CN113880886B - Nickel metal complex and preparation method and application thereof - Google Patents
Nickel metal complex and preparation method and application thereof Download PDFInfo
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- CN113880886B CN113880886B CN202111196289.5A CN202111196289A CN113880886B CN 113880886 B CN113880886 B CN 113880886B CN 202111196289 A CN202111196289 A CN 202111196289A CN 113880886 B CN113880886 B CN 113880886B
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Abstract
The invention discloses a metallic nickel complex, a preparation method and application thereof. The method comprisesThe metallic nickel complex has a structure shown in the following formula I, wherein: r is R 1 Each occurrence is independently selected from C 1‑10 Alkyl, -C 1‑6 alkyl-C 6‑12 Aryl, C 6‑12 Aryl, -C 6‑12 aryl-C 1‑6 An alkyl group; p (P) 1 、P 2 Each occurrence is independently selected from H, halogen, C 1‑6 Alkyl, C 2‑6 Alkenyl, C 3‑20 Aryl, C 3‑20 Heteroaryl, and when P 1 、P 2 When neither is H or halogen, adjacent P 1 、P 2 Can be bonded into a ring; d is an electron donating group; a is an electron withdrawing group. The metal nickel complex has better fluorescence luminescence performance.
Description
Technical Field
The invention relates to the technical field of luminescence. More particularly, relates to a metallic nickel complex, a preparation method and application thereof.
Background
Photoluminescence refers to the absorption of an external light source by a compound such that energy-generating excited photons undergo a radiative transition back to the ground state, accompanied by fluorescence or phosphorescence. The heavy atom (e.g., palladium, platinum) effect can enhance the spin-orbit coupling constant, accelerate the intersystem crossing process, and cause the generated triplet exciton radiation to transition back to the ground state. However, nickel as the first transition metal has the weakest d-d Ligand Field (LF) splitting energy compared to palladium and platinum, noble metals. In the non-d 10 The presence of such thermally accessible lower d-d LF excited state electron configuration in the closed shell essentially quenches the luminescence excited state. This process is through thermal equilibrium or energy transfer from other near or higher energy excited states to the metal center LF state. Thus, nickel (II) complexes generally do not emit light. How to realize the luminescence of the metal nickel complex is a technical problem to be solved.
Disclosure of Invention
Based on the above problems, the invention provides a metal nickel complex, a preparation method and application thereof, so as to realize the luminescence of the metal nickel complex.
In a first aspect, the present invention provides a metallic nickel complex, which is characterized by having a structure represented by the following formula I:
wherein:
R 1 each occurrence is independently selected from C 1-10 Alkyl, -C 1-6 alkyl-C 6-12 Aryl, C 6-12 Aryl, -C 6-12 aryl-C 1-6 An alkyl group;
P 1 、P 2 each occurrence is independently selected from H, halogen, C 1-6 Alkyl, C 2-6 Alkenyl, C 3-20 Aryl, C 3-20 Heteroaryl, and when P 1 、P 2 When neither is H or halogen, adjacent P 1 、P 2 Can be bonded into a ring;
d is an electron donating group;
a is an electron withdrawing group.
Further, the C 1-10 The alkyl is selected from one of methyl, ethyl, propyl, isopropyl and n-butyl.
Further, the-C 1-6 alkyl-C 6-12 Aryl is selected from 1, 3-dimethylphenyl orWherein->The junction site is shown.
Further, the electron donating group is selected from carbazole derivatives, diphenylamine derivatives, phenoxazine derivatives, phenothiazine derivatives or acridine derivatives. Under the condition of keeping electron donating group D in the metal nickel complex, fluorescence enhancement can be realized by increasing the strong field ligand A, and the emission spectrum is red shifted along with the enhancement of the intensity of the strong field ligand. The strong field ligand can raise the metal d-d orbit to avoid the d-d deactivation of fluorescence, so that the luminous wavelength is enhanced and the emission spectrum shows red shift.
Further, the electron withdrawing group is selected from cyano, isothiocyanato, trifluoromethyl, trichloromethyl, nitro, halogen, trimethyl or methyl.
Further, the C 3-20 Aryl is preferably C 6-20 An aryl group; the C is 3-20 Heteroaryl is preferably C 6-20 Heteroaryl groups.
Further, the-C 1-6 alkyl-C 6-12 Aryl is preferably-C 1-3 alkyl-C 6-12 An aryl group; the-C 6-12 aryl-C 1-6 Alkyl is preferably-C 6-12 aryl-C 1-3 An alkyl group.
Further, the C 2-6 Alkenyl groups are selected from ethenyl, propenyl, and the like.
Further, the electron donating group is selected from the groups corresponding to a to g below:
wherein:
Q 1 、Q 2 the same or different, independently of one another, from H, methyl, ethyl, propyl or isopropyl;
the junction site is shown.
Further, the electron withdrawing group is selected from one of the following groups:
wherein, the liquid crystal display device comprises a liquid crystal display device,the junction site is shown.
Further, the metallic nickel complex is selected from one of the following formulas A1 to a 24:
in a second aspect, the present invention provides a method for preparing the above metal nickel complex, comprising the steps of:
1) Under nitrogen atmosphere, alkaline conditions and in the presence of solventReflux-reacting with electron donor group-containing compound to obtain +.>Wherein D is an electron donating group;
2) Under nitrogen atmosphere, alkaline conditions, catalyst and solventAnd->Reflux reaction to obtain->Wherein P is 1 、P 2 Each occurrence is independently selected from H, halogen, C 1-6 Alkyl, C 2-6 Alkenyl, C 3-20 Aryl, C 3-20 Heteroaryl, and when P 1 、P 2 When neither is H or halogen, adjacent P 1 、P 2 Can be bonded into a ring;
3) In a solvent andunder reflux conditions, willAnd R is R 1 -Cl reaction, get->Wherein R is 1 Each occurrence is independently selected from C 1-10 Alkyl, -C 1-6 alkyl-C 6-12 Aryl, C 6-12 Aryl, -C 6-12 aryl-C 1-6 An alkyl group;
4) Under the conditions of solvent and reflux, the liquid,reacting with anhydrous nickel chloride to obtain +.>
5) Under the condition of nitrogen atmosphere and super-dry solvent, the mixture is preparedAnd reacting with a compound containing an electron withdrawing group to obtain the metal nickel complex.
Further, in the step 1), in the alkaline condition, the alkaline source is potassium tert-butoxide; the solvent is N, N-dimethylformamide.
Further, in the step 2), in the alkaline condition, the alkaline source is potassium carbonate; the catalyst is copper oxide; the solvent is dimethyl sulfoxide.
Further, in step 3), the solvent is dichloromethane.
Further, in step 4), the solvent is N, N-dimethylformamide.
Further, in step 5), both the raw materials and the solvent are subjected to dry deoxygenation treatment.
Further, in step 5), the reaction is carried out in the presence of an acid-binding agent selected from organic or inorganic bases, for example in the presence of potassium carbonate.
In a third aspect, the present invention provides the use of a metallic nickel complex as described above in a photoluminescent material.
The beneficial effects of the invention are as follows:
in the structure of the metal nickel complex, nickel is bridged to an acceptor structure, so that a front line orbit (HOMO-LUMO energy level) is effectively separated, and a strong field ligand cyano group is introduced, so that the excited state is prevented from being deactivated through a d-d orbit of the metal nickel, and the L' LCT room-temperature fluorescence in a molecule induced by the ligand is realized. In addition, the metal nickel complex has a structure with only a small amount of accumulated products and a good luminous effect.
Drawings
The following describes the embodiments of the present invention in further detail with reference to the drawings.
FIG. 1 shows the emission spectrum of the organometallic complex A1 synthesized in example 1 (1.16x10 therein -3 mmol/L、6.09x10 -4 mmol/L、3.12x10 -4 mmol/L、1.58x10 -4 mmol/L and 7.95x10 -5 mmol/L represents the concentration of the dichloromethane solution of compound A1).
FIG. 2 shows the emission spectrum of the organometallic complex A1 synthesized in example 1 (in which air and argon represent the test sample conditions).
Fig. 3 shows a luminescence lifetime diagram of the organometallic complex A1 synthesized in example 1 in methylene chloride.
Fig. 4 shows a luminescence lifetime diagram of the organometallic complex A8 synthesized in example 1 in methylene chloride.
FIG. 5 shows the emission spectra of organometallic complexes A1 and A8 synthesized in example 1 in methylene chloride.
Detailed Description
In order to more clearly illustrate the present invention, the present invention will be further described with reference to preferred embodiments and the accompanying drawings. Like parts in the drawings are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and that this invention is not limited to the details given herein.
In embodiments of the present invention, the starting materials and reagents used in the following examples are commercially available, unless otherwise indicated, or may be prepared by known methods.
Example 1
First, n-butyl substituted nickel compound A8 was prepared:
the preparation process of A8 is as follows: 3, 6-Di-t-butylcarbazole (10 g), potassium t-butoxide (5.3 g) and N, N-dimethylformamide (100 mL) were stirred and mixed before adding to a 500mL round bottom flask. After stirring at room temperature for 1 hour, 3, 5-bromofluorobenzene (13 g) was added to a round bottom flask and reacted under argon atmosphere at 150℃for 24 hours. After cooling to room temperature, water was added to precipitate a precipitate, which was then filtered and recrystallized from methanol to give compound I-b as a white solid.
Compound I-b (10 g), benzimidazole (6 g), potassium carbonate (7 g), copper oxide (0.45 g) and dimethyl sulfoxide (100 mL) were mixed and refluxed overnight at 150 ℃. After the reaction was completed, water was added at room temperature, and the product was precipitated as a precipitate. The solid was filtered and collected, recrystallized from methanol to give compound I-c as an off-white solid.
To compound I-c (5 g) and iodobutane (15 mL) was added dichloromethane (40 mL) and stirred under reflux for 12h. And filtering the generated precipitate after the reaction is finished, and recrystallizing filter residues with dichloromethane to obtain a white solid compound I-d.
Compound I-d (1 g), nickel chloride (0.25 g), and sodium acetate (0.42 g) were dissolved in 30ml of N, N-dimethylformamide and reacted under an argon atmosphere at 160℃for 24 hours. After the reaction was completed, water was added at room temperature, and the product was precipitated as a precipitate. The solid was filtered and collected, and recrystallized from methanol to give compound A8 as a yellow solid. The specific synthetic route is shown in scheme a below.
Preparation of n-butyl substituted compounds A1 to A7:
the preparation process of the compound A1 comprises the following steps: compound A8 (0.5 g) and tetrabutylammonium cyanide (0.45 g) were dissolved in 50ml of methylene chloride and reacted at 60℃under reflux for 6h. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to obtain a red solid compound A1.
The preparation process of the compound A2 comprises the following steps: compound A8 (0.5 g) and sodium isothiocyanamide (0.3 g) were dissolved in 50ml of methylene chloride and reacted at 60℃under reflux for 4 hours. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to give compound A2 as a red solid.
The preparation process of the compound A3 comprises the following steps: compound A8 (0.5 g) and sodium nitrite (0.3 g) were dissolved in 50ml of methylene chloride and reacted at 60℃under reflux for 2 hours. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to obtain a red solid compound A3.
The preparation process of the compound A4 comprises the following steps: compound A8 (0.5 g) and trifluoromethyl silane (0.45 mL) were dissolved in 50mL of tetrahydrofuran and stirred at room temperature overnight. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to obtain a red solid compound A4.
The preparation process of the compound A5 comprises the following steps: compound A8 (0.5 g) and trichlorosilane (0.45 mL) were dissolved in 50mL of tetrahydrofuran and stirred overnight at room temperature. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to obtain a red solid compound A5.
The preparation process of the compound A6 comprises the following steps: compound A8 (0.5 g) and trimethylsilane (0.45 mL) were dissolved in 50mL of tetrahydrofuran and stirred overnight at room temperature. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to obtain a red solid compound A6.
The preparation process of the compound A7 comprises the following steps: a solution of compound A8 (0.5 g) and methyllithium in tetrahydrofuran (0.3 mL) was dissolved in 50mL of tetrahydrofuran and stirred at room temperature overnight. After the reaction, the liquid was filtered and collected, and after the liquid was spin-dried, it was recrystallized from methanol to obtain a red solid compound A7.
A1: 1 H NMR(400MHz,Chloroform-d)δ8.24(s,2H),7.75(s,2H),7.56(t,J＝9.5Hz,4H),7.46(t,J＝8.7Hz,8H),4.89–4.63(m,4H),2.07(t,J＝7.9Hz,4H),1.71–1.64(m,4H),1.53(d,J＝3.1Hz,18H),1.11(d,J＝7.3Hz,6H).
A2: 1 H NMR(400MHz,Chloroform-d)δ8.21(s,2H),7.71(d,J＝6.7Hz,2H),7.52(t,J＝10.1Hz,4H),7.42(t,J＝8.8Hz,8H),4.75(d,J＝39.6Hz,4H),2.16–1.93(m,4H),1.50(s,18H),1.30(d,J＝29.2Hz,6H).
A3: 1 H NMR(400MHz,Chloroform-d)δ8.19(s,2H),7.77(s,2H),7.46(t,J＝9.5Hz,4H),7.36(t,J＝8.7Hz,8H),4.79–4.65(m,4H),2.14(t,J＝7.9Hz,4H),1.71–1.64(m,4H),1.53(d,J＝3.1Hz,18H),1.11(d,J＝7.3Hz,6H).
A4: 1 H NMR(400MHz,Chloroform-d)δ8.33(s,2H),7.75(s,2H),7.42(t,J＝10.1Hz,4H),7.62(t,J＝8.9Hz,8H),4.75(d,J＝36.9Hz,4H),2.18–1.95(m,4H),1.49(s,18H),1.35(d,J＝29.9Hz,6H)
A5: 1 H NMR(400MHz,Chloroform-d)δ8.27(s,2H),7.71(s,2H),7.31(t,J＝11.9Hz,4H),7.31(t,J＝9.6Hz,8H),4.64(d,J＝39.1Hz,4H),2.14–1.90(m,4H),1.60(s,18H),1.34(d,J＝22.4Hz,6H)
A6: 1 H NMR(400MHz,Chloroform-d)δ8.20(s,2H),7.74–7.67(m,2H),7.55–7.47(m,4H),7.42(d,J＝7.0Hz,8H),4.89(t,J＝7.1Hz,4H),3.41(t,9H),2.15(s,4H),1.50(s,18H),1.26(t,J＝7.1Hz,4H),1.04(t,J＝7.3Hz,6H).
A7: 1 H NMR(400MHz,Chloroform-d)δ8.27(s,2H),7.79–7.85(m,2H),7.54–7.30(m,2H),7.50–7.41(m,2H),7.32(d,J＝6.9Hz,8H),4.51(t,J＝6.9Hz,4H),2.73(s,3H),2.11(s,4H),1.50(s,18H),1.21(t,J＝7.9Hz,4H),1.11(t,J＝7.9Hz,6H).
A8: 1 H NMR(400MHz,Chloroform-d)δ8.21(d,J＝1.9Hz,2H),7.72(d,J＝6.1Hz,2H),7.55–7.47(m,4H),7.46–7.32(m,8H),5.10(s,4H),2.05(d,J＝23.6Hz,4H),1.58(dd,J＝15.2,7.7Hz,4H),1.50(s,18H),1.04(t,J＝7.3Hz,6H).
Reference to the preparation of A8 also produced a16, the synthetic route of which is shown in scheme b:
reference to the preparation of A1 also produced A9, the synthetic route of which is shown in scheme c.
Reference to the preparation of A2 also produced A10, the synthetic route of which is shown in scheme c.
Reference to the preparation of A3 also produced A11, the synthetic route of which is shown in scheme c.
Reference to the preparation of A4 also produced A12, the synthetic route of which is shown in scheme c.
Reference to the preparation of A5 also produced A13, the synthetic route of which is shown in scheme c.
Reference to the preparation of A6 also produced A14, the synthetic route of which is shown in scheme c.
Reference to the preparation of A7 also produced A15, the synthetic route of which is shown in scheme c.
Reference to the preparation of A8 also produced a24, the synthetic route of which is shown in scheme d:
reference to the preparation of A1 also produced A17, the synthetic route of which is shown in scheme e.
Reference to the preparation of A2 also produced A18, the synthetic route of which is shown in scheme e.
Reference to the preparation of A3 also produced A19, the synthetic route of which is shown in scheme e.
Reference to the preparation of A4 also produced A20, the synthetic route of which is shown in scheme c.
Reference to the preparation of A5 also produced A21, the synthetic route of which is shown in scheme e.
Reference to the preparation of A6 also produced A22, the synthetic route of which is shown in scheme e.
Reference to the preparation of A7 also produced A23, the synthetic route of which is shown in scheme e.
Example 2
The emission spectra of the metal complexes A1 to a24 in methylene chloride solution were compared and the quantum yields are shown in table 1. Wherein, the steady-state emission spectrum of the metallic nickel compound in methylene dichloride solution is composed of a xenon lamp light source of a photophysical test platform model ELS-980 of Edinburgh company and an MCP-PMT detector, and the detector is tested in a range from 300nm to 900nm. The absolute quantum yield of the metallic nickel compound in methylene chloride solution was tested in a photoluminescence quantum yield spectrophotometer C11347 equipped with an integrating sphere. The lifetime of the metallic nickel compound in methylene chloride solution was measured by Edinburgh company model number ELS-980, the excitation light source was a laser, and the metallic nickel compound was obtained by fitting analysis by software F900.
It was found that the compounds A1 to A3 were red-shifted by 30 to 40nm than the compounds A4 to A8, and the quantum yield was improved by 5 times or more, and the lifetime was also increased. Because the A of the compound is selected from cyano, isothiocyanato and nitroso, the A is a strong field auxiliary ligand and has stronger electron withdrawing capability. The compounds A1-A3 realize the construction of a donor-acceptor structure, and meanwhile, the strong field auxiliary ligand A is used for chelating the nickel compound, so that the d-d orbit deactivation of an excited state through the metal center nickel is avoided, and LLCT luminescence is realized. The fluorescence of compounds A4-A7 is relatively weak, due to the absence of strong field ligands and electron withdrawing groups. The emission spectra of compounds A9 to a24 in methylene chloride solution also show similar phenomena. Compared with the compounds A1 and A9, the cyano group is the structure A, but the compound A9 of which the carbazole is selected as D has a more conjugated structure, and the compound A9 is obviously red-shifted. Compared with the compounds A9 and A16, the two compounds A are cyano groups, D is carbazole, and only P is changed 1 And P 2 Structure is as follows. We find that benzimidazole carbene is 33nm red shifted than imidazole carbene, because benzimidazole carbene is a conjugated structure, the d-d orbit of metallic nickel can be improved more effectively.
TABLE 1 photophysical data of organometallic complexes in dichloromethane solution
Example 3
The compound A1 prepared in example 1 realizes the construction of a donor-nickel-acceptor structure, and simultaneously uses a strong-field ligand CCC ligand and an auxiliary ligand cyano-chelated nickel compound, so as to avoid the deactivation of an excited state through a d-d orbit of metal center nickel, thereby realizing the L' LCT luminescence. The emission spectra of the metal complex A1 in methylene chloride at different concentrations are shown in FIG. 1, and fluorescence is quenched with increasing concentration. As shown in fig. 2, the luminescence intensity was hardly changed in an argon and nitrogen atmosphere, which indicates that the compound A1 is a fluorescent compound mainly emitting a ligand. FIGS. 3 and 4 are graphs showing luminescence lifetime of compounds A1, A8 in methylene chloride in sequence; FIG. 5 is a graph showing the emission spectra of compounds A1 and A8 in methylene chloride.
It should be understood that the foregoing examples of the present invention are provided merely for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention, and that various other changes and modifications may be made therein by one skilled in the art without departing from the spirit and scope of the present invention as defined by the appended claims.
Claims (2)
1. A metallic nickel complex, characterized in that the metallic nickel complex is selected from one of the following formulas A1-A3:
。
2. use of a metallic nickel complex as defined in claim 1 for the preparation of a photoluminescent material.
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