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Compound based on chiral binaphthol-terpyridyl platinum and preparation method of compound

A technology of binaphthol and terpyridine, applied in the field of chiral fluorescent materials, can solve problems such as limited application, and achieve the effects of low synthesis cost, simple synthesis route and potential application value

Active Publication Date: 2020-01-07
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such complexes can only generate CPL signals in solution, which greatly limits their application in the field of solid-state circularly polarized luminescence.

Method used

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  • Compound based on chiral binaphthol-terpyridyl platinum and preparation method of compound
  • Compound based on chiral binaphthol-terpyridyl platinum and preparation method of compound
  • Compound based on chiral binaphthol-terpyridyl platinum and preparation method of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of compound BTPt-Cl:

[0040] Potassium chloroplatinite (100mg, 0.242mmol) was added to the reactor, dissolved in deionized water (12mL), and then compound BT (153mg, 0.242mmol) dissolved in acetonitrile (36mL) was added, heated to reflux for 24 hours to react A large amount of red suspended matter was generated in the container, and then the heating was stopped. After the reaction system was cooled to room temperature, the crude product was obtained by suction filtration, and then the compound BTPt-Cl was obtained by column chromatography with a developer of dichloromethane / methanol at a volume ratio of 15:1. (82 mg, 61% yield).

[0041] like figure 1 as shown, 1 H NMR (300MHz, DMSO-d 6 )δ / ppm=8.95(s,2H),8.78(dd,J=10.2,7.1Hz,4H),8.48(dd,J=16.1,8.4Hz,3H),8.19(t,J=8.0Hz,2H ), 8.03(d, J=7.8Hz, 1H), 7.89(t, J=6.5Hz, 2H), 7.72(d, J=9.2Hz, 1H), 7.57(t, J=7.4Hz, 1H), 7.39(dt,J=16.0,7.4Hz,3H),7.18–6.99(m,2H),3.83(s,3H),3.26(s,3H).

[0042] like figure 2 as sh...

Embodiment 2

[0048] Synthesis of compound BTPt-Cl:

[0049] Potassium chloroplatinite (301mg, 0.726mmol) was added to the reactor, dissolved in deionized water (18mL), and then compound BT (153mg, 0.242mmol) dissolved in acetonitrile (36mL) was added, heated to reflux for 48 hours to react A large amount of red suspended matter was generated in the container, and then the heating was stopped. After the reaction system was cooled to room temperature, the crude product was obtained by suction filtration, and then the compound BTPt-Cl was obtained by column chromatography with a developer of dichloromethane / methanol at a volume ratio of 15:1. .

[0050] Synthesis of compound BTPt-OTf:

[0051] Compound BTPt-Cl (80mg, 0.1mmol) and silver trifluoromethanesulfonate (26mg, 0.1mmol) were added in the reactor, heated to reflux in 5mL of methanol for 2 hours, the system gradually changed from orange-red to gray-green at the beginning, After stopping the reaction. After the system was cooled to ro...

Embodiment 3

[0053] Synthesis of compound BTPt-Cl:

[0054] Potassium chloroplatinite (100mg, 0.242mmol) was added to the reactor, dissolved in deionized water (12mL), then compound BT (153mg, 0.242mmol) dissolved in acetonitrile (60mL) was added, heated to reflux for 18 hours to react A large amount of red suspended matter was generated in the container, and then the heating was stopped. After the reaction system was cooled to room temperature, the crude product was obtained by suction filtration, and then the compound BTPt-Cl was obtained by column chromatography with a developer of dichloromethane / methanol at a volume ratio of 15:1. .

[0055] Synthesis of compound BTPt-OTf:

[0056] Compound BTPt-Cl (80mg, 0.1mmol) and silver trifluoromethanesulfonate (77mg, 0.3mmol) were added to the reactor, heated to reflux in 5mL of methanol for 1 hour, the system gradually changed from orange-red to gray-green at the beginning, After stopping the reaction. After the system was cooled to room te...

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Abstract

The invention discloses a compound based on chiral binaphthol-terpyridyl platinum and a preparation method of the compound. The preparation method comprises the steps: dissolving a compound BT in a first solvent and stirring to form a first solution; dissolving potassium chloroplatinite in a second solvent, and stirring to form a second solution; adding the second solution into the first solution,and carrying out heating reflux to obtain BTPt-Cl; dissolving silver trifluoromethanesulfonate and the BTPt-Cl in a third solvent, and carrying out heating reflux to obtain BTPt-OTf. The invention discloses the compound based on chiral binaphthol and terpyridyl platinum and a preparation method of the compound; the compound based on chiral binaphthol and terpyridyl platinum, having an aggregation-induced near-infrared circular polarization luminescence property and having a highest luminescence asymmetry factor up to 10<-1> is prepared through two-step synthesis. The method has the advantagesof low synthesis cost, simple synthesis route and easiness in product purification, and the synthesized target compound has the axial chiral structure of binaphthol and the fluorescence characteristic of terpyridyl platinum, and has the aggregation-induced luminescence property.

Description

technical field [0001] The invention relates to a chiral binaphthol-terpyridine platinum complex and a preparation method thereof, belonging to the technical field of chiral fluorescent materials. Background technique [0002] Circularly polarized luminescence is an optical phenomenon unique to some chiral luminescent substances. It can not only intuitively reflect the structural information of chiral luminescent molecules in the excited state, but also be used in the fields of biological detection, 3D display, information storage, and asymmetric photochemical synthesis. There is huge application value. Therefore, such materials have aroused extensive research interest. [0003] Early studies mainly focused on chiral metal complexes including rare earth metals and transition metals, through the combination of chiral ligands and metals, thereby changing the chiral environment of metal ions to regulate CPL signals. However, such complexes can only generate CPL signals in sol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC07F15/0093C09K11/06C09K2211/185C07B2200/07
Inventor 刘志鹏高婷婷姜志勇王小青
Owner NANJING FORESTRY UNIV
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