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CN-117800874-B - Flexible crystal material of dibenzoacrylonitrile, preparation method and application thereof

CN117800874BCN 117800874 BCN117800874 BCN 117800874BCN-117800874-B

Abstract

The invention discloses a flexible crystal material of dibenzoacrylonitrile, a preparation method and application thereof, and relates to the field of organic photoelectric functional materials, wherein the basic structure of the organic fluorescent material takes the dibenzoacrylonitrile as a core, and different substituents are taken as substituent groups; the deep red or near infrared flexible fluorescent organic crystal material is obtained by dissolving the powdery material with a proper solvent and slowly volatilizing and culturing, the fluorescent material has the advantages of cheap and easily obtained raw materials, simple preparation method, flexible crystal bending to a semicircle at any angle, good elastic mechanical property and the like, and can be applied to the aspects of flexible photoelectric devices, display materials, information storage materials or optical waveguide materials.

Inventors

  • ZHANG HONGYU
  • TANG BAOLEI
  • CHEN QUANLIANG

Assignees

  • 吉林大学

Dates

Publication Date
20260505
Application Date
20231222

Claims (6)

  1. 1. The flexible crystal material of the dibenzoyl acrylonitrile is characterized in that the flexible crystal material of the dibenzoyl acrylonitrile is prepared from a dibenzoyl acrylonitrile compound; The structural formula of the dibenzoacrylonitrile compound is shown as the formula (I): (I); dissolving the molecular powder of the dibenzonitrile into a good solvent, then adding a poor solvent, and slowly volatilizing the solvent at room temperature until needle-shaped elastic crystals are obtained to obtain the flexible dibenzonitrile crystal material; The good solvent is selected from dichloromethane, chloroform and acetone; the poor solvent is selected from petroleum ether, n-hexane, methanol and ethanol; The Ar structure is as follows: 、 、 、 、 、 、 、 、 、 ; The diphenylacrylonitrile molecules are flexible crystals, and the unit cell parameters are as follows: (1) The chemical formula is C 19 H 17 N 2 , the crystal material belongs to monoclinic system, the space group is P121/C1, a= 7.5710 (8) a, b= 17.6435 (18) a, c= 16.8668 (19) a, α=90°, β= 98.793 °, γ=90°, z=6, and the unit cell volume v= 2226.6 (4) a 3 ; (2) The chemical formula is C 20 H 19 N 2 , the crystal material belongs to an orthorhombic system, the space group is Pna21, a= 11.1327 (10) a, b= 36.568 (3) a, c= 7.7230 (5) a, α=90°, β=90°, γ=90°, z=8, and unit cell volume v= 3144.0 (4) a 3 ; (3) The chemical formula is C 25 H 22 N 2 , the crystal material belongs to monoclinic system, the space group is P121/n1, a= 12.3853 (10) a, b= 6.0975 (4) a, c= 23.2010 (18) a, α=90°, β= 101.919 °, γ=90°, z=4, and unit cell volume v= 1714.3 (2) a 3 ; (4) The chemical formula is C 19 H 17 FN 2 , the crystal material belongs to monoclinic system, the space group is C12/C1, a= 33.420 (2) a, b= 3.9340 (3) a, c= 22.9549 (16) a, α=90°, β= 104.405 °, γ=90°, z=8, and unit cell volume v= 2923.1 (4) a 3 ; (5) The chemical formula is C 19 H 16 F 2 N 2 , the crystal material belongs to monoclinic system, the space group is C12/C1, a= 34.992 (3) a, b= 3.9927 (2) a, c= 23.0491 (14) a, α=90°, β= 106.082 °, γ=90°, z=8, and unit cell volume v= 3094.2 (3) a 3 ; (6) The chemical formula is C 19 H 15 F 3 N 2 , the crystal material belongs to monoclinic system, the space group is C12/C1, a= 34.7691 (11) a, b= 4.00920 (10) a, c= 23.5274 (8) a, α=90°, β= 105.6190 °, γ=90°, z=8, and unit cell volume v= 3158.53 (17) a 3 ; (7) The chemical formula is C 20 H 16 F 3 N 2 , the crystal material belongs to monoclinic system, the space group is P121/C1, a= 12.6197 (8) a, b= 6.0908 (4) a, c= 23.2499 (16) a, α=90°, β= 102.252 °, γ=90°, z=4, and unit cell volume v= 1746.4 (2) a 3 ; (8) The chemical formula is C 20 H 16 F 3 N 2 , the crystal material belongs to an orthorhombic system, the space group of the crystal material is Pbca, a= 13.5622 (4) a, b= 10.0093 (3) a, c= 25.2061 (8) a, α=90°, β=90°, γ=90°, z=8, and unit cell volume v= 3421.68 (18) a 3 ; (9) The chemical formula is C 20 H 16 N 3 , the crystal material belongs to monoclinic system, the space group is P121/C1, a= 4.3143 (4) a, b= 10.9207 (10) a, c= 34.499 (3) a, α=90°, β= 92.132 °, γ=90°, z=4, and the unit cell volume v= 1624.3 (3) a 3 ; (10) The chemical formula is C 19 H 17 N 3 O 2 , the crystal material belongs to a triclinic system, the space group is P-1, a= 6.6635 (8) a, b= 7.2294 (9) a, c= 18.521 (3) a, α= 82.983 °, β= 89.166 °, γ= 64.384 °, z=2, and the unit cell volume v= 797.76 (18) a 3 .
  2. 2. The flexible crystal material of diphenylacrylonitrile according to claim 1, wherein the flexible crystal material of diphenylacrylonitrile molecules is bendable to a semicircular ring under the action of external force.
  3. 3. The flexible crystal material of dibenzoacrylonitrile according to claim 1, wherein said flexible crystal material of dibenzoacrylonitrile molecule can realize deep red or near infrared fluorescence emission under the irradiation of ultraviolet light.
  4. 4. Use of a flexible crystalline material of the dibenzoacrylonitrile type according to any one of claims 1-3 as a fluorescent material in a flexible active optical waveguide.
  5. 5. The use of the flexible crystalline material of the class of dibenzoacrylonitrile as a fluorescent material in flexible active optical waveguides as claimed in claim 4, wherein the flexible crystalline material of the class of dibenzoacrylonitrile molecules is placed on a silicon wafer and the waveguide emission of the crystalline material is observed at the other end of the crystal by irradiating one end of the flexible crystal with ultraviolet light.
  6. 6. The application of the flexible crystal material of the dibenzoacrylonitrile as a fluorescent material in a flexible active optical waveguide according to claim 5, wherein the intensity of ultraviolet light is not less than 80mW/cm 2 , and the wave band is 300-400 nm.

Description

Flexible crystal material of dibenzoacrylonitrile, preparation method and application thereof Technical Field The invention relates to the field of organic photoelectric functional materials, in particular to a flexible crystal material of dibenzoacrylonitrile and a preparation method and application thereof. Background In recent years, flexible electronic products have been rapidly developed and are gradually popularized in people's daily lives. The organic crystal material has the advantages of few defects, long-range order of structure, good light stability and heat stability, high carrier mobility and the like, and is an ideal material for preparing flexible organic electronic devices. However, the conventional organic crystal material is usually a brittle material, and is extremely easy to crack and unable to deform under the action of external force, which greatly limits the application of the material in the organic photoelectric field, especially in flexible electronic devices. Therefore, how to design and synthesize a flexible pure organic light emitting crystalline material becomes a key point of research in this field. Pure organic flexible crystal materials with elasticity or plasticity under the action of various external forces, but pure organic flexible crystal materials with deep red and near infrared fluorescence are extremely rare. However, the light emitting location of practical active optical waveguides is typically in the deep red to near infrared region. The light-emitting position of the existing flexible active optical waveguide material based on the organic crystal generally cannot reach the near infrared region, and is difficult to be compatible with the existing standard. The Chinese patent document with publication number of CN115286607A discloses a flexible crystal material of xanthone type, a preparation method and application thereof, wherein the phosphorescence emission peak position is in an obvious green light wavelength emission region, and cannot be well compatible with the existing optical waveguide application standard. Disclosure of Invention (One) solving the technical problems Aiming at the technical problems, the invention aims to develop a flexible deep red or near infrared fluorescent crystal material of the dibenzoacrylonitrile with simple preparation and good effect, and provides a preparation method based on a flexible crystal of a dibenzoacrylonitrile derivative and application of the flexible crystal material as a flexible fluorescent crystal material. The crystal prepared by the invention has good elasticity, can realize the function of an active optical waveguide, and provides a certain reference and reference for the application of the fluorescent crystal material in the fields of flexible devices, active optical waveguides and the like. (II) technical scheme A flexible crystal material of dibenzoacrylonitrile is prepared from dibenzoacrylonitrile compound; the structural formula of the dibenzoacrylonitrile compound is shown as the formula (I): Wherein Ar structure is benzene ring containing different substituent groups, and the substituent groups are one or more groups of halogen, cyano, nitro, methyl, trifluoromethyl or phenyl. Further, the Ar structure includes: The diphenylacrylonitrile molecules are flexible crystals, and the unit cell parameters include the following: (1) The chemical formula is C 19H17N2, the crystal material belongs to monoclinic system, the space group is P121/C1, Α=90°, β= 98.793 °, γ=90°, z=6, unit cell volume (2) The chemical formula is C 20H19N2, the crystal material belongs to an orthorhombic system, the space group is Pna21,Α=90°, β=90°, γ=90°, z=8, unit cell volume (3) The chemical formula is C 25H22N2, the crystal material belongs to monoclinic system, the space group is P121/n1,Α=90°, β= 101.919 °, γ=90°, z=4, unit cell volume (4) The chemical formula is C 19H17FN2, the crystal material belongs to monoclinic system, the space group is C12/C1,Α=90°, β= 104.405 °, γ=90°, z=8, unit cell volume (5) The chemical formula is C 19H16F2N2, the crystal material belongs to monoclinic system, the space group is C12/C1,Α=90°, β= 106.082 °, γ=90°, z=8, unit cell volume (6) The chemical formula is C 19H15F3N2, the crystal material belongs to monoclinic system, the space group is C12/C1,Α=90°, β= 105.6190 °, γ=90°, z=8, unit cell volume (7) The chemical formula is C 20H16F3N2, the crystal material belongs to monoclinic system, the space group is P121/C1,Α=90°, β= 102.252 °, γ=90°, z=4, unit cell volume (8) The chemical formula is C 20H16F3N2, the crystal material belongs to an orthorhombic system, the space group is Pbca,Α=90°, β=90°, γ=90°, z=8, unit cell volume (9) The chemical formula is C 20H16N3, the crystal material belongs to monoclinic system, the space group is P121/C1,Α=90°, β= 92.132 °, γ=90°, z=4, unit cell volume (10) The chemical formula is C 19H17N3O2, the crystal material belongs to a triclinic system, the space group is