Preparation method and application of aggregation-induced emission platinum complex

A technology of aggregation-induced luminescence and platinum complexes, applied in the field of phosphorescent materials

Pending Publication Date: 2022-03-01
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, AIE platinum complexes with 2,2'-bipyridine as an auxiliary ligand have not been reported

Method used

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  • Preparation method and application of aggregation-induced emission platinum complex
  • Preparation method and application of aggregation-induced emission platinum complex
  • Preparation method and application of aggregation-induced emission platinum complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The synthesis of embodiment 1 compound 1

[0023] (1) Synthesis of cyclometal ligand intermediates:

[0024] In air, add 1.0 mmol of 2-bromo-5-fluoropyridine, 3-bromophenylboronic acid (1.5 equiv.), potassium carbonate (2.0 equiv.), palladium acetate (1.5% equiv.) to the round bottom flask successively, Then add 8 mL of ethanol-water mixed solution with a volume ratio of 3:1, and carry out Suzuki coupling reaction at 80°C with magnetic stirring, and track the reaction process by thin-layer chromatography. Methane was extracted three times, the organic phases were combined, concentrated under reduced pressure, and separated by column chromatography to obtain a cyclometal ligand intermediate with a yield of 63%.

[0025] (2) Synthesis of cyclometal ligands:

[0026] In air, add 1.0 mmol of cyclometal ligand intermediate, phenylboronic acid (1.5 equiv.), sodium carbonate (2.0 equiv.), tetrakis(triphenylphosphine) palladium (3.0% equiv.) , then add 8mL of tetrahydrofuran...

Embodiment 2

[0029] The synthesis of embodiment 2 compound 2

[0030]Example 2 has the same preparation method as Example 1, except that the pyridine derivative used in the synthesis of the ring metal ligand intermediate in Example 2 is 2-bromopyridine, and the synthesis of the ring metal ligand uses arylboronic acid The compound is 4-fluorophenylboronic acid.

[0031] 2 The yield is 55%, and the structural characterization data are as follows: 1 H NMR (400MHz, DMSO-d 6 )δ9.21(d, J=5.8Hz, 1H), 8.91(d, J=5.6Hz, 1H), 8.75(d, J=6.0Hz, 1H), 8.51(m, 2H), 8.32(t, J=7.9Hz, 1H), 8.24(d, J=8.0Hz, 2H), 8.11(t, J=7.8Hz, 1H), 7.93(s, 1H), 7.84–7.76(m, 3H), 7.72( t, J = 6.8Hz, 1H), 7.35 (p, J = 8.7, 7.2Hz, 4H), 7.24 (d, J = 8.0Hz, 1H). HRMS (LTQ Orbitrap XL, m / z) calculated value: C 27 h 19 FN 3 Pt[M-PF 6 ] + 599.1211, measured value: 599.1193.

Embodiment 3

[0032] The synthesis of embodiment 3 compound 3

[0033] Example 3 has the same preparation method as Example 1, except that the pyridine derivative used in the synthesis of the ring metal ligand intermediate in Example 3 is 2-bromopyridine, and the synthesis of the ring metal ligand uses arylboronic acid The compound is 3-fluorophenylboronic acid.

[0034] 3 The yield is 76%, and the structural characterization data are as follows: 1 H NMR (400MHz, DMSO-d 6 )δ9.22(d, J=6.3Hz, 1H), 8.93(d, J=5.6Hz, 1H), 8.78(d, J=6.0Hz, 1H), 8.60–8.46(m, 2H), 8.29( dt,J=16.0,9.8Hz,3H),8.14(t,J=7.9Hz,1H),8.02(s,1H),7.82(t,J=6.3Hz,1H),7.73(d,J=6.6 Hz,1H),7.64(m,1H),7.56(t,J=7.3Hz,1H),7.49–7.36(m,2H),7.25(q,J=8.8Hz,3H).HRMS(LTQ Orbitrap XL ,m / z) calculated value: C 27 h 19 FN 3 Pt[M-PF 6 ] + 599.1211, measured value: 599.1190.

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Abstract

The invention discloses a preparation method and application of aggregation-induced emission platinum complexes, and belongs to the field of phosphorescent materials. Five platinum complexes are prepared by taking a 2-phenylpyridine derivative as a cyclometalated ligand and 2, 2 '-dipyridyl as an auxiliary ligand, and the platinum complexes prepared by the invention have remarkable aggregation-induced emission property and have important application value in the field of phosphorescent materials.

Description

technical field [0001] The invention relates to a preparation method and application of a class of cyclometal platinum complexes with aggregation-induced luminescent properties, belonging to the field of phosphorescent materials. Background technique [0002] Traditional fluorescent molecules usually have strong fluorescence in dilute solutions, and the fluorescence will be weakened or even quenched at high concentrations. In 2001, Tang Benzhong et al. discovered that a class of small organic molecules had no fluorescence in dilute solution, but showed bright fluorescence emission in the aggregated state (Chem. Commun., 2001, 18, 1740-1741). They described this abnormal phenomenon as It is called aggregation-induced emission (Aggregation-Induced Emission, abbreviated as AIE). The discovery of aggregation-induced luminescence provides an effective way to solve the major scientific problem of aggregation-induced luminescence quenching, and greatly promotes the development of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC07F15/0086C09K11/06C09K2211/185
Inventor 刘春张鑫艺王俊安
Owner DALIAN UNIV OF TECH
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