Ligand compound and functionalized metal-organic framework compound prepared from ligand compound, and preparation methods and applications thereof

A technology of ligand compounds and organic frameworks, applied in the field of functionalized metal-organic framework compounds and their preparation, can solve the problems of accelerating the intersystem crossing process, and achieve wide application value, high fluorescence quantum yield, and large emission intensity Effect

Active Publication Date: 2020-05-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The metal atoms in metal-organic frameworks have heavy atom effect, which greatly accelerates the intersystem crossing process and has a positive impact on phosphorescence and afterglow properties. It is expected to obtain ideal long-lasting materials. There are still very few reports

Method used

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  • Ligand compound and functionalized metal-organic framework compound prepared from ligand compound, and preparation methods and applications thereof
  • Ligand compound and functionalized metal-organic framework compound prepared from ligand compound, and preparation methods and applications thereof
  • Ligand compound and functionalized metal-organic framework compound prepared from ligand compound, and preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1 Preparation of functionalized metal-organic framework compound LIFM-ZCY-1

[0063] A functional metal-organic framework compound LIFM-ZCY-1, composed of 9-(4-(2,6-bis(4-(1H-tetrazol-5-yl)phenyl)pyridin-4-yl)benzene base)-9H-carbazole as a ligand, and chromium chloride dihydrate self-assembles.

[0064] The specific preparation process is:

[0065] Wherein the preparation process of 9-(4-(2,6-bis(4-(1H-tetrazol-5-yl)phenyl)pyridin-4-yl)phenyl)-9H-carbazole is:

[0066] S1. Preparation of intermediate product 4-(carbazol-9-yl)benzaldehyde (intermediate 1):

[0067] Carbazole (2.0g, 12mmol), 4-bromobenzaldehyde (2.5g, 13.5mmol), potassium carbonate (4.15 g, 30mmol), palladium acetate (0.2g, 1.0mmol), and tri-tert-butylphosphine (0.3 mL) of the mixture was dissolved in 20 mL of anhydrous toluene under a nitrogen atmosphere and refluxed for 48 hours. After the reaction, cool to room temperature, filter, and take the filtrate. The filtrate was extracted with wa...

Embodiment 2

[0075] Example 2 Determination of the crystal structure of the functionalized metal-organic framework compound LIFM-ZCY-1

[0076] with copper target Single crystal X-ray diffraction data of LIFM-ZCY-1 were collected at 50kV and 0.80mA on the Rigaku-Oxford Supernova X-ray Diffractometer system.

[0077] The structure was solved using the direct method and refined using the full matrix least squares method using the SHELXL-2014 program package. All hydrogen atoms were obtained by the theoretical hydrogenation method and refined along the anisotropic direction, using the isor command to fix the frame. The relevant crystallographic data of LIFM-ZCY-1 are shown in Table 1, and the topological structure is shown in figure 2 .

[0078] Table 1 shows the crystallographic data of the metal-organic framework complex LIFM-ZCY-1

[0079]

[0080] in, figure 2 The crystal structure diagram of LIFM-ZCY-1, a) the asymmetric unit structure of LIFM-ZCY-1; b) the one-dimensional cha...

Embodiment 3

[0081] Example 3 Measurement of Fluorescent Properties of LIFM-ZCY-1

[0082] The solid powder of LIFM-ZCY-1 exhibits blue fluorescence under excitation light with a wavelength of 365nm, the maximum emission peak is at around 460nm, and the maximum excitation peak is at around 370nm, as shown in image 3 shown.

[0083] Meanwhile, LIFM-ZCY-1 showed a thermochromic effect, such as Figure 4 shown. When the temperature gradually increased from 300K to 460K, a new peak around 560nm appeared behind the original fluorescence peak around 460nm. In addition, the position of this peak will redshift with the increase of temperature. When the temperature exceeds 460K, the new peak at around 600nm will no longer redshift. The emission color of LIFM-ZCY-1 also changed from blue at 300K to orange-red at 460K with the temperature rising, and the CIE coordinates changed from (0.21, 0.19) to (0.54, 0.42). After LIFM-ZCY-1 is heated and returns to room temperature, the sample still maintai...

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Abstract

The invention discloses a ligand compound and a functionalized metal-organic framework compound prepared from the ligand compound, and preparation methods and applications thereof. The structure of the ligand compound is represented by formula (I), the ligand compound is used as a ligand, the ligand compound and cadmium chloride are self-assembled to form the functionalized metal-organic frameworkcompound, and the functionalized metal-organic framework compound has high fluorescence quantum yield and long room-temperature phosphorescence lifetime, and has the advantages of high emission intensity and stable luminescence property; and under the vacuum condition, after an excitation light source is turned off, long-time continuous light emitting still exists. LIFM-ZCY-1 does not contain mercury, is nontoxic and non-volatile, is easy to recycle and has environmental friendliness; and the LIFM-ZCY-1 can be used for counterfeiting prevention through room-temperature phosphorescence characteristics, shows optical properties negatively related to the oxygen content, can be prepared into a light-emitting device, an anti-counterfeiting material and / or an oxygen sensor for application, andhas wide application value.

Description

technical field [0001] The present invention relates to the technical field of luminescent metal-organic framework materials, more specifically, to a ligand compound, namely 9-(4-(2,6-bis(4-(1H-tetrazol-5-yl)phenyl) )pyridin-4-yl)phenyl)-9H-carbazole, and a functionalized metal-organic framework compound prepared by self-assembly with cadmium chloride as a ligand, and a preparation method and application thereof. Background technique [0002] Long Persistent Luminescence (LPL) refers to the phenomenon that the material can continue to emit light for a period of time after the excitation light source is turned off. The history of afterglow can be traced back to the early 17th century, when an Italian shoemaker observed a strong afterglow from the mineral barite. The earliest materials to be researched and applied should be inorganic long-lasting materials. There are many natural ores in nature that have long-lasting luminescence characteristics. The well-known luminous pearl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C08G83/00C09K11/06G01N21/64
CPCC07D401/14C08G83/008C09K11/06C09K2211/188G01N21/64G01N21/6402
Inventor 潘梅朱诚逸王政扶鹏雁
Owner SUN YAT SEN UNIV
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