CN105694860B - Luminescent material [Cd (tidc) 2] n and synthetic method - Google Patents

Luminescent material [Cd (tidc) 2] n and synthetic method Download PDF

Info

Publication number
CN105694860B
CN105694860B CN201610171128.3A CN201610171128A CN105694860B CN 105694860 B CN105694860 B CN 105694860B CN 201610171128 A CN201610171128 A CN 201610171128A CN 105694860 B CN105694860 B CN 105694860B
Authority
CN
China
Prior art keywords
tidc
htidc
pure
dissolved
dichloro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN201610171128.3A
Other languages
Chinese (zh)
Other versions
CN105694860A (en
Inventor
张淑华
张海洋
肖瑜
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Guangxi baolixing Lighting Technology Co., Ltd
Original Assignee
Guilin University of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Guilin University of Technology filed Critical Guilin University of Technology
Priority to CN201610171128.3A priority Critical patent/CN105694860B/en
Publication of CN105694860A publication Critical patent/CN105694860A/en
Application granted granted Critical
Publication of CN105694860B publication Critical patent/CN105694860B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008Supramolecular polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1007Non-condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14Macromolecular compounds
    • C09K2211/1408Carbocyclic compounds
    • C09K2211/1425Non-condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14Macromolecular compounds
    • C09K2211/1441Heterocyclic
    • C09K2211/1466Heterocyclic containing nitrogen as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • C09K2211/188Metal complexes of other metals not provided for in one of the previous groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

The invention discloses a kind of fluorescent material [Cd (tidc)2]nAnd synthetic method.Monomer molecule formula is:C18H10CdCl4N8O2, molecular weight is:624.55g/mol, Htidc are the 3,5 dichloro-salicylaldehydes contracting triazole schiff bases of 4 amino 1,2,4.It will analyze pure 3, and 5 dichloro-salicylaldehydes and analyze the pure triazole of 4 amino 1,2,4, and be dissolved in analysis straight alcohol, be heated to reflux and stir, filter, wash three times with analysis straight alcohol, it is dry, obtain part Htidc.Dried Htidc and the pure cadmium acetate of analysis are dissolved in and analyze pure N, in N ' dimethylformamides, distilled water is added, three days is stood in 80 DEG C of baking ovens.[Cd(tidc)2]nThe 512nm of 1316a.u. intensity fluorescence, under 800V photomultiplier, 3 times of amplification coefficient, generated in potassium persulfate solution 3262a.u. intensity and stable luminous are produced under 450nm incident light irradiation.Present invention process is simple, cost is cheap, chemical constituent is easily controllable, reproducible and yield is high.

Description

Luminescent material [Cd (tidc)2]nAnd synthetic method
Technical field
The present invention relates to a kind of luminescent material of stabilization [Cd (tidc)2]n, (Htidc is 3,5- dichloro-salicylaldehyde's contracting 4- ammonia The triazole of base -1,2,4 schiff bases) and synthetic method.
Background technology
Development of the modern luminescent material after many decades, oneself turns into the fields such as presentation of information, lighting source, photoelectric device Backing material, the effect to become more and more important is played for social development and technological progress.Particularly energy scarcity is present, and exploitation turns The luminescent material for changing efficiency high is that solve the problems, such as one of energy scarcity method.
The content of the invention
The purpose of the present invention is exactly to synthesize the excellent functional material of luminosity for design, utilizes micro- bottle of reaction method to synthesize [Cd(tidc)2]n
[Cd (tidc) of the present invention2]nMonomer molecule formula be:C18H10CdCl4N8O2, molecular weight is: 624.55, Htidc is 3,5- dichloro-salicylaldehyde's contracting 4- amino -1,2,4 triazole schiff bases, and crystal structural data is shown in Table one, bond distance's bond angle number According to being shown in Table two.
Table one:[Cd(tidc)2]nCrystallographic parameter
aR1=Σ | | Fo|–|Fc||/Σ|Fo|.b wR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table two:[Cd(tidc)2]nBond distanceWith bond angle °
Cd1—O1 2.190(7) C6—C5 1.293(18)
Cd1—O1i 2.190(7) C2—C3 1.403(15)
Cd1—N2ii 2.288(9) C7—N4 1.305(13)
Cd1—N2iii 2.288(9) N2—Cd1iv 2.288(9)
Cd1—N4 2.443(10) N2—N1 1.397(15)
Cd1—N4i 2.443(10) N2—C9 1.314(15)
Cl2—C5 1.747(12) N1—C8 1.323(18)
Cl1—C3 1.706(13) C5—C4 1.432(18)
O1—C2 1.261(12) C4—C3 1.386(16)
C1—C6 1.387(15) N4—N3 1.393(13)
C1—C2 1.462(16) C9—N3 1.354(15)
C1—C7 1.427(15) N3—C8 1.337(14)
Cd1—O1 2.190(7) C6—C5 1.293(18)
O1—Cd1—O1i 162.5(5) C3—C2—C1 114.9(10)
O1i—Cd1—N2iii 84.0(3) N4—C7—C1 127.3(11)
O1i—Cd1—N2ii 109.2(3) N1—N2—Cd1iv 124.6(7)
O1—Cd1—N2iii 109.2(3) C9—N2—Cd1iv 126.3(8)
O1—Cd1—N2ii 84.0(3) C9—N2—N1 107.8(10)
O1i—Cd1—N4i 76.0(3) C8—N1—N2 104.8(10)
O1i—Cd1—N4 93.0(3) C6—C5—Cl2 124.3(11)
O1—Cd1—N4 76.0(3) C6—C5—C4 121.1(12)
O1—Cd1—N4i 93.0(3) C4—C5—Cl2 114.5(10)
N2iii—Cd1—N2ii 84.1(5) C3—C4—C5 117.0(11)
N2iii—Cd1—N4i 156.3(3) C2—C3—Cl1 117.2(9)
N2ii—Cd1—N4 156.3(3) C4—C3—Cl1 118.7(10)
N2iii—Cd1—N4 90.4(4) C4—C3—C2 124.1(12)
N2ii—Cd1—N4i 90.4(4) C7—N4—Cd1 124.0(7)
N4i—Cd1—N4 103.2(5) C7—N4—N3 111.1(10)
C2—O1—Cd1 135.8(7) N3—N4—Cd1 123.8(7)
C6—C1—C2 119.3(10) N2—C9—N3 110.0(11)
C6—C1—C7 116.9(11) C9—N3—N4 129.7(10)
C7—C1—C2 123.8(10) C8—N3—N4 124.8(11)
C5—C6—C1 123.6(12) C8—N3—C9 105.3(11)
O1—C2—C1 122.7(10) N1—C8—N3 111.9(13)
O1—C2—C3 122.4(11)
Symmetry codes:(i)y,x,-z+1;(ii)x+1,y,z;(iii)y,x+1,-z+1;(iv)x-1,y,z.
[the Cd (tidc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure 3, the 5- dichloro-salicylaldehydes of 1.91g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles, It is dissolved in 30mL analysis straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, is analyzed with 10mL pure Ethanol washs three times, places and is dried at 50 DEG C, obtains part Htidc.By the dried Htidc of 0.056-0.112g and 0.054-0.108g, which analyzes pure cadmium acetate and is dissolved in 5mL, analyzes pure N, in N '-dimethyl formamide, is placed in micro- reaction bulb, then add Enter 5mL distilled water, three days are stood in 80 DEG C of baking ovens, there are yellow crystals to generate i.e. [Cd (tidc)2]n- cross single crystal diffractometer measure [Cd(tidc)2]nStructure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
(2) [Cd (tidc) obtained by step (1) is taken2]nThe pure N of analysis is dissolved in, concentration is made into N '-dimethyl formamide solvent For 5.0 × 10-6Mol/L solution, carry out fluorometric investigation, [Cd (tidc)2]nProduced under 450nm incident light irradiation The 512nm of 1316a.u. intensity fluorescence;Under 800V photomultiplier, 3 times of amplification coefficient, take 100 μ L are above-mentioned to prepare Solution be placed in 1mol/L potassium persulfate solutions (conducting medium), generate the luminous of 3262a.u. intensity, and in this condition Under, it can continue and stabilized illumination.
The present invention has the advantages that technique is simple, cost is cheap, chemical constituent is easily controllable, reproducible and yield is high.
Brief description of the drawings
Fig. 1 is the present invention [Cd (tidc)2]nStructure chart.
Fig. 2 is the present invention [Cd (tidc)2]n2 d plane picture.
Fig. 3 is the present invention [Cd (tidc)2]nTomograph.
Fig. 4 is the present invention [Cd (tidc)2]nFluorescence spectra.
Fig. 5 is the present invention [Cd (tidc)2]nElectrochemical luminescence spectrogram.
Embodiment
Embodiment 1:
[Cd (tidc) of the present invention2]nMolecular formula be:C18H10CdCl4N8O2, molecular weight is:624.55, Htidc is 3,5- dichloro-salicylaldehyde's contracting 4- amino -1,2,4 triazole schiff bases, and crystal structural data is shown in Table one, bond distance's bond angle number According to being shown in Table two.
[Cd(tidc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure 3, the 5- dichloro-salicylaldehydes of 1.91g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles, It is dissolved in 30mL analysis straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, is analyzed with 10mL pure Ethanol washs three times, places and is dried at 50 DEG C, obtains part Htidc.Yield:2.641g yield 96%.0.056g is dried The pure cadmium acetate of the analyses of rear Htidc and 0.054 is dissolved in 5mL and analyzes pure N, in N '-dimethyl formamide, is placed in micro- reaction bulb, 5mL distilled water is added, three days are stood in 80 DEG C of baking ovens, there are yellow crystals to generate i.e. [Cd (tidc)2]n.Yield:0.059g, Yield 63%.[Cd (tidc) is determined by single crystal diffractometer2]nStructure, crystal structural data is shown in Table one, bond distance's bond angle data It is shown in Table two.
(2) [Cd (tidc) obtained by step (1) is taken2]nThe pure N of analysis is dissolved in, concentration is made into N '-dimethyl formamide solvent For 5.0 × 10-5Mol/L solution, carry out fluorometric investigation, [Cd (tidc)2]nProduced under 450nm incident light irradiation The 512nm of 1316a.u. intensity fluorescence;Under 800V photomultiplier, 3 times of amplification coefficient, take 100 μ L are above-mentioned to prepare Solution be placed in 1mol/L potassium persulfate solutions (conducting medium), generate the luminous of 3262a.u. intensity, and in this condition Under, it can continue and stabilized illumination.
Embodiment 2:
[Cd (tidc) of the present invention2]nMolecular formula be:C18H10CdCl4N8O2, molecular weight is:624.55, Htidc is 3,5- dichloro-salicylaldehyde's contracting 4- amino -1,2,4 triazole schiff bases, and crystal structural data is shown in Table one, bond distance's bond angle number According to being shown in Table two.
[Cd(tidc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure 3, the 5- dichloro-salicylaldehydes of 1.91g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles, It is dissolved in 30mL analysis straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, is analyzed with 10mL pure Ethanol washs three times, places and is dried at 50 DEG C, obtains part Htidc.Yield:2.641g yield 96%.0.112g is dried Rear Htidc and 0.108g, which analyzes pure cadmium acetate and is dissolved in 5mL, analyzes pure N, in N '-dimethyl formamide, is placed in micro- reaction bulb In, 5mL distilled water is added, three days are stood in 80 DEG C of baking ovens, there are yellow crystals to generate i.e. [Cd (tidc)2]n.Yield: 0.118g, yield 63%.- [Cd (tidc) is determined by single crystal diffractometer2]n- structure, crystal structural data is shown in Table one, bond distance Bond angle data are shown in Table two.
(2) [Cd (tidc) obtained by step (1) is taken2]nThe pure N of analysis is dissolved in, concentration is made into N '-dimethyl formamide solvent For 5.0 × 10-5Mol/L solution, carry out fluorometric investigation, [Cd (tidc)2]nProduced under 450nm incident light irradiation The 512nm of 1316a.u. intensity fluorescence;Under 800V photomultiplier, 3 times of amplification coefficient, take 100 μ L are above-mentioned to prepare Solution be placed in 1mol/L potassium persulfate solutions (conducting medium), generate the luminous of 3262a.u. intensity, and in this condition Under, it can continue and stabilized illumination.

Claims (1)

  1. A kind of 1. luminescent material [Cd (tidc)2]n, it is characterised in that [Cd (tidc)2]nMolecular formula be:C18H10CdCl4N8O2, Molecular weight is:624.552, Htidc 3,5- dichloro-salicylaldehyde's contracting 4- amino -1,2,4 triazole schiff bases, crystal structural data One is shown in Table, bond distance's bond angle data are shown in Table two;[Cd(tidc)2]n1316a.u. intensity is produced under 450nm incident light irradiation 512nm fluorescence, under 800V photomultiplier, 3 times of amplification coefficient, in conducting medium potassium persulfate solution, produce 3262a.u. intensity and stable is luminous;
    Table one:[Cd(tidc)2]nCrystallographic parameter
    aR1=Σ | | Fo|–|Fc||/Σ|Fo|.bwR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
    Table two:[Cd(tidc)2]nBond distanceWith bond angle °
    Symmetry codes:(i)y,x,-z+1;(ii)x+1,y,z;(iii)y,x+1,-z+1;(iv)x-1,y,z;
    [the Cd (tidc)2]nSynthetic method concretely comprise the following steps:
    By analytically pure 3, the 5- dichloro-salicylaldehydes of 1.91g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles, 30mL is dissolved in Analyze in straight alcohol solution, be heated to reflux and have solid precipitation after stirring two hours, filter, washed with 10mL analysis straight alcohols Three times, place at 50 DEG C and dry, obtain part Htidc;0.056-0.112g dried Htidc and 0.054-0.108g are divided Analyse pure cadmium acetate and be dissolved in 5mL and analyze pure N, in N '-dimethyl formamide, be placed in micro- reaction bulb, add 5mL distilled water, Three days are stood in 80 DEG C of baking ovens, there are yellow crystals to generate i.e. [Cd (tidc)2]n
CN201610171128.3A 2016-03-23 2016-03-23 Luminescent material [Cd (tidc) 2] n and synthetic method Expired - Fee Related CN105694860B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610171128.3A CN105694860B (en) 2016-03-23 2016-03-23 Luminescent material [Cd (tidc) 2] n and synthetic method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610171128.3A CN105694860B (en) 2016-03-23 2016-03-23 Luminescent material [Cd (tidc) 2] n and synthetic method

Publications (2)

Publication Number Publication Date
CN105694860A CN105694860A (en) 2016-06-22
CN105694860B true CN105694860B (en) 2018-01-12

Family

ID=56231413

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610171128.3A Expired - Fee Related CN105694860B (en) 2016-03-23 2016-03-23 Luminescent material [Cd (tidc) 2] n and synthetic method

Country Status (1)

Country Link
CN (1) CN105694860B (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102503963B (en) * 2011-09-13 2014-04-23 江西师范大学 Zinc metal-organic coordination polymer and preparation method thereof
JP6009957B2 (en) * 2013-02-05 2016-10-19 株式会社日本触媒 Organometallic complex

Also Published As

Publication number Publication date
CN105694860A (en) 2016-06-22

Similar Documents

Publication Publication Date Title
CN105693637B (en) Luminescent material [Cu (tibc)2]nAnd synthetic method
CN105859778A (en) Pure organic phosphorescent material with afterglow luminescence performance and ultra-long service life, method for preparing pure organic phosphorescent material and application thereof
CN103570761A (en) Copper complex/composite luminescent material sensitive to oxygen gas as well as preparation method thereof and application thereof on oxygen sensing device
CN107286186A (en) Hydrogen sulfide fluorescence probe and its preparation method and application
CN113831756A (en) Red fluorescent protein two-photon photosensitive dye and preparation method and application thereof
CN105694860B (en) Luminescent material [Cd (tidc) 2] n and synthetic method
CN104927841B (en) A kind of near-infrared organic fluorescent dye with mechanical response
CN109438721A (en) A kind of cadmium base luminescent metal organic framework material and its preparation method and application with high-fluorescence quantum yield
CN105694861B (en) Luminescent material [Mn (tibc)2]nAnd synthetic method
CN105801504B (en) Luminescent material [Cd (tibc)2]nAnd synthetic method
CN108997439B (en) Metal iridium complex prepared based on 5-aldehyde-1, 10-phenanthroline and application thereof
CN105801503B (en) Luminescent material [Zn (tidc)2]nAnd synthetic method
CN105837568B (en) A kind of fluorenyl β carbolines class compound, its application and preparation method as luminous organic material and aggregation inducing Fluorescence Increasing material
CN108314636A (en) A kind of polyaryl sulphur oscillation luminescent material and its preparation method and application
CN105694867B (en) Fluorescent material [Cu2Na2(mtyp)2(CH3COO)2(H2O)3]nAnd synthetic method
CN104230967B (en) Fluorescent material Zn2(hfoac)4(phen)2and synthetic method
CN1811430A (en) Singlet oxygen europium coordination compound fluorescent probe and application thereof
CN105694862B (en) Luminescent material [Zn (tibc)2]nAnd synthetic method
CN105647521B (en) Luminescent material [Mn (tidc)2]nAnd synthetic method
CN104263352B (en) Fluorescent material Zn (hfoac)2(phen) H2o and synthetic method
CN102731479A (en) Organic ligand, rare earth organic fluorescent probe material thereof and preparation method thereof
CN105801502B (en) Luminescent material Cu2(etmp)4And synthetic method
CN110759834B (en) Fluorescent probe for identifying aluminum ions and preparation method and application thereof
CN104130773B (en) Fluorescent material Zn2(hfoac)4(4,4-pybi)2And synthetic method
CN105713020A (en) Fluorescent material [Cu(tidc)2]n and synthesis method

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20191107

Address after: 531105 floor 1-2, building 1, No.146, Wuhua Avenue, Guangxi ASEAN Economic and Technological Development Zone, Nanning City, Guangxi Zhuang Autonomous Region (excluding the top floor)

Patentee after: Guangxi baolixing Lighting Technology Co., Ltd

Address before: 541004 the Guangxi Zhuang Autonomous Region Guilin Construction Road No. 12

Patentee before: Guilin University of Technology

CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20180112

Termination date: 20210323