CN113136200A - Circular polarization luminous liquid crystal physical gel material and preparation method thereof - Google Patents
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 77
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
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- 238000010438 heat treatment Methods 0.000 claims abstract description 24
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 238000004020 luminiscence type Methods 0.000 claims description 14
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- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 claims description 9
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 claims description 4
- RDISTOCQRJJICR-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCC)=CC=C1C1=CC=C(C#N)C=C1 RDISTOCQRJJICR-UHFFFAOYSA-N 0.000 claims description 3
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 238000001338 self-assembly Methods 0.000 abstract description 4
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Abstract
The invention belongs to the technical field of luminescent materials, and particularly relates to a circular polarization luminescent liquid crystal physical gel material and a preparation method thereof. The circular polarization luminous liquid crystal physical gel material comprises a chiral luminous material, an organogelator and a room temperature nematic liquid crystal, and is prepared by the following method: (1) weighing a chiral luminescent material, an organogel factor and a room-temperature nematic liquid crystal according to a certain mass ratio, and adding the chiral luminescent material, the organogel factor and the room-temperature nematic liquid crystal into a sample bottle with a plug; (2) heating to completely dissolve all the components to form a uniform and transparent solution; (3) stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminous liquid crystal physical gel material. According to the invention, the chiral luminescent material is introduced into the room-temperature nematic liquid crystal, and the three-dimensional network structure formed by self-assembly of the gel factors is adopted as the supporting material, so that the circular polarization luminescent liquid crystal material with the self-supporting performance, which is simple in preparation process, good in application performance and excellent in circular polarization luminescent performance, can be obtained.
Description
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to a circular polarization luminescent liquid crystal physical gel material and a preparation method thereof.
Background
Circular Polarized Luminescence (CPL) refers to a phenomenon in which a chiral luminescent system emits left-handed and right-handed Circularly Polarized light with differences after being excited. Due to the unique structure and properties of the circularly polarized light material, the circularly polarized light material has wide application prospects in the fields of asymmetric synthesis, chemical sensors, 3D display and the like. The research on the circular polarization luminescent material not only can well reveal the structural information of the chiral molecules in an excited state, but also is helpful for deeply understanding the generation, transmission and amplification mechanisms of chirality.
Circularly polarized luminescence asymmetry factor glumIs one of the important parameters for characterizing the circular polarized luminescence property, glum=2(IL-IR)/(IL+IR) In which ILAnd IRThe luminous intensity of the left-handed circularly polarized light and the luminous intensity of the right-handed circularly polarized light are respectively when g islumWhen it is 0, it means that the system emits light having no polarization, and when g islumWhen the value is +/-2, the system emits complete left-handed or right-handed circularly polarized light (positive values are left-handed circularly polarized light, and negative values are right-handed circularly polarized light). glumThe value directly determines the practical application prospect of the circular polarization luminescent material, so that how to improve the luminescent asymmetry factor value is one of the key problems in the field of the circular polarization luminescent material.
The chiral liquid crystal has a spiral stacked assembly structure, and researches show that the construction of the luminous chiral liquid crystal is used for preparing the chiral liquid crystal with high glumAn efficient method for the CPL material. Such a high glumThe CPL emission of the value is mainly attributed to the chiral liquid crystal specific helical assembly process which can realize the amplification of chirality, and in addition, when the helical pitch of the chiral liquid crystal is matched with the luminescence wavelength of the luminescent group, the selective reflection of the chiral liquid crystal can further improve the g of the circular polarization luminescence liquid crystal materiallumValue, g producedlumValues of typically up to 10-1Magnitude. The chiral circular polarization luminescent liquid crystal material reported at present mainly comprises two main classes of host-guest doped circular polarization luminescent liquid crystal materials and non-doped circular polarization luminescent liquid crystal materials, wherein the host-guest doped circular polarization luminescent liquid crystal materials attract the attention of scientific researchers due to the advantages of multiple classes, simple preparation, easy performance regulation and the like. The host-guest doped circular polarization luminescent liquid crystal material is mainly prepared by doping a chiral agent into luminescent nematic liquid crystal or byPrepared by doping a chiral luminescent dye into a nematic liquid crystal. The subject group of professor is doped with chiral fluorescent dye micromolecule R/S-BINOL-CN into nematic liquid crystal E7, the influence of the doping amount on the circular polarization luminous intensity is researched, the research finds that the pitch of cholesteric liquid crystal is gradually reduced along with the increase of the doping amount of the R/S-BINOL-CN, the circular polarization luminous intensity is in an increasing trend, and when the doping amount is 2 wt%, g islumValues of. + -. 0.4 can be achieved (Chemistry-A European Journal,2018,24(48): 12607-12612). Further, g is prepared by doping a nematic liquid crystal E7 with a small molecule chiral agent and a small molecule luminescent compoundlumThree-component host-guest doping type circular polarization luminescent liquid crystal materials with the value of 1.42 (Chemical Communications,2019,55(35): 5179-.
At present, great research progress is reported on the aspects of preparation methods, performance regulation and control and the like of the host-guest doping type circular polarization luminescent liquid crystal material, but some defects also exist, most of the reported liquid crystal materials used by the host-guest doping type circular polarization luminescent liquid crystal are small-molecule room-temperature nematic liquid crystal, and have good fluidity at room temperature, so the prepared circular polarization luminescent liquid crystal material needs an additional container such as a liquid crystal box for containing, the device packaging is complex, and meanwhile, the fluidity of the liquid crystal also enables the spiral structure of the chiral luminescent liquid crystal to be in dynamic change, the circular polarization luminescent performance is unstable, and the practical application of the circular polarization luminescent liquid crystal material is not facilitated.
Disclosure of Invention
The invention aims to provide a circular polarization luminous liquid crystal physical gel material and a preparation method thereof aiming at the defects in the prior art, and a series of novel circular polarization luminous liquid crystal physical gel materials are prepared by introducing a physical cross-linking network into a host-guest doped circular polarization luminous liquid crystal material. The physical gel network formed by self-assembly of the organogel factors is utilized to anchor the liquid crystal, limit the movement of the liquid crystal, improve the stability of the circular polarization luminescence performance of the host-guest doped circular polarization luminescence liquid crystal material, realize the amplification of the circular polarization luminescence signal by utilizing the self-assembly process of the chiral liquid crystal, and improve the physical gel material of the circular polarization luminescence liquid crystalMaterial circular polarization luminescence asymmetry factor glumThe novel circular polarization luminescent liquid crystal material with the self-supporting performance, which has the advantages of simple preparation process, good application performance and excellent circular polarization luminescent performance, is obtained.
The invention is realized by the following modes:
a circular polarization luminous liquid crystal physical gel material comprises a chiral luminous material, an organogelator and a room-temperature nematic liquid crystal.
Further, the chemical structure of the chiral luminescent material is shown as formula (I):
wherein m1 and m2 are the number of methylene groups, 2 is more than or equal to m1 is less than or equal to 12, and 2 is more than or equal to m1 is less than or equal to 12.
Further, the chemical structure of the organogelator is shown as formula (II):
wherein m is the number of carbon atoms in the alkyl chain, and m is more than or equal to 12 and less than or equal to 18.
Further, the room-temperature nematic liquid crystal is one or more selected from 4' -n-pentyl-4-cyanobiphenyl (5CB), 4' -n-pentyloxy-4-cyanobiphenyl (5OCB), 4' -n-heptyl-4-cyanobiphenyl (7CB), 4' -n-octyloxy-4-cyanobiphenyl (8OCB), and 4' -n-pentyl-4-cyanobiphenyl (5 CT).
Further, the circular polarization luminescence liquid crystal physical gel material comprises the following components in percentage by mass: 80-97% of room-temperature nematic liquid crystal, 2-10% of organogelator and 1-10% of chiral luminescent material.
The preparation method of the circular polarization luminous liquid crystal physical gel material comprises the following steps: adding the chiral luminescent material, the organogelator and the room-temperature nematic liquid crystal into a sample bottle with a plug according to the mass percentage, heating to completely dissolve all the components to form a uniform and transparent solution, and stopping heating the sample and cooling to the room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The invention has the beneficial effects that:
compared with the prior art, the invention has the beneficial effects that: according to the invention, the chiral luminescent material is introduced into the room-temperature nematic liquid crystal, and the three-dimensional network structure formed by self-assembly of the gel factors is used as a supporting material, and the three-dimensional network structure formed by the gel factors has an anchoring effect on the liquid crystal and can limit the fluidity of the room-temperature nematic liquid crystal, so that the circular polarization luminescent liquid crystal physical gel material prepared by the invention has stable luminescent performance, has self-supporting property, does not need other containers for containing, and is simple in device packaging, so that the circular polarization luminescent liquid crystal material has good application performance and wide application prospect.
Drawings
FIG. 1 is a fluorescence emission diagram of a physical gel of a circularly polarized light-emitting liquid crystal in example 1 of the present invention.
Fig. 2 is a CPL spectrum of the physical gel of the circularly polarized light-emitting liquid crystal in embodiment 1 of the present invention.
FIG. 3 is a CD spectrum of a physical gel of a circularly polarized light-emitting liquid crystal in example 1 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the present invention is not limited thereto.
Table 1 shows the chemical structures of the gelators referred to in the specific examples; table 2 shows the chemical structures of the chiral luminescent molecules involved in the specific examples:
TABLE 1 chemical Structure of part of gelators
TABLE 2 chemical Structure of chiral luminescent molecules
Gel-sol transition temperature (T) of circular polarization luminous liquid crystal physical gel materialGS) The test is carried out by adopting an inclined test tube method: inserting a test tube with a plug containing 1g of circular polarization luminous liquid crystal physical gel material into an oil bath pot, heating at a speed of 2 ℃/min, inclining the test tube when the temperature is raised to a set temperature, if the material can flow right, defining the temperature as gel dissociation temperature, continuing heating, and defining the temperature as gel-sol transition temperature (T) when the material is completely dissolved into liquidGS)。
Example 1
Adding 10.06g of chiral luminescent material C10.06g, 10.02g of organogel factor G10.02g and 0.92g of room-temperature nematic liquid crystal 4' -n-pentyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 120 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.31.
Example 2
Adding 10.06g of chiral luminescent material C10.06g, 10.04g of organogel factor G10 and 0.90g of room-temperature nematic liquid crystal 4' -n-pentyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 130 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.30.
Example 3
Adding 10.06g of chiral luminescent material C10.06g, 10.06g of organogel factor G10 g and 0.88g of nematic liquid crystal 4' -n-amyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 132 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.26.
Example 4
Adding 10.06g of chiral luminescent material C10.06g, 10.08g of organogel factor G10 and 0.86g of room-temperature nematic liquid crystal 4' -n-amyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 136 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.19.
Example 5
Adding 10.06g of chiral luminescent material C10.06g, 10.04g of organogel factor G10 and 0.90g of room-temperature nematic liquid crystal 4' -n-pentyloxy-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 128 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.28.
Example 6
Adding 20.06g of chiral luminescent material C20, 10.04g of organogel factor G10 and 0.90g of room-temperature nematic liquid crystal 4' -n-pentyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 129 ℃,circularly polarized luminescence asymmetry factor glumThe value was-0.29.
Example 7
Adding 30.06g of chiral luminescent material C30, 10.02g of organogel factor G10 and 0.92g of room-temperature nematic liquid crystal 4' -n-amyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 110 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.31.
Example 8
Adding 10.06g of chiral luminescent material C10, 20.02g of organogel factor G20 and 0.92g of room-temperature nematic liquid crystal 4' -n-amyl-4-cyanobiphenyl into a sample bottle with a plug in sequence, heating to completely dissolve all the components to obtain a uniform and transparent solution, stopping heating, and naturally cooling to room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
The gel-sol transition temperature of the physical gel material of the circularly polarized luminous liquid crystal obtained in the embodiment is 128 ℃, and the asymmetric factor g of the circularly polarized luminous liquid crystal islumThe value was-0.30.
The figure presents the characterization results by taking the product obtained in the example 1 as a representative, and the products obtained in other examples can obtain basically consistent characterization results.
Claims (6)
1. The physical gel material of the circular polarization luminous liquid crystal is characterized by comprising a chiral luminous material, an organogelator and a room-temperature nematic liquid crystal.
2. The physically gelled material of a circularly polarized light-emitting liquid crystal according to claim 1, wherein the chemical structure of the chiral light-emitting material is as shown in formula (I):
wherein m1 and m2 are the number of methylene groups, 2 is more than or equal to m1 is less than or equal to 12, and 2 is more than or equal to m1 is less than or equal to 12.
4. The physical gel material of claim 1, wherein the room temperature nematic liquid crystal is selected from one or more of 5CB (4 ' -n-pentyl-4-cyanobiphenyl), 5OCB (4 ' -n-pentyloxy-4-cyanobiphenyl), 7CB (4 ' -n-heptyl-4-cyanobiphenyl), 8OCB (4 ' -n-octyloxy-4-cyanobiphenyl) and 5CT (4 ' -n-pentyl-4-cyanobiphenyl).
5. The circular polarization luminescence liquid crystal physical gel material according to any one of claims 1 to 4, characterized by comprising the following components in percentage by mass: 80-97% of room-temperature nematic liquid crystal, 2-10% of organogelator and 1-10% of chiral luminescent material.
6. The preparation method of the circular polarization luminescence liquid crystal physical gel material of any one of claims 1 to 5, comprising the following steps: adding the chiral luminescent material, the organogelator and the room temperature nematic liquid crystal into a sample bottle with a plug according to the mass percent in claim 5, heating to completely dissolve all the components to form a uniform and transparent solution, and stopping heating the sample and cooling to the room temperature to obtain the circular polarization luminescent liquid crystal physical gel material.
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CN113698943A (en) * | 2021-08-20 | 2021-11-26 | 华中科技大学 | Liquid crystal gel with light-emitting and light-responding characteristics, preparation method and application |
CN115305098A (en) * | 2022-08-23 | 2022-11-08 | 华中科技大学 | Luminous cholesteric liquid crystal gel, preparation method and application |
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