Fluoro-boron diisoindole compounds and preparation method thereof

A compound, the technology of isoindole, which is applied in the field of fluoroborate diisoindole compounds and their preparation, can solve the problems of affecting biological activity, lengthy synthetic route, and increased difficulty of compound synthesis, and achieve the increase of π-bond conjugation range , the effect of changing photochemical and physical properties

Inactive Publication Date: 2015-03-25
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the problem existing in the prior art is that in order to “red shift” the absorption and emission wavelengths of the existing fluoroboron dipyrrole compounds, it is generally necessary to introduce a conjugated group of a macromolecule into the parent molecule (if it is necessary to introduce multiple styrene group or phenylacetylene group, etc.), resulting in increased difficulty in the synthesis of such compounds (long synthetic route and low yield, etc.)
In addition, fluoroborate dipyrrole compounds with too large molecular weight will affect their absorption in the body, thereby affecting their biological activity

Method used

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  • Fluoro-boron diisoindole compounds and preparation method thereof
  • Fluoro-boron diisoindole compounds and preparation method thereof
  • Fluoro-boron diisoindole compounds and preparation method thereof

Examples

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preparation example Construction

[0025] The method for preparing the compound shown in formula I provided by the present invention specifically comprises the following steps:

[0026] (1) Synthesis of 4-substituted phenylhydrazine (compound shown in formula III)

[0027] Add 20~25mmol of ethyl 4-substituted benzoate (compound shown in formula II), 50~60mmol of hydrazine hydrate (N 2 h 4 ·H 2 O), add 50~60mL dehydrated alcohol simultaneously as solvent, stir, after 75~80 ℃ heat reflux 6~7h, remove solvent, have precipitation to separate out, filter, dry, obtain 4-substituted phenylhydrazine (formula III indicated compounds);

[0028] (2) Synthesis of N-[1-(aryl)ethylidene]aromatic hydrazide (compound shown in formula V)

[0029] Add 15~20mmol of 4-substituted benzohydrazide prepared in step (1), 18~20mmol of 4,5-substituted 2-hydroxyacetophenone (compound shown in formula IV) into the reaction bottle, and add 50~60mL of dehydrated ethanol, stirred, heated to reflux at 75-80°C for 48-50h, the solvent was r...

Embodiment 1

[0039] 1,1'-bis(4,4'-fluoro)phenyl-3,3'-fluoroborodiisoindolylidene (IA)

[0040]

[0041] (1) Synthesis of 4-fluorobenzoylhydrazide

[0042] Add 3.36g (20mmol) ethyl p-fluorobenzoate, 5.00g (50mmol) hydrazine hydrate (N2H4 H2O) and 50mL absolute ethanol to a 100mL reaction flask, stir, heat and reflux at 75-80°C for 6h, then distill off the ethanol, White needle-like crystals were precipitated, filtered, washed, and dried to obtain 2.78 g of 4-fluorobenzoic hydrazide, yield: 90.3%, melting point: 163°C.

[0043] (2) Synthesis of N-[1-(2-hydroxyphenyl)ethylidene]-4-fluorobenzohydrazide

[0044]Add 2.31g (15mmol) of 4-fluorobenzoic hydrazide, 2.44g (18mmol) of 2-hydroxyacetophenone, and 50mL of absolute ethanol into a 100mL reaction bottle, stir, heat and reflux at 75-80°C for 48 hours, and wait for the reaction After the end, a yellow solid precipitated, filtered, washed, and dried to obtain 3.35 g of N-[1-(2-hydroxyphenyl)ethylidene]-4-fluorobenzohydrazide, yield: 82.2%,...

Embodiment 2

[0054] 1,1'-bis(4,4'-chloro)phenyl-3,3'-fluoroborodiisoindolylidene (IB)

[0055]

[0056] Except that the ethyl p-fluorobenzoate in step (1) of Example 1 was replaced with ethyl p-chlorobenzoate, other conditions were the same as in Example 1 to obtain the title compound.

[0057] 1 H NMR (400MHz, CDCl 3 ),δ:7.84(d,2H,J=8.4Hz),7.77(s,1H),7.79(d,4H,J=8.4Hz),7.52 (d,2H,J=8.0Hz),7.48~7.39 (m,6H),7.20~7.20(m,2H).

[0058] HRESI-MS535.0726.([M+Na] + , calcd for C 29 h 17 BF 2 N 2 Cl 2 Na:535.0722).UV:λmax=648nm.Fluorescence:λem=673nm.

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Abstract

The invention relates to fluoro-boron diisoindole compounds and a preparation method thereof. Compared with the conventional fluoro-boron dipyrrole compounds, according to the fluoro-boron diisoindole compounds, pyrrole rings are directly replaced by isoindole rings, the conjugated range of pi bonds in a parent molecule is increased and thus the photochemical and physical properties of the compounds are changed, molecular absorption and emission wavelengths cause a 'red shift', the maximum ultraviolet absorption wavelength can reach 640nm-680nm and the maximum fluorescence emission wavelength is up to 670nm-713nm and the fluoro-boron diisoindole compounds are near-infrared fluorescent dyes.

Description

technical field [0001] The invention relates to a fluoroboron diisoindole compound with a novel structure and a preparation method thereof. Background technique [0002] The fluoroboron dipyrrole compound is a compound formed by fixing two pyrrole molecules on a plane with a boron bridge bond and a methine bridge bond, and its structure is shown in the following formula. [0003] [0004] This type of compound has a high molar absorptivity (usually ε>80000cm -1 m -1 ) and fluorescence quantum yield, and has good photostability, so it has been widely studied in the fields of fluorescent chemical sensors, solar cell photoreceptors, liquid crystal materials, and supramolecular polymers. Recently, there have been some reports that by modifying the structure of fluoroborate dipyrrole compounds, their optical properties are changed, making them suitable for the research of photosensitizers or fluorescent probes. [0005] O'shea et al. reported an azafluoroboropipyrrole co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B23/04C09K11/06
Inventor 杨晓霞陶晓春蔡良珍林智星蔺卉
Owner EAST CHINA UNIV OF SCI & TECH
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