CN101544650A - Iodo-copper phthalocyanine nano-bar material and synthesizing method thereof - Google Patents
Iodo-copper phthalocyanine nano-bar material and synthesizing method thereof Download PDFInfo
- Publication number
- CN101544650A CN101544650A CN200810102696A CN200810102696A CN101544650A CN 101544650 A CN101544650 A CN 101544650A CN 200810102696 A CN200810102696 A CN 200810102696A CN 200810102696 A CN200810102696 A CN 200810102696A CN 101544650 A CN101544650 A CN 101544650A
- Authority
- CN
- China
- Prior art keywords
- iodo
- copper phthalocyanine
- synthetic method
- bar material
- deionized water
- 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.)
- Granted
Links
Images
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention provides an iodo-copper phthalocyanine nano-bar material. An iodo-copper phthalocyanine nano-bar is 50-200 nm in diameter and 1-15 microns in length, and the molecular structural formula of iodo-copper phthalocyanine is showed as (I). The invention also discloses a synthesizing method of the iodo-copper phthalocyanine nano-bar material, comprising the steps of mixing and placing 4-iodo-phthalic nitrile, copper powder or cupric salt, surface active agent and deionized water in a reaction kettle, sealing and heating the mixture for more than 10 h under a reaction temperature of 150-180 DEG C, cooling, collecting deposition, washing till the pH value is 6-7, and drying the deposition. The invention adopts water with wide source and low price as reaction medium, thereby greatly avoiding pollution of organic solvent to the environment and being environment-friendly. Meanwhile, synthesis and structure preparation are integrated so as to save working procedures.
Description
Technical field
The invention belongs to the technical field of organic nano material, be specifically related to iodo-copper phthalocyanine nano-bar material and synthetic method thereof.
Background technology
Iodo-copper phthalocyanine belongs to phthalocyanine derivates, phthalocyanine derivates has unusual light, electricity, heat, magnetic property and as the huge application potential of functional materialss such as novel molecular conductor, molecular magnet, molecular electronic components and parts, is attracting the more and more denseer research interest of people.But the synthetic organic solvent (as: chlorobenzene that mainly is based on that the iodo-copper phthalocyanine of bibliographical information is arranged at present, oil of mirbane) as the synthetic (B.N.Achar of reaction medium, Synth.React.Inorg.Met.Org.Chem., 2000,30,719-734), and this type of organic solvent belongs to high poison, not only there is potential safety hazard in high boiling solvent in experimentation, and also can cause suitable harm to our living environment.
The iodo-copper phthalocyanine nano material belongs to the organic nano material category, very tempting application prospect is arranged, in recent years along with the development of organic nano material, phthalocyanines organic materials nanometer technology of preparing also there is corresponding exploration, generally be redeposition or physical vaporous deposition (PVD) (Q.X.Tang by raw material, Adv.Mater.2006,18,65～68.).These methods not only can repeat the shape difference but also need hot conditions and be not suitable for preparing on a large scale nano material.This just presses for us and seeks a kind of preparation method who makes things convenient for cheapness to have commercial value.
Summary of the invention
The object of the present invention is to provide a kind of iodo-copper phthalocyanine nano-bar material.
Another object of the present invention is to provide the synthetic method of iodo-copper phthalocyanine nano-bar material.
The diameter of iodo-copper phthalocyanine nano-bar material of the present invention is 50～200 nanometers, and length is 1～15 micron, and the molecular structural formula of described iodo-copper phthalocyanine is as follows:
The synthetic method of iodo-copper phthalocyanine nano-bar material of the present invention: 4-iodo phthalic nitrile, copper powder or mantoquita, tensio-active agent, deionized water mixing are placed reactor, the sealing back is heated more than 10 hours under 150～180 ℃ of temperature of reaction, cooling back collecting precipitation, wash to pH be 6～7, be preferably 7, to precipitate drying, promptly obtain the iodo-copper phthalocyanine nano-bar material of purifying.
The consumption mol ratio of described iodo phthalic nitrile and copper powder or mantoquita is 2～4:1, is preferably 4:1
Described tensio-active agent is 0～3mg:1ml with going dried up usage ratio, is preferably 2～3mg:1ml; When not adding tensio-active agent, productive rate can reduce.
The usage ratio of described iodo phthalic nitrile and deionized water is 7mmol:100～150mg, is preferably 7mmol:100mg.
Described washing is water successively preferably, hydrochloric acid soln, FeCl
3The solution soaking washing; FeCl
3Solution and hydrochloric acid soln replace more than the washed twice, use deionized water wash again.
Described mantoquita is preferably venus crystals.
Described tensio-active agent is preferably sodium laurylsulfonate (SDS).
The concentration of described hydrochloric acid soln is preferably 1～2N.
Described FeCl
3Solution is preferably saturated solution.
The synthetic method of iodo-copper phthalocyanine nano-bar material of the present invention, its advantage are to adopt wide, the low-cost water in source as reaction medium, have avoided the pollution of organic solvent to environment greatly, and be environmentally friendly; Synthetic simultaneously and structure prepares the integrated operation of more saving, and the product nanorod structure that obtains can further be expanded the application prospect of material.
Description of drawings
Fig. 1. the uv absorption spectra of the iodo-copper phthalocyanine nano-bar material of the embodiment of the invention 1 preparation.
Fig. 2. the stereoscan photograph of the iodo-copper phthalocyanine nano-bar material of the embodiment of the invention 1 preparation.
Embodiment
The present embodiment agents useful for same is analytical pure, is obtained by commerce, does not need to be further purified.
Reacting precursor 4-iodo phthalic nitrile of the present invention adopts the method for document to make (as C.C.Leznoff, Can.J.Chem., 1995,73,435～443), also can use the commercial goods.
2.5M sulphuric acid soln 20ml is chilled to-10 ℃ in advance, (1.5g 0.0105mol) slowly adds in this sulphuric acid soln with the amino phthalic nitrile of 4-.Be mixed with solution 0.82g Sodium Nitrite adds in 2～3ml water, under the situation that the existence of stirring is arranged, controlled temperature slowly is added dropwise to reaction solution at-10～0 ℃ with this sodium nitrite solution, and this process need is more than lasting half an hour.Reaction mixture is by quick suction filtration then, cold filtrate is added into the cold KI (1.893g of 10.5ml, 11.2mmol) in the solution, mixture is raised to room temperature under the situation that the existence of stirring is arranged, reaction solution is introduced in the 500ml cold water, is collected by quick suction filtration black solid, then filter cake is dissolved in ethyl acetate, and to use cold water, mass concentration successively be 5%NaHCO
3Solution, cold water, saturated Na
2S
2O
3Solution, water, ethyl acetate layer is emitted in extraction, adds excessive MgSO
4Drying was used post to separate petrol ether/ethyl acetate (v/v=1:1) at last and was crossed the post separation.Productive rate 50%.
The synthetic route of iodo-copper phthalocyanine nano-bar material of the present invention is as follows:
Embodiment 1
With 4-iodo phthalic nitrile (1.4mmol), copper powder (0.35mmol), tensio-active agent (SDS, 20mg) placing volume in the lump is the reactor of 12ml, adds deionized water to still volumetrical 80%, and mixture stirs into white emulsion earlier, sealing is put into baking oven after reacting 3 days under 180 ℃ of conditions then, allow its naturally cooling, take out reactor, collect dark blue precipitate.Water successively, 1.0N hydrochloric acid soln, saturated FeCl
3The solution soaking washing.In order to remove unreacted copper powder, saturated FeCl
3Solution and 1.0N hydrochloric acid soln replace washed twice, again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 26%.
Gained iodo-copper phthalocyanine molecular structure is analyzed (UV-vis): Q band 690nm by ultra-violet absorption spectrum such as accompanying drawing 1, and B is with 350nm.Mass spectroscopy (Tof-MS): 1079.4.Ultimate analysis (Anal.Calcd.): CuPTI measured value (calculated value): C36.02 (35.59), N10.17 (10.38), H1.64 (1.12).2 as can be known with reference to the accompanying drawings, and gained iodo-copper phthalocyanine nano material is a large amount of nanometer rod, and its diameter is 100～200 nanometers, and length is 5～10 microns.
Sign for molecular structure has been passed through uv-absorbing, mass spectrum, and ultimate analysis, pattern is given and sign by scanning electron microscope, shows according to the inventive method, has finally synthesized the iodo-copper phthalocyanine nano rod of pattern homogeneous on a large scale.
Embodiment 2
With 4-iodo phthalic nitrile (1.4mmol), copper powder (0.35mmol), tensio-active agent (SDS, 20mg) placing volume in the lump is the reactor of 12ml, adds deionized water to still volumetrical 80%, and mixture stirs into white emulsion earlier, sealing is put into baking oven after reacting 3 days under 150 ℃ of conditions then, allow its naturally cooling, take out reactor, collect dark blue precipitate.Water successively, 1.0N hydrochloric acid soln, saturated FeCl
3The solution soaking washing.In order to remove unreacted copper powder, saturated FeCl
3Solution and 1.0N hydrochloric acid soln replace washed twice, again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 24%.Gained iodo-copper phthalocyanine nano rod, its diameter are 100～200 nanometers, and length is 5～15 microns.
Embodiment 3
With 4-iodo phthalic nitrile (1.4mmol), copper powder (0.35mmol), tensio-active agent (SDS, 20mg) placing volume in the lump is the reactor of 12ml, adds deionized water to still volumetrical 80%, and mixture stirs into white emulsion earlier, sealing is put into baking oven after reacting 10 hours under 180 ℃ of conditions then, allow its naturally cooling, take out reactor, collect dark blue precipitate.Use hot water successively, 1.0N hydrochloric acid soln, saturated FeCl
3The solution soaking washing.In order to remove unreacted copper powder, saturated FeCl
3Solution and 1.0N hydrochloric acid soln replace washed twice, again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 18%.Gained iodo-copper phthalocyanine nano rod, its diameter are 50～100 nanometers, and length is 1～10 micron.
Embodiment 4
With 4-iodo phthalic nitrile (1.4mmol), copper powder (0.7mmol), tensio-active agent (SDS, 30mg) placing volume in the lump is the reactor of 12ml, adds deionized water to still volumetrical 80%, and mixture stirs into white emulsion earlier, sealing is put into baking oven after reacting 3 days under 180 ℃ of conditions then, allow its naturally cooling, take out reactor, collect dark blue precipitate.Water successively, 1.0N hydrochloric acid soln, saturated FeCl3 solution soaking washing.In order to remove unreacted copper powder, saturated FeCl3 solution and 1.0N hydrochloric acid soln replace washed twice, again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 28%.Gained iodo-copper phthalocyanine nano rod, its diameter are 100～200 nanometers, and length is 5～10 microns.
Embodiment 5
With 4-iodo phthalic nitrile (1.4mmol), venus crystals (0.35mmol), tensio-active agent (SDS, 20mg) placing volume in the lump is the reactor of 12ml, adds deionized water to still volumetrical 80%, and mixture stirs into white emulsion earlier, sealing is put into baking oven after reacting 3 days under 180 ℃ of conditions then, allow its naturally cooling, take out reactor, collect dark blue precipitate.Use hot water successively, saturated salt acid solution, washing by soaking.Again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 12%.Gained iodo-copper phthalocyanine nano rod, its diameter are 50～100 nanometers, and length is 1～15 micron.
Embodiment 6
With 4-iodo phthalic nitrile (1.4mmol), copper powder (0.35mmol), tensio-active agent (SDS, 20mg) placing volume in the lump is the reactor of 12ml, adds deionized water to still volumetrical 80%, and mixture stirs into white emulsion earlier, sealing is put into baking oven after reacting 5 days under 180 ℃ of conditions then, allow its naturally cooling, take out reactor, collect dark blue precipitate.Use hot water successively, 1.0N hydrochloric acid soln, saturated FeCl
3The solution soaking washing.In order to remove unreacted copper powder, saturated FeCl
3Solution and 2.0N hydrochloric acid soln replace washed twice, again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 27%.Gained iodo-copper phthalocyanine nano rod, its diameter are 50～200 nanometers, and length is 1～15 micron.
Embodiment 7
With 4-iodo phthalic nitrile (1.4mmol), copper powder (0.35mmol), placing volume in the lump is the reactor of 12ml, add deionized water to still volumetrical 80%, mixture stirs into white emulsion earlier, and sealing is put into baking oven and allowed its naturally cooling in reaction under 180 ℃ of conditions after 3 days then, take out reactor, collect dark blue precipitate.Use hot water successively, 1.0N hydrochloric acid soln, saturated FeCl
3The solution soaking washing.In order to remove unreacted copper powder, saturated FeCl
3Solution and 1.0N hydrochloric acid soln replace washed twice, again with deionized water wash to pH=7, precipitation was placed 50 ℃ of baking oven inner dryings 24 hours, productive rate is 6%.Gained iodo-copper phthalocyanine nano rod, its diameter are 50～100 nanometers, and length is 5～15 microns.
Claims (10)
1. iodo-copper phthalocyanine nano-bar material is characterized in that: described iodo-copper phthalocyanine nano rod diameter is 50～200 nanometers, and length is 1～15 micron, and described iodo-copper phthalocyanine has following molecular structure:
2. the synthetic method of iodo-copper phthalocyanine nano-bar material according to claim 1, it is characterized in that: 4-iodo phthalic nitrile, copper powder or mantoquita, tensio-active agent, deionized water are mixed placing reactor, the sealing back is heated more than 10 hours under 150～180 ℃ of temperature of reaction, cooling back collecting precipitation, washing is 6～7 until pH, to precipitate drying, promptly obtain the iodo-copper phthalocyanine nano-bar material of purifying.
3. synthetic method according to claim 2 is characterized in that: the consumption mol ratio of described iodo phthalic nitrile and copper powder or mantoquita is 2～4:1; Described tensio-active agent is 0～3mg:1ml with going dried up usage ratio; The usage ratio of described iodo phthalic nitrile and deionized water is 7mmol:100～150mg.
4. synthetic method according to claim 3 is characterized in that: the consumption mol ratio of described iodo phthalic nitrile and copper powder or mantoquita is 4:1; Described tensio-active agent is 2～3mg:1ml with going dried up usage ratio; The usage ratio of described iodo phthalic nitrile and deionized water is 7mmol:100mg.
5. according to claim 2,3 or 4 described synthetic methods, it is characterized in that: described mantoquita is a venus crystals.
6. according to claim 2,3 or 4 described synthetic methods, it is characterized in that: described tensio-active agent is a sodium laurylsulfonate.
7. synthetic method according to claim 2 is characterized in that: described pH is 7.
8. synthetic method according to claim 2 is characterized in that: described washing is water successively, hydrochloric acid soln, FeCl
3The solution soaking washing; FeCl
3Solution and hydrochloric acid soln replace more than the washed twice, use deionized water wash again.
9. synthetic method according to claim 8 is characterized in that: the concentration of described hydrochloric acid soln is 1～2N.
10. synthetic method according to claim 8 is characterized in that: described FeCl
3Solution is saturated solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101026963A CN101544650B (en) | 2008-03-25 | 2008-03-25 | Iodo-copper phthalocyanine nano-bar material and synthesizing method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101026963A CN101544650B (en) | 2008-03-25 | 2008-03-25 | Iodo-copper phthalocyanine nano-bar material and synthesizing method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101544650A true CN101544650A (en) | 2009-09-30 |
| CN101544650B CN101544650B (en) | 2011-02-02 |
Family
ID=41192044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008101026963A Active CN101544650B (en) | 2008-03-25 | 2008-03-25 | Iodo-copper phthalocyanine nano-bar material and synthesizing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101544650B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103087082A (en) * | 2011-10-28 | 2013-05-08 | 国家纳米科学中心 | Porphyrin-phthalocyanine pentaplet, preparation method and applications thereof |
| CN113912613A (en) * | 2021-09-23 | 2022-01-11 | 鞍山七彩化学股份有限公司 | Method for preparing halogen substituent phthalocyanine blue and halogen substituent phthalocyanine blue |
-
2008
- 2008-03-25 CN CN2008101026963A patent/CN101544650B/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103087082A (en) * | 2011-10-28 | 2013-05-08 | 国家纳米科学中心 | Porphyrin-phthalocyanine pentaplet, preparation method and applications thereof |
| CN103087082B (en) * | 2011-10-28 | 2014-11-26 | 国家纳米科学中心 | Porphyrin-phthalocyanine pentaplet, preparation method and applications thereof |
| CN113912613A (en) * | 2021-09-23 | 2022-01-11 | 鞍山七彩化学股份有限公司 | Method for preparing halogen substituent phthalocyanine blue and halogen substituent phthalocyanine blue |
| CN113912613B (en) * | 2021-09-23 | 2023-09-01 | 鞍山七彩化学股份有限公司 | Method for preparing halogen substituent phthalocyanine blue and halogen substituent phthalocyanine blue |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101544650B (en) | 2011-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yang et al. | Preparation of magnesium, nitrogen-codoped carbon quantum dots from lignin with bright green fluorescence and sensitive pH response | |
| CN109400899B (en) | Lead coordination polymer and preparation method and application thereof | |
| WO2017201998A1 (en) | Fluorescent compound with sensing function for aniline and o-toluidine gases, and preparation and use of fluorescent sensing thin film | |
| Liu et al. | A novel fluorescence assay based on self-doping biomass carbon dots for rapid detection of dimethoate | |
| CN106542520B (en) | The preparation method of green orange red three fluorescence graphene quantum dot | |
| CN109589989A (en) | ZnIn2S4Nanometer sheet wraps up β-Bi2O3Nucleocapsid Heterogeneous Composite photochemical catalyst and its preparation method and application | |
| CN111548368B (en) | Copper nanocluster with high stability and near-infrared phosphorescence and preparation method thereof | |
| CN107722047A (en) | A kind of double-core Rare Earth Europium Complex luminescent material and its preparation method and application | |
| CN107382982B (en) | dicyanomethylene-4H-pyran derivative and preparation method and application thereof | |
| CN114573544A (en) | Molecular switch with multiple stimulus responses and synthesis method thereof | |
| CN102728850B (en) | Method for preparing high-stability polymer coated nano silver cluster | |
| CN101544650B (en) | Iodo-copper phthalocyanine nano-bar material and synthesizing method thereof | |
| CN108342190B (en) | Nano fluorescent probe for detecting HNO in ratio mode and preparation method and application thereof | |
| CN108586505B (en) | Europium complex red-light material based on two different first ligands and preparation method thereof | |
| 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 | |
| CN101597315B (en) | Organic metal coordination compound gelator and luminous gel composed of same | |
| CN109020828B (en) | Schiff base copper complex and preparation method and application thereof | |
| CN115322262B (en) | Be used for detecting Fe 3+ Dialdehyde cellulose coumarin fluorescent probe and preparation method and application thereof | |
| CN107188801A (en) | Bivalent cupric ion fluorescence probe and Preparation method and use based on tetraphenylethylene ionic complex | |
| CN101240164B (en) | Method for synthesizing sensitive photochromic WO3 nano powder by formaldehyde inducement | |
| CN113717231B (en) | AIE active force-induced light five-membered six-membered heterocyclic platinum complex, and preparation method and application thereof | |
| CN104744208A (en) | Biphenyl-type fluorine-containing liquid crystal monomer as well as catalyst and preparation method thereof | |
| CN104004508A (en) | Preparation method of conductive mixed metal polymer film material | |
| CN103864823A (en) | Cu (I) coordination polymer green light emitting material and synthesis method thereof | |
| Kim et al. | The photophysical behavior of the photochromic naphthopyran derivative having photo-switching ability |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |