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Borondifluoride complexes of curcominoid compounds, method of preparation and uses thereof

A compound, boron difluoride technology, applied in the field of boron difluoride complexes, to achieve the effects of enhanced optical properties, high optical brightness, and enhanced fluorescence quantum yield

Inactive Publication Date: 2018-08-21
UNIV DE PROVENCE D AIX MARSEILLE I +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

While such interactions can account for the emission that occurs in the NIR, they inherently induce efficient face-to-face quenching, thereby reducing the fluorescence quantum yield (Φ f ) to about 5% (A.D'Aléo, D.Gachet, V.Heresanu, M.Giorgi and F.Fages, Chem.Eur.J., 2012, 18, 12764-12772; G.Bai, C. Yu, C. Cheng, E. Hao, Y. Wei, X. Mu and L. Jiao, Org. Biomol. Chem., 2014, 12, 1618-1626)

Method used

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  • Borondifluoride complexes of curcominoid compounds, method of preparation and uses thereof
  • Borondifluoride complexes of curcominoid compounds, method of preparation and uses thereof
  • Borondifluoride complexes of curcominoid compounds, method of preparation and uses thereof

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Experimental program
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Embodiment 1

[0236] Embodiment 1: the synthesis of compound 4

[0237] The synthesis of compound 4 is described below. The two-photon excited fluorescence (TPEE) properties of 4 were characterized in solution. The preparation and fluorescence emission of organic nanoparticles obtained using 4 are also described. This allows to give an example of compounds as defined in the present invention having improved emission both in solution and in the solid state.

[0238]

[0239] The synthesis of compound 4 first requires the preparation of compound A. This intermediate was prepared by the Noevenger reaction using an excess of acetylacetone (acetylacetone / aldehyde 3:1) to provide compound A in a reasonable yield of 60% (G. Mann, L. Beyer and A. Arrieta, Z. Chem., 1987, 27, 172-173). Then, the reaction of two equivalents of A with 1,3,5-tris(n-octoxy)benzene afforded 4 in 34% yield.

[0240] Complexation with boron difluoride was carried out by reacting compound B with a slight excess of...

Embodiment 2

[0250] Example 2: Electrochemical, photophysical and solid-state optical properties of compound 4 and comparison with other compounds

[0251] Here the electrochemical and optical properties of four compounds in organic solvents are reported: borondifluoride complexes of three monocurcuminoids (named X, Y, and Z) and borondifluoride complexes of the biscurcuminoid system Compound complex compound 4 compared. The two-photon excited fluorescence properties (TPEF) of four compounds in solution were characterized.

[0252] The molecular structures of borodifluoride curcumin derivatives X, Y, and Z are shown below.

[0253]

[0254] 2.1 Comparison of electrochemical properties

[0255] Electrochemical properties of compounds X, Y, Z and 4 in the presence of 0.1M (n-Bu) 4 NPF 6 studied in dichloromethane (DCM) solution.

[0256] figure 1 The cyclic voltammetry curve (CV) is given in, and Table 1 lists the oxidation and reduction half-wave potential values ​​(E 1 / 2 , r...

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Abstract

The present invention relates to new borondifluoride complexes of curcuminoid compounds with an enhanced fluorescence quantum yield and emission, and their uses as fluorophore in various fields such as bioimaging, therapeutics, theranostics, display and telecommunication technologies, photovoltaics. The preparation of said compounds is also described.

Description

technical field [0001] The present invention relates to boron difluoride complexes of novel curcuminoids with enhanced fluorescence quantum yield and emission, and their applications in many fields such as bioimaging, therapy, theranostics, display and communication technologies, photovoltaics, etc. applications as fluorophores in various fields. The preparation of said compounds is also described. Background technique [0002] Compounds exhibiting high molar absorptivity, large two-photon absorption cross section, high luminescence quantum yield in solution and in the solid state, large Stokes shift, and high thermal and photochemical stability are represented as fluorescent reporters attractive candidates. In particular, there is great interest in the use of dyes emitting in the near-infrared (NIR, wavelengths greater than 700 nm according to the International Commission on Illumination) for cellular imaging using two-photon excitation in the NIR region, since both excit...

Claims

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Application Information

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IPC IPC(8): C07F5/02A61B5/00A61K49/00G01N31/00G01N21/00
CPCA61K49/0021C07F5/022G01N31/221G01N33/6896G01N2800/2821A61K49/0019G01N31/22G01N33/582
Inventor 埃莱娜·扎波罗夫弗雷德里克·法热安东尼·达里奥
Owner UNIV DE PROVENCE D AIX MARSEILLE I
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