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CN-122010864-A - Alkyl chain length adjustable phenoxazine room temperature phosphorescent material, preparation and application thereof

CN122010864ACN 122010864 ACN122010864 ACN 122010864ACN-122010864-A

Abstract

The invention discloses a phenoxazine room temperature phosphorescent material POZn with adjustable alkyl chain length, which is prepared by dissolving phenoxazine, C n H2 n+1 Br and sodium hydride in an organic solvent under the atmosphere of inert gas, reacting for 15-20 min under ice bath conditions, then heating to reflux temperature of 40-60 ℃ for 36-48 h, obtaining a compound POZn after the mixture is subjected to post treatment, introducing alkyl chains with different carbon chain lengths into the skeleton of a phosphorescent unit, regulating room temperature phosphorescent performance of the material by regulating steric hindrance and molecular stacking modes, and under the condition of changing the upper carbon chain length of the phenoxazine, the strategy is to deeply study the structure-activity relationship between different carbon chain lengths and phosphorescent performance and promote the development of the organic room temperature phosphorescent material.

Inventors

  • OUYANG MI
  • MA PEIDONG
  • SUN QI
  • Zhou Lvting
  • Xing Qirui
  • ZHANG CHENG

Assignees

  • 浙江工业大学

Dates

Publication Date
20260512
Application Date
20260319

Claims (10)

  1. 1. An alkyl chain length adjustable phenoxazine room temperature phosphorescent material POZn as shown in formula I: I wherein n is 2, 4, 6, 10 or 12.
  2. 2. The preparation method of the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn shown in the formula I in the claim 1 is characterized by comprising the steps of dissolving phenoxazine, C n H 2n+1 Br and sodium hydride in an organic solvent under the atmosphere of inert gas, reacting for 15-20 min under the ice bath condition, then heating to 40-60 ℃ for reacting for 36-48 hours, and carrying out post-treatment on the obtained mixture to obtain the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn, wherein the mass ratio of the phenoxazine, C n H 2n+1 Br and sodium hydride is 1:1-2:2-3; I In the formula I, n is 2, 4, 6, 10 or 12, and n in the C n H 2n+1 Br is the same as n in the formula I.
  3. 3. The preparation method of the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn is characterized in that the post-treatment is that the obtained mixture is subjected to water quenching, dichloromethane extraction, water washing, drying, concentration and column chromatography purification in sequence, and ethyl acetate and petroleum ether are used as eluent for elution, so that the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn is obtained.
  4. 4. The method for preparing the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn according to claim 2, wherein the organic solvent is anhydrous tetrahydrofuran.
  5. 5. The method for preparing the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn according to claim 2, wherein the volume of the organic solvent is 10-15ml/g based on the mass of the phenoxazine.
  6. 6. The use of the alkyl chain length adjustable phenoxazine type room temperature phosphorescent material POZn in the preparation of host-guest doped room temperature phosphorescent film according to claim 1.
  7. 7. The use according to claim 6, characterized in that the application method is as follows: Dissolving the alkyl chain length adjustable phenoxazine room temperature phosphorescent material POZn in ethyl acetate to prepare mother liquor with the concentration of 0.01-0.05mmol/mL, mixing the mother liquor with bisphenol A diglycidyl ether and 1, 3-propylene diamine, stirring, coating the mixed liquor on a substrate, solidifying and separating the substrate to obtain the host guest doped room temperature phosphorescent film, wherein the coating amount of the mixed liquor on the substrate is 1-1.5 mL/cm 2 , the mass ratio of the bisphenol A diglycidyl ether to the 1, 3-propylene diamine is 4-5:1, and the mass ratio of the mother liquor to the total mass ratio of the mother liquor, the bisphenol A diglycidyl ether and the 1, 3-propylene diamine is 1:2-5.
  8. 8. The use of claim 7, wherein the substrate is a glass sheet or a quartz plate.
  9. 9. The use according to claim 7, wherein the mother liquor concentration is 0.02 mmol/mL.
  10. 10. The use according to claim 7, wherein the ratio of the mass of said mother liquor to the total mass of said mother liquor, bisphenol a diglycidyl ether and 1, 3-propanediamine is 1:4.5.

Description

Alkyl chain length adjustable phenoxazine room temperature phosphorescent material, preparation and application thereof Technical Field The invention belongs to the technical field of organic luminescent materials, and particularly relates to a phenoxazine long-life organic room-temperature phosphorescent material POZn with an adjustable alkyl chain length, a preparation method and application thereof. Background Long afterglow luminescence refers to a photoluminescence phenomenon that can maintain luminescence for more than 100 milliseconds after the excitation light source is removed, also called continuous luminescence. The long afterglow luminescence is an ideal signal light source, and can effectively eliminate the influence caused by common short-life background light, thereby greatly improving the signal-to-noise ratio. Materials with long afterglow luminescence property are also called noctilucent materials or light-accumulating luminescent materials, and the materials have wide application prospects in the fields of anti-counterfeiting, information encryption, optical recording, emergency lighting, traffic signs, biological imaging, photodynamic therapy and the like. At present, the long afterglow luminescent material mainly comprises inorganic materials such as inorganic compounds doped with lanthanide rare earth elements. The pure organic room temperature phosphorescent material does not contain heavy metals, can observe phosphorescence at room temperature, and has wide application prospect compared with inorganic materials due to the advantages of low price, safety, innocuity and the like. However, the organic long afterglow materials are still quite limited in variety because of late onset of development. Thus, the design of synthetic efficient organic long persistence materials remains one of the challenges in the field of photovoltaic materials. The alkyl chains with different carbon chain lengths are introduced, and the performance of the organic room-temperature phosphorescent material can be influenced by regulating and controlling the steric hindrance and molecular stacking mode. Different stacking modes and steric hindrance can be constructed by regulating the length of the alkyl chain, the spin orbit coupling effect of heavy atoms is avoided, the intermolecular effect and the rigid environment are changed, and the triplet state exciton behavior is indirectly regulated. Disclosure of Invention The invention aims to greatly prolong the phosphorescence life of the phenoxazine organic room temperature phosphorescence material containing alkyl chains with different lengths by introducing the alkyl chains with different carbon chain lengths into the phenoxazine, and simultaneously provides a new synthesis method and new application for the organic room temperature phosphorescence material. The invention provides a room temperature phosphorescent material POZn of an alkyl chain length adjustable phenoxazine as shown in a formula I: I wherein n is 2, 4, 6, 10 or 12. The preparation method comprises the steps of dissolving phenoxazine, C nH2n+1 Br and sodium hydride in an organic solvent in an inert gas atmosphere, reacting for 15-20 min under ice bath conditions, then heating to 40-60 ℃ for 36-48 h, and performing aftertreatment on the obtained mixture to obtain the alkyl chain length-adjustable phenoxazine room temperature phosphorescent material POZn, wherein the mass ratio of the phenoxazine, C nH2n+1 Br and sodium hydride is 1:1-2:2-3 (preferably 1:1.5:2.6); I In the formula I, n is 2, 4, 6, 10 or 12, and n in the C nH2n+1 Br is the same as n in the formula I. Further, the post-treatment comprises the steps of sequentially carrying out water quenching, dichloromethane extraction, water washing, drying, concentration and column chromatography purification on the obtained mixture, eluting by using ethyl acetate and petroleum ether (preferably with the volume ratio of 30:1) as eluent, and obtaining the alkyl chain length adjustable phenoxazine room temperature phosphorescent material POZn. Further, the organic solvent is anhydrous tetrahydrofuran. Further, the volume of the organic solvent is 10-15ml/g (preferably 12 ml/g) based on the mass of the phenoxazine. The invention also provides an application of the alkyl chain length adjustable phenoxazine room temperature phosphorescent material POZn in preparing a host-guest doped room temperature phosphorescent film. Further, the application method is as follows: Dissolving the alkyl chain length adjustable phenoxazine room temperature phosphorescent material POZn in ethyl acetate to prepare a mother solution with the concentration of 0.01-0.05mmol/mL (preferably 0.02: 0.02 mmol/mL), mixing the mother solution with bisphenol A diglycidyl ether and 1, 3-propanediamine, stirring, coating the mixed solution on a substrate, solidifying, and separating from the substrate to obtain the host-guest doped room temperature phosphorescent film, wherein the