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Phenazine metal fullerene derivative, preparation method and controlling method of lifetime of excited state

A technology of metallofullerenes and derivatives, applied in chemical instruments and methods, luminescent materials, color/spectral characteristic measurement, etc., can solve problems such as unclear control methods, short lifetime of excited states, complex control methods, etc., to achieve extended Excited state lifetime, low cost, and strong operability

Inactive Publication Date: 2017-11-10
BEIJING FUNAKANG BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problems of short lifetime and poor stability of the excited state of existing metallofullerenes, and overcome the technical problems such as ambiguity, complicated regulation means, and poor sensitivity of the current excited state lifetime of metallofullerenes, the present invention provides phenazines Metallofullerene derivatives, which have novel structures and long-lived excited states, and provide the preparation method, excited state lifetime regulation method and testing method of the phenazine metallofullerene derivatives

Method used

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  • Phenazine metal fullerene derivative, preparation method and controlling method of lifetime of excited state
  • Phenazine metal fullerene derivative, preparation method and controlling method of lifetime of excited state
  • Phenazine metal fullerene derivative, preparation method and controlling method of lifetime of excited state

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Embodiment 1

[0064] Preparation method of aniline compound with electron-donating group

[0065] 1. the preparation method of the phenazine compound of formula (1a), reaction scheme is:

[0066]

[0067] Specific steps include:

[0068] (1) 8g (38mmol) of 5,10-dihydro-5,10-dimethylphenazine and 5.8g (37mmol) of anhydrous phosphorus oxychloride of formula (1c) were added in 13ml of anhydrous DMF , then add 115ml of 1,4-dioxane, stir at room temperature, the solution turns red and solidifies, then add 100ml of 20% anhydrous sodium acetate solution, stir overnight, then evaporate to dryness to obtain a solid;

[0069] (2) Extract the obtained solid with water and dichloromethane, dissolve the product in dichloromethane, and purify it with a silica gel column to obtain the product of formula (1a).

[0070] The proton nuclear magnetic resonance spectrum of formula (1a) product is: 1 H NMR (400MHz, CDCl 3 -d, 293K) = 3.03(s, 3H, N-CH 3 ), 3.08(s, 3H, N-CH3), 6.38(d, 1H), 6.41(dd, 1H), 6....

Embodiment 2

[0084] Metallofullerene Sc 2 C 2 @C 82 -C 2v preparation method

[0085] Among the classes of metallofullerenes, metallofullerenes Sc 2 C 2 @C 82 The yield is relatively high, the properties are excellent, the variety is rich, and the research is relatively mature. Meanwhile, the metallofullerene Sc 2 C 2 @C 82 There are three isomers, namely C s 、C 2v and C 3v The configuration of different isomers has different excited state properties. for Sc 2 C 2 @C 82 -C 2v Bulk, under the condition of visible light excitation, electrons transition from the ground state to the excited state, effective intersystem crossing occurs, and a long-lived triplet state relaxation process is obtained, but the further application of the excited state on the order of nanoseconds (ns) is still restricted. Therefore, this application chooses metal fullerene Sc 2 C 2 @C 82 -C 2v As a starting material, it is conceived that through the regulation of external modification groups, a ...

Embodiment 3

[0092] Preparation method of phenazine metal fullerene derivatives

[0093] 1. the preparation method of the phenazine metallofullerene of formula (1), step comprises:

[0094]

[0095] (1) Take 0.91×10 3 nmol (ie 1 mg) of Sc 2 C 2 @C 82 -C 2v The solid sample was dissolved in toluene, and then 0.97×10 3 nmol (ie 0.1mg) of N-ethylglycine and 1.35×10 3 nmol (ie 0.6 mg) of compound 1a was filled with argon as a protective gas, and subjected to cycloaddition reaction, and reacted at 120°C for 20 minutes under stirring conditions;

[0096] (2) After the reactant was cooled for half an hour, the solution was evaporated to dryness, the product was dissolved in toluene, and then separated and purified by high performance liquid chromatography. The separation and purification steps were: use Buckyprep column (20 × 250mm, Cosmosil) to separate, In the experiment, toluene was used as the mobile phase, the flow rate of toluene was 12ml / min, the sample concentration was 1mg / ml, ...

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Abstract

The invention discloses a phenazine metal fullerene derivative, a preparation method and a controlling method of the lifetime of the excited state. The metal fullerene derivative is obtained by modifying a phenazine compound with electron donating characteristics on the surface of metal fullerene through an addition reaction. The lifetime of the excited state of the metal fullerene can be controlled through the method. The dynamical properties of the excited state of the phenazine metal fullerene derivative are characteristized by using femtosecond transient absorption spectra, and then the lifetime changes of the excited state are compared through data calculation and fitting. The phenazine metal fullerene derivative is novel in structure and has the advantages that the lifetime of the excited state is long and the characteristics of the excited state of the metal fullerene can be simply, efficiently and sensitively controlled. The phenazine metal fullerene derivative can be used in the optical physics and photochemistry processes, the problems that existing metal fullerene is short in lifetime of the excited state, undefined in controlling mode, complex in controlling means and poor in sensitivity are solved.

Description

technical field [0001] The invention relates to the field of metallofullerene materials, in particular to a phenazine metallofullerene derivative with a long excited state lifetime, a preparation method thereof, a method for regulating the excited state lifetime, and a testing method. Background technique [0002] Molecules with long-lived excited states can ensure efficient energy transfer and can participate in various photophysical and photochemical reactions. They are important in photoluminescence, phosphorescent bioimaging or molecular sensing, photodynamic therapy, and photocatalytic organic reactions. Applications. [0003] Traditional triplet photosensitizers are mainly some transition metal complexes. The disadvantages are relatively weak absorption in the visible light region, short lifetime of triplet excited states, high cost and few types. Organic triplet photosensitizers make up for some of the above shortcomings of transition metal complexes. They are a clas...

Claims

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Application Information

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IPC IPC(8): C07D403/04C07D403/10C09K11/06G01N21/31
CPCC07D403/04C07D403/10C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/31
Inventor 王春儒吴波
Owner BEIJING FUNAKANG BIOTECH CO LTD
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