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Aniline Metal Fullerene Derivatives, Preparation Methods and Controlling Method of Excited State Lifetime

A technology of metallofullerenes and derivatives, applied in organic chemistry, color/spectral characteristic measurement, etc., can solve the problems of unclear control methods, short excited state life, and complicated control methods, and achieve long excited state life and low cost. Inexpensive, highly operable effect

Active Publication Date: 2019-09-10
赤峰福纳康生物技术有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 current technical problems such as ambiguity, complex regulation methods, and poor sensitivity of the current excited state lifetime of metallofullerenes, the present invention provides aniline metal The fullerene derivative has a novel structure and a long-lived excited state, and provides a preparation method, a method for regulating the lifetime of the excited state, and a testing method for the aniline metal fullerene derivative

Method used

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  • Aniline Metal Fullerene Derivatives, Preparation Methods and Controlling Method of Excited State Lifetime
  • Aniline Metal Fullerene Derivatives, Preparation Methods and Controlling Method of Excited State Lifetime
  • Aniline Metal Fullerene Derivatives, Preparation Methods and Controlling Method of Excited State Lifetime

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Embodiment 1

[0060] Preparation method of aniline compound with electron-donating group

[0061] 1. the preparation method of the aniline compound of formula (1a), reaction route is:

[0062]

[0063] Specific steps include:

[0064] (1) 1.42mmol (ie 387.66mg) of aldehyde triphenylamine of formula (1c) and 1.56mmol (ie 480mg) of formula (1d) of phosphate were mixed, then dissolved in 30ml of anhydrous tetrahydrofuran, and then 1.7 mmol (i.e. 191.2 mg) of potassium tert-butoxide, stirred and refluxed overnight, then cooled to room temperature, added water, the mixture was extracted with dichloromethane, the extracted product was dried with anhydrous sodium sulfate, the solvent was evaporated, and then filtered on a silica gel column Carry out purification, obtain the product of formula (1b);

[0065] (2) the product of formula (1b) of 1mmol (i.e. 426mg) and the p-formyl phenylboronic acid of 1.2mmol (i.e. 141.6mg) are dissolved in the water of 20ml ethanol and 15ml, then add the lead a...

Embodiment 2

[0083] Metallofullerene Sc 2 C 2 @C 82 -C S preparation method

[0084] ScNi used 2 Alloys were purchased from Beijing Institute of Nonferrous Metals.

[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 configuration, the excited state properties of different isomers are different, for Sc 2 C 2 @C 82 -C S and Sc 2 C 2 @C 82 -C 3V Under the condition of 530nm visible light excitation, the electronic dynamics curves of the excited state are all double-exponential relaxation processes. After analysis, there is no intersystem crossing to the triplet state, and Sc 2 C 2 @C 82 -C 2V Then there is a long-lived triplet relaxation process. Therefore, this application chooses metal fullerene Sc 2 C 2 @C 82 -C SAs ...

Embodiment 3

[0092] Preparation method of aniline metal fullerene derivatives

[0093] 1. the preparation method of the aniline metallofullerene of formula (1), the steps comprise:

[0094]

[0095] (1) Take 0.91×10 3 nmol (ie 1 mg) of Sc 2 C 2 @C 82 -C S 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, 1...

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Abstract

The invention discloses an aniline metal fullerene derivative and a preparation method thereof and a regulation method for the lifetime of an excited-state aniline metallofullerene derivative. The preparation method of the aniline metallofullerene derivative comprises the steps of in the presence of an amino acid, conducting an addition reaction, modifying the surface of metallofullerene with an aniline compound having an electron-donating property, and then obtaining the aniline metallofullerene derivative. The lifetime of the excited-state aniline metallofullerene derivative can be regulated through the preparation method. The kinetic properties of the excited-state aniline metallofullerene derivative are characterized by using femtosecond transient absorption spectra, and then changes of the lifetime of the excited-state aniline metallofullerene derivative are compared through data calculation and fitting. The aniline metallofullerene derivative is novel in structure, and the lifetime of the excited-state aniline metallofullerene derivative can reach the nanosecond order or the microsecond order, is long in lifetime and good in stability, and can be used in photophysical and photochemical processes; the problems that existing excited-state metallofullerene is short in lifetime, uncertain in regulation mode, complex in regulation way and poor in sensitivity are solved.

Description

technical field [0001] The invention relates to the field of metallofullerene materials, in particular to an aniline metallofullerene derivative with a long-lived excited state, a preparation method thereof, a method for regulating and testing the lifetime of the excited state. 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. application. [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 class of mol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/70G01N21/31
Inventor 王春儒吴波
Owner 赤峰福纳康生物技术有限公司
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