CN116478126A - Preparation and application of strong A-D-A type organic micromolecular photosensitizer - Google Patents

Preparation and application of strong A-D-A type organic micromolecular photosensitizer Download PDF

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CN116478126A
CN116478126A CN202310292719.6A CN202310292719A CN116478126A CN 116478126 A CN116478126 A CN 116478126A CN 202310292719 A CN202310292719 A CN 202310292719A CN 116478126 A CN116478126 A CN 116478126A
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strong
photosensitizer
aie
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CN116478126B (en
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甄士杰
徐哲
李美静
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Guilin University of Technology
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Abstract

The invention belongs to the field of biomedical materials, and discloses preparation and application of a strong A-D-A type organic micromolecular photosensitizer. The invention is based on a receptor-donor-receptor configuration, having the structure shown below:wherein: ar is aromatic heterocycle and its derivative, X is hydrogen element or fluorine element or chlorine element. The invention is constructed by introducing groups such as strong electron-withdrawing cyano indenone, derivative and the like at two ends of donor triphenylamine or tetraphenyl ethylene and derivativeThe strong receptor-donor-receptor and the strong charge transfer state inhibit the intermolecular pi-pi stacking effect of molecules in an aggregation state, so that the AIE characteristic of the material is endowed. In addition, heavy atoms such as fluorine atoms or chlorine atoms are introduced, so that the energy gap crossing of the excited singlet state to the triplet state is promoted to realize efficient active oxygen generation. Based on the high-efficiency fluorescence quantum efficiency and ROS production capability, the material provided by the invention has a good application prospect in fluorescence imaging-mediated tumor photodynamic therapy.

Description

Preparation and application of strong A-D-A type organic micromolecular photosensitizer
Technical Field
The invention belongs to the field of biomedical materials, and particularly relates to preparation and application of an A-D-A type organic micromolecular photosensitizer.
Background
The traditional photosensitizers mostly have planar structures and relatively poor water solubility, and are easy to cause dense pi-pi accumulation among molecules to cause excited state molecules to return to a ground state in a non-radiative transition mode such as conversion and the like, and the aggregated state not only can cause fluorescence quenching of the photosensitizers, but also can greatly reduce the photosensitizing efficiency of the photosensitizers. The discovery of the AIE phenomenon solves these problems well, and these AIE molecules not only have strong fluorescence in the aggregated state, but also have good photosensitizing efficiency. According to perturbation theory, spin-orbit coupling (SOC) is enhanced or photosensitizer singlet state is reduced (S 1 ) To a singlet state (T 1 ) Energy gap difference (ΔE) ST ) Can promote the singlet state (S 1 ) To a singlet state (T 1 ) Inter-system cross-over (ISC) to enhance the photosensitizing efficiency of the photosensitizer. Spin-orbit coupling is a function of electron spin and orbit magnetic quantum number, and the stronger the nuclear electropositivity, namely the heavier the atoms, the stronger the coupling effect of electron spin and orbit magnetic quantum number, so that connecting the photosensitizer with heavy atoms is the most direct way of promoting intersystem crossing and improving the photosensitizer efficiency. S is S 1 And T 1 The energy difference of (2) is due to S only 1 The mutual exclusion of two valence electrons with opposite spin directions leads to the energy of the valence electrons being higher than T 1 The mutual exclusion of electrons and the distance between two valence electrons form a negative correlation, S 1 Separation of HOMO and LUMO in the process can effectively reduce S 1 To T 1 Energy gap difference (ΔE) ST ). The electron-withdrawing group is added into the molecular structure of the photosensitizer to promote the separation of HOMO and LUMO of the photosensitizer, thereby reducing the singlet S 1 To triplet state T 1 Is a bandgap difference of (2).
Disclosure of Invention
Aiming at the problems, the AIE material with high near infrared luminous efficiency, adjustable absorption and emission spectrum and good light stability is designed and synthesized, and the interference of self-absorption and autofluorescence of biological tissues is overcome. The preparation of the near infrared luminescent AIE material is realized by utilizing mechanisms such as enhancing conjugated chain length, intramolecular charge transfer and the like based on the cyano-indenone skeleton. Meanwhile, the photodynamic efficiency is improved by reducing the singlet state and triplet state energy level difference and other methods, and near-infrared AIE materials with high luminous efficiency and high photodynamic activity are screened out.
In order to achieve the above purpose, the present invention provides the following technical solutions: the preparation method and application of the strong A-D-A type organic micromolecular photosensitizer comprise the following steps:
in nitrogen atmosphere, aldehyde group-containing strong electron donor compound and cyano-indidone are mixed in the molar ratio of 1:3
Adding the mixture into a reactor, adding chloroform as a solvent and a catalyst pyridine, stirring the mixture by using a magnetic stirring device to dissolve the mixture, heating the mixture to 80 ℃ for reaction for 3 hours, decompressing and evaporating the solvent after the reaction is finished to obtain a crude product, and purifying the crude product by column chromatography to obtain the target compound.
The structure is I
Wherein x=fluorine element, chlorine element;
ar=an electron donating group of an aromatic ring derivative, and may be any of the following groups.
The invention has the beneficial effects that:
1. the invention synthesizes a new photosensitizer material system with AIE performance to overcome the problem of the decrease of tumor treatment effect caused by the fluorescence aggregation quenching effect and tumor hypoxia of the existing photosensitizer.
2. The near infrared photosensitizer with AIE property provided by the invention has stronger total active oxygen generating capacity than commercial photosensitizer chlorin (Ce 6).
3. The near infrared photosensitizer with AIE property provided by the invention has the advantages of few synthesis steps, simple method and easily available raw materials.
4. The near infrared photosensitizer with AIE property provided by the invention can have good fluorescence imaging effect on in-vitro cells and living tumors; even under the condition of hypoxia, the composition can still have good killing performance on cancer cells; but also has high-efficiency cure to the living tumor of the mice.
Drawings
FIG. 1 is a normalized absorption spectrum of TPAPT-4F and 2TPAPT-4F in THF;
FIG. 2 is a graph showing the emission spectra of the obtained materials TPAPT-4F and 2TPAPT-4F in THF
FIG. 3 shows the total active oxygen generating capacity of TPAPT-4F and 2TPAPT-4F, and photosensitizer Ce 6.
FIG. 4A and FIG. 4C are graphs showing fluorescence spectra under different water contents, and the fluorescence intensities of TPAPT-4F and 2TPAPT-4F are significantly increased after gradually adding water to THF solution, and FIG. 4B and FIG. 4D are I/I of TPAPT-4F and 2TPAPT-4F 0 And water content of the solvent mixture.
FIG. 5 is a mass spectrum of photosensitizer TPAPT-4F
FIG. 6 is a mass spectrum of photosensitizer 2TPAPT-4F
Detailed Description
The following technical solutions in the embodiments of the present invention will be clearly and completely described with reference to the accompanying drawings, so that those skilled in the art can better understand the advantages and features of the present invention, and thus the protection scope of the present invention is more clearly defined. The described embodiments of the present invention are intended to be only a few, but not all embodiments of the present invention, and all other embodiments that may be made by one of ordinary skill in the art without inventive faculty are intended to be within the scope of the present invention.
Example 1:
preparation of photosensitizer TPAPT-4F:
the synthetic route of the photosensitizer TPAPT-4F is as follows:
dibromotriphenylamine (0.4 g,0.99 mmol) (1), 5-aldehyde-2-thiopheneboronic acid0.38 g,2.4 mmol), palladium acetate (0.012 g,0.05 mmol), X-Phos (0.04 g,0.08 mmol), and potassium phosphate (1.72 g,7.9 mmol) were added to a mixed solvent of 20: 20 mL tetrahydrofuran and water 1:1. After being evenly mixed and stirred, the mixture is heated to 90 ℃ in the atmosphere of nitrogen o C, reaction 12 h, after cooling to room temperature, the mixture was filtered to remove insoluble impurities. The mixture was then poured into water and extracted three times with dichloromethane. The combined organic layers were washed successively with saturated sodium bicarbonate and water, and then dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography. Yellow solid (2) was obtained in 45.7% yield (357 mg). Weighing 0.2 g product and 5, 6-difluoro-3- (dicyanomethylene) indigonone (0.226 g,0.98 mmol), adding a few drops of pyridine as a catalyst, reacting at 70 ℃ for 4 h, cooling to room temperature, evaporating the solvent under reduced pressure, adding proper chloroform for dissolution, adding a large amount of methanol for separating out solid, and filtering to obtain dark black solid (0.2 g) with the yield of 93.8%.
The structural characterization data of the resulting product are shown below:
1 H NMR (400 MHz, C 6 D 6 ) δ 7.35 (s, 1H), 6.96 (s, 1H), 5.32 (s, 1H), 2.23 (d, J = 20.4 Hz, 4H), 1.87 – 1.54 (m, 4H), 1.37 (s, 6H), 0.87 (d, J = 6.5 Hz, 1H), 0.35 (d, J = 42.8 Hz, 5H).
example 2:
preparation of photosensitizer 2TPAPT-4F
The synthesis route of the photosensitizer 2TPAPT-4F is as follows:
4-Bromotrianiline (3.24 g,10 mmol) iodine (2.53 g,10 mmol) periodic acid (0.05 g,0.2 mmol) was dissolved in 50 mL absolute ethanol and heated to 80℃to react 4. 4 h, cooled to room temperature, the mixture was filtered and the product (2) was used directly in the next reaction. The product of the previous step (2.33 g,3.8 mmol), diphenylamine (1.71 g,10 mmol), cuprous iodide (0.046 g,0.2 mmol), 1.10-phenanthroline (0.043 g,0.2 mmol) and potassium hydroxide (1.71 g,30 mmol) were weighed and reacted in toluene solution at 120℃of 50 mL for 36 h. After cooling to room temperature, the mixture was filtered to remove insoluble impurities. Purifying by column chromatography to obtain 1.2 g target product (3). The above product (0.6 g,0.97 mmol), 5-aldehyde-2-thiopheneboronic acid (0.34 g,2.2 mmol), tetrakis (triphenylphosphine) palladium (0.11 g,0.097 mmol), potassium carbonate (0.5 g,3.64 mmol) were weighed out, 15 mL THF was added with 15 mL water, reacted under nitrogen atmosphere for 24 h, cooled to room temperature, and the mixture was filtered to remove insoluble impurities. Purification by column chromatography gave 0.5. 0.5 g target product (4) in 53% yield. 0.2. 0.2 g product and 5, 6-difluoro-3- (dicyanomethylene) indidone (0.18 g,0.79 mmol) were weighed, a few drops of pyridine was added as a catalyst, reacted at 70 ℃ for 4 h, cooled to room temperature, the solvent was evaporated under reduced pressure, the appropriate chloroform was added for dissolution, a large amount of methanol was added for precipitation of solid, and filtration gave a dark black solid (0.2 g) yield of 78.9%.
The structural characterization data of the resulting product are shown below:
1 H NMR (400 MHz, CD 2 Cl 2 ) δ 5.10 (d, J = 22.3 Hz, 1H), 2.04 (s, 3H), 1.67 (s, 3H), 1.53 (s, 13H), 1.26 (s, 8H), 0.87 (d, J = 4.1 Hz, 4H).
example 3:
absorption Spectrometry characterization of type A-D-A photosensitizers (TPAPT-4F and 2 TPAPT-4F)
FIG. 1 is a graph showing absorption spectra of TPAPT-4F and 2TPAPT-4F in THF based on the materials obtained in examples 1 and 2, wherein the maximum absorption spectrum of TPAPT-4F in THF solution is 616nm, and the maximum absorption wavelength of 2TPAPT-4F is 640 nm, which shows that the absorption spectrum is obviously red shifted by enhancing the electron donating ability of electron donating groups, promoting charge transfer in excited state molecules.
Example 4:
characterization of the emission spectra of type A-D-A photosensitizers (TPAPT-4F and 2 TPAPT-4F)
FIG. 2 is a graph of the maximum emission spectra of TPAPT-4F in THF and of the materials TPAPT-4F and 2TPAPT-4F obtained based on examples 1 and 2 in THF solution at 910 nm, and 2TPAPT-4F at 977 nm, indicating that the strong electron withdrawing effect of fluorine can impart ionic character to the C-F bond, which makes the C-F bond highly polarized, enhances electrostatic interactions between adjacent molecules, and promotes a red shift in emission wavelength.
Example 5:
ROS-forming ability of A-D-A type photosensitizers
FIG. 3 is a graph comparing the total active oxygen generating capacity of TPAPT-4F and 2TPAPT-4F, and photosensitizer Ce 6. The active oxygen probe DCFH, after binding to active oxygen, will generate green fluorescence at 522 nm. The time division concentration was 10. Mu.M in the test, and the optical density was 0.3W/cm by irradiation with a 660 nm laser -2 . The results show that the TPAPT-4F and 2TPAPT-4F molecules can generate higher fluorescence enhancement factors compared with Ce6, which indicates that the TPAPT-4F and 2TPAPT-4F molecules have stronger ROS generating capacity.
Example 6
FIG. 4A and FIG. 4C are graphs showing fluorescence spectra under different water contents, and after gradually adding water to THF solution, the fluorescence intensities of TPAPT-4F and TPAPT-4F are significantly increased, and FIG. 4B and FIG. 4D are I/I of TPAPT-4F and TPAPT-4F 0 Plot of water content of solvent mixture PL emissions of TPAPT-4F and TPAPT-4F were quenched before the critical point (0% water fraction). After the critical point, the fluorescence intensity increased with the addition of water, indicating its aggregation-induced emission characteristics.

Claims (5)

1. A strong A-D-A organic small molecule photosensitizer is characterized in that:wherein x=hydrogen, fluorine, chlorine; ar=an electron donating group of an aromatic ring derivative, and may be any of the following groups. />
2. The a-D-a type organic small molecule photosensitizer of claim 1, characterized in that: the AIE nano drug-carrying system is prepared by wrapping near infrared AIE materials, anti-tumor drugs, drug-resistant inhibitors and the like by amphiphilic polymers, and has the advantages of high fluorescence imaging capability, biocompatibility, fluorescence brightness and strong bleaching resistance.
3. The a-D-a type organic small molecule photosensitizer of claim 1, characterized in that: the AIE nano drug-carrying system is responsible for anti-tumor drugs and drug-resistant inhibitors and can be controllably released in the acidic environment of tumors, and the tumor is killed by using imaging-guided photodynamic therapy and photothermal therapy, so that the multi-mode combined treatment effect is achieved.
4. The a-D-a type organic small molecule photosensitizer of claim 1, characterized in that: based on a cyano-indenone skeleton, the preparation of the near infrared luminescent AIE material is realized by utilizing mechanisms of enhancing conjugated chain length, intramolecular charge transfer and the like.
5. The a-D-a type organic small molecule photosensitizer of claim 1, characterized in that: based on triphenylamine and tetraphenyl ethylene derivatives, the red shift of the luminescence wavelength is realized through a strong charge transfer state between the donor and the acceptor, so that the near infrared luminescent AIE material is obtained, and a near infrared AIE material system is enriched.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108299408A (en) * 2018-01-23 2018-07-20 西安近代化学研究所 Condensed ring A-D-A type conjugated molecules based on carbazole and preparation method thereof
CN113861392A (en) * 2021-10-13 2021-12-31 福州大学 Fluorenyl cyano indanone non-conjugated polymer receptor and preparation method thereof
WO2022024799A1 (en) * 2020-07-31 2022-02-03 ソニーグループ株式会社 Photoelectric conversion element and imaging device
WO2022129137A1 (en) * 2020-12-15 2022-06-23 Cambridge Display Technology Ltd. Compound

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108299408A (en) * 2018-01-23 2018-07-20 西安近代化学研究所 Condensed ring A-D-A type conjugated molecules based on carbazole and preparation method thereof
WO2022024799A1 (en) * 2020-07-31 2022-02-03 ソニーグループ株式会社 Photoelectric conversion element and imaging device
WO2022129137A1 (en) * 2020-12-15 2022-06-23 Cambridge Display Technology Ltd. Compound
CN113861392A (en) * 2021-10-13 2021-12-31 福州大学 Fluorenyl cyano indanone non-conjugated polymer receptor and preparation method thereof

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