5ml N'N-dimethylformamide, glacial acetic acid (3 drops), piperazine Pyridine (3 drops) was quickly added dropwise to the reaction solution, microwaved at 150°C for 15 minutes under an argon atmosphere, the product was washed with water to remove the solvent, filtered with suction, the filter cake was dissolved in dichloromethane, and the solvent was evaporated under reduced pressure to obtain the crude product . Purify by column chromatography (developing solvent: dichloromethane) to give dark purple powder (36mg, 0.045mmol, 50%). 1 H NMR (400MHz, CDCl 3 ):δ=8.17-8.14(d,J=12.0Hz,1H),8.03-8.01(d,J=8.0Hz,1H),7.88-7.86(d,J=8.0Hz,1H),7.79(s, 1H),7.75-7.73(m,7H),7.60-7.59(d,J=4.0Hz,2H),7.56-7.54(m,2H),7.33-7.31(d,J=8.0Hz,2H),1.50 (s,6...

Embodiment 3

[0052] Example 3: Microwave heating synthesis method of β-position iodoboron fluoride dipyrrole 3,5-position p-nitrophenenyl derivatives

[0053] Dissolve β-iodoboronium fluoride dipyrrole (50mg, 0.09mmol) and p-nitrobenzaldehyde (54mg, 0.36mmol) in 5ml N'N-dimethylformamide, glacial acetic acid (3 drops), piperazine Pyridine (3 drops) was quickly added dropwise to the reaction solution, microwaved at 150°C for 15 minutes under an argon atmosphere, the product was washed with water to remove the solvent, filtered with suction, the filter cake was dissolved in dichloromethane, and the solvent was evaporated under reduced pressure to obtain the crude product . Purify by column chromatography (developing solvent: dichloromethane) to obtain dark purple powder (38mg, 0.045mmol, 50%). 1 H NMR (400MHz, CDCl 3 ):δ=8.14-8.10(d,J=16Hz,4H),7.56-7.53(d,J=12Hz,4H),7.30-7.28(m,3H),7.21-7.18(d,J=12Hz,2H ),7.14-7.11(m,4H),1.88(s,6H).MALDI-HRMS calcd[C 33 h 23 BF 2 N 4 I 2 o 4 ] + m / ...

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Abstract

The invention relates to a fluoroborate pyrrole photosensitizer and a synthetic method thereof as well as an application of the fluoroborate pyrrole photosensitizer in photocatalytic aromatization of 1,4-dihydropyridine. The general formula of the fluoroborate pyrrole photosensitizer is as shown in specification, wherein R is -Cn, -N(CH2CH3)2 or -NO2. According to the application of the fluoroborate pyrrole photosensitizer in photocatalytic aromatization of 1,4-dihydropyridine, the photocatalytic yield is above 94%.

Description

technical field [0001] The invention relates to a novel boropyrrole photosensitizer, a synthesis method thereof, and an application of the boropyrrole photosensitizer in photocatalytic aromatization of 1,4-dihydropyridine. Background technique [0002] Fluoropyrrole compound (BODIPY, usually called boron fluoride dipyrrole, boron difluoride complex dipyrromethene) is a conjugated planar structure compound formed by a boron nitrogen six-membered heterocycle sandwiched between two pyrrole rings. The two fluorine atoms attached to the boron atom flank the core plane. Fluoropyrrole compounds have multiple active sites, and their photochemical and photophysical properties can be effectively regulated through the introduction of functional groups. Fluoropyrrole and its derivatives are widely used in organic functional materials, bioluminescent analysis, photocatalysis and other fields because of their high fluorescence quantum yield, stable spectral properties, high photostabilit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J31/02C07D213/133
Inventor 吴文婷耿颖吴明铂郑经堂王瑞琴战力英张金强
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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