CN101570527B - Solid magnetism and fluorescence organic compound 3-chlorin bi-indene isolactone and synthetic method - Google Patents
Solid magnetism and fluorescence organic compound 3-chlorin bi-indene isolactone and synthetic method Download PDFInfo
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Abstract
The present invention discloses solid magnetism and fluorescence difunctional organic compound and a synthetic method thereof. The present invention takes 3-chlorin phthalic anhydrideand butane diacid as raw materials to synthesize a compound, wherein the structural formula of which is as follows. The synthetic method is as follows: the 3- chlorin phthalic anhydride and butane diacid are blended for preparing a midbody used for synthesizing the compound; and the midbody is catalyzed by sodium alkoxide to synthesize the compound. The compound provided by the invention is the solid magnetism and fluorescence organic compound, has the difunctional of fluorescence and paramagnetism, can be applied to the fluorescence labeling and distinguishing field, and fields such as new generation stored information material, separation material, light broadband microwave absorption, magnetic sensors, small loss and high frequency micro-wave commutation devices, magnetic sealing devices, magnetic shades, magnetic separation, micro-wave communication, etc.
Description
[technical field]:
The invention belongs to the organic materials synthesis technical field, particularly a kind of have fluorescence and bifunctional organic compound of magnetic and a synthetic method thereof.
[background technology]:
Organic magnet is the frontier branch of science of a multidisciplinary intersection, it relates to subjects such as organic and inorganic, organo-metallic, polymkeric substance, physical chemistry, Condensed Matter Physics, belongs to main research and has magnetic, photoconduction, electricity and the design of the molecular system of specific physical character, synthetic and application such as lead
[1]Emerging research field---the molecular solid (Molecular solid) of multidisciplinary intersection.For a long time, people think that an organic/inorganic substance just has above these character, and organism then is considered to diamagnetic material or electrical insulator.Up to recently, all proved in the theoretical and test some special organic materials through overdoping or with other organic or inorganic ionic bond after, can show magnetic or change conductor into even superconductor.Phase at the beginning of the sixties in last century, MeConnell
[2]Proposition is encouraging people to make unremitting effort for seeking such system based on the theory prophesy that the ferro-magnetic of molecular system may exist.At present, this field relates to organic semiconductor, organic photoconductor, organic conductor and superconductor, conductive polymers, organic non linear optical material, new-type functional material such as Organic Ferromagnet and relevant electronic processes.Compare with other materials research, though the research of Organic Ferromagnet is started late, researchdevelopment has in recent years fully shown the development potentiality in this field.
First molecule ferro-magnetic is by ferrocene [Fe (Cp
*)
2] charge-transfer complex that forms with TCNE (TCNE)
[3]: [Fe (η
5-C
5Me
5)
2]
+[TCNE]
-, be that people such as Miller was in report in 1986; Meanwhile, Kahn
[4]Reported MnCu (pbaOH) (H
2O)
3Have ferromegnetism, this has just announced the ferromagnetic birth of molecule.In recent years, the research of magneticsubstance has obtained challenging progress, Verdaguer again
[5,6]With people such as Epstein
[7]Reported the V (TCNE) of Tc respectively up to 340K
21/2 (CH
2Cl
2) and [Cr (CN) of 500K
6]
Q-V
P+The molecule ferro-magnetic.
Phase at the beginning of the sixties in last century, scientists has just begun the theoretical investigation of Organic Ferromagnet, but progress is very slow.1963, McConnell
[2]The possibility of Organic Ferromagnet has been proposed.Nineteen sixty-eight Mataga
[8], Ovchinnikov in 1978
[9]Proved its possibility again theoretically.Up to USSR (Union of Soviet Socialist Republics) scientist Ovchinnikov in 1987
[10]Reported first Poly-BIPO[1, and 3-bis (2,2,6,6-tetramethyl-3-piperidyl-1-oxyl)-Butadiyne] had since macroscopical ferromegnetism, the research of organic magnet is just really come out.1991, first Organic Ferromagnet based on C, H, O, four kinds of elements of N just was synthesized out
[11], the organic compound that people is recognized contain N, O free radical also is the ferromagnetic a kind of effective ways of preparation molecule
[12]
Traditional biological label method comprises radioisotope method and fluorescence labeling method.Radio isotope can produce radiation to organism, environment is polluted, and radio isotope all has the transformation period of himself, signal can be more and more a little less than, so this method is abandoned by people now gradually.And the signal to noise ratio height, the fluorescence labeling technology that sensitivity is good has been widely used in biological and medical aspect, plays an important role in fields, life science forward position such as biochip, protein analysis, dna sequencing, fluoroimmunoassay, fluidic cell measurement, clinical analysis of diagnosis and treatments
[13-14]Therefore, novel fluorescent compound is synthetic significant.
[summary of the invention]:
The object of the invention provides a kind of novel molecular solid paramagnetism and fluorescent dual-function organic compound and synthetic method thereof.
Molecular solid paramagnetism provided by the invention and fluorescent dual-function organic compound, its structural formula is:
The synthetic method of above-mentioned compound comprises:
Synthetic route:
Concrete synthesis step is as follows:
The first, intermediate is synthetic
Thermometer is being housed, in reflux exchanger and the churned mechanically four-hole bottle, is adding 3-chloro-phthalic anhydride and Succinic Acid (mol ratio is 1: 1～2), be warming up to 210 ℃.Start stirring, (mol ratio of potassium acetate and 3-chloro-phthalic anhydride is 0.2～0.35: 1), 210 ℃ were reacted 2～4 hours to add potassium acetate.Be cooled to 100 ℃ then, add hot water and import water vapour.Form broken particle up to reaction product, filter, use the hot water wash product, drying is boiled to remove resinous impurities with ethanol.Refilter, with ethanol wash elutant colourless till, drying, little reddish yellow powder, be the intermediate that is used for synthetic described compound.
The second, described compound synthesizes
Thermometer is being housed, in reflux exchanger and the churned mechanically four-hole bottle, intermediate is being suspended with methyl alcohol, be warming up to 60 ℃, under mechanical stirring, the sodium methoxide solution that drips (mol ratio of intermediate and sodium methylate is 1: 2～3) was with mixed-liquor return reaction 0.5～1.5 hour.Cooling is filtered, and it is colourless to effluent liquid to wash the black product with dehydrated alcohol.With aqueous suspension black product and boil, filtered while hot, it is colourless to elutant to continue the water flush cake, obtains red as fire look solid, promptly described compound.
The structural characterization data:
1HNMR：δ(ppm)7.07-7.84(m，6H)13.48-15.16(m，2H)
IR:(KBr, diffuse-reflectance, cm
-1) 3075.15,1630.37,1574.81,1482.06,1348.01,1096.88MS:m/z 358 (M
+)
ESR test result: g=2.003.
Advantage of the present invention and positively effect:
Organic compound provided by the invention is a kind of novel difunctional organic compound, has fluorescence and paramagnetism is difunctional.
Solid magnetic provided by the invention and fluorescent dual-function organic compound can be used for fluorescent mark, identification field; And the manufacturing of organo-metallic material, can be applied to high canned data material of new generation, isolated material, lightweight wide-band microwave absorption agent, magneticsensor, low-loss high-frequency microwave communication device, magnetic seal device, fields such as magnetic shielding, magnetic separation, microwave communication.
[description of drawings]
Fig. 1 is the fluorogram (in the methyl alcohol) of compound of the present invention;
Fig. 2 is the ESR spectrogram of compound of the present invention.
[embodiment]:
Embodiment 1:
Thermometer is being housed, in reflux exchanger and the churned mechanically 250mL four-hole bottle, is adding 3-chloro-phthalic anhydride 30.5g (0.167mol) and Succinic Acid (being adding in 1: 1 in molar ratio), be warming up to 210 ℃.Start stirring, add potassium acetate (mol ratio of potassium acetate and 3-chloro-phthalic anhydride is 0.2: 1), 210 ℃ were reacted 2.5 hours.Be cooled to 100 ℃ then, add hot water and import water vapour.Form broken particle up to reaction product, filter, use the hot water wash product, drying is boiled to remove resinous impurities with ethanol.Refilter, with ethanol wash elutant colourless till, drying, little reddish yellow powder 18.3g, be the intermediate that is used for synthetic compound of the present invention.
Thermometer is being housed, in reflux exchanger and the churned mechanically 250mL four-hole bottle, the 18.0g intermediate is being suspended with methyl alcohol, be warming up to 60 ℃, under agitation, the sodium methoxide solution that drips (mol ratio of intermediate and sodium methylate is 1: 2) was with mixed-liquor return reaction 1 hour.Cooling is filtered, and it is colourless to effluent liquid to wash the black product with dehydrated alcohol.With aqueous suspension black product and boil, filtered while hot, it is colourless to elutant to continue the water flush cake, obtains red as fire look solid, compound 3.3g promptly of the present invention.Yield 18.3%.M.p.298 ℃ (decomposition).
Embodiment 2:
Thermometer is being housed, in reflux exchanger and the churned mechanically 250mL four-hole bottle, is adding 3-chloro-phthalic anhydride 30.5g (0.167mol) and Succinic Acid (mol ratio is 1: 1.5), be warming up to 210 ℃.Start stirring, add potassium acetate (mol ratio of 3-chloro-phthalic anhydride and potassium acetate is 1: 0.3), 210 ℃ were reacted 2.5 hours.Be cooled to 100 ℃ then, add hot water and import water vapour.Form broken particle up to reaction product, filter, use the hot water wash product, drying is boiled to remove resinous impurities with ethanol.Refilter, with ethanol wash elutant colourless till, drying, little reddish yellow powder 15.6g, be the intermediate that is used for synthetic compound of the present invention.
Thermometer is being housed, in reflux exchanger and the churned mechanically 250mL four-hole bottle, the 15.0g intermediate is being suspended with methyl alcohol, be warming up to 60 ℃, under agitation, the sodium methoxide solution that drips (mol ratio of intermediate and sodium methylate is 1: 2) was with mixed-liquor return reaction 0.5 hour.Cooling is filtered, and it is colourless to effluent liquid to wash the black product with dehydrated alcohol.With aqueous suspension black product and boil, filtered while hot, it is colourless to elutant to continue the water flush cake, obtains red as fire look solid, compound 3.0g promptly of the present invention.Yield 20.0%.M.p.298 ℃ (decomposition).
Embodiment 3:
Thermometer is being housed, in reflux exchanger and the churned mechanically 250mL four-hole bottle, is adding 3-chloro-phthalic anhydride 30.5g (0.167mol) and Succinic Acid (mol ratio is 1: 2), be warming up to 210 ℃.Start stirring, add potassium acetate (mol ratio of 3-chloro-phthalic anhydride and potassium acetate is 1: 0.3), 210 ℃ were reacted 2.5 hours.Be cooled to 100 ℃ then, add hot water and import water vapour.Form broken particle up to reaction product, filter, use the hot water wash product, drying is boiled to remove resinous impurities with ethanol.Refilter, with ethanol wash elutant colourless till, drying, little reddish yellow powder 17.8g, be the intermediate that is used for synthetic compound of the present invention.
Thermometer is being housed, in reflux exchanger and the churned mechanically 250mL four-hole bottle, the 17.0g intermediate is being suspended with methyl alcohol, be warming up to 60 ℃, under agitation, the sodium methoxide solution that drips (mol ratio of intermediate and sodium methylate is 1: 2) was with mixed-liquor return reaction 1.5 hours.Cooling is filtered, and it is colourless to effluent liquid to wash the black product with dehydrated alcohol.With aqueous suspension black product and boil, filtered while hot, it is colourless to elutant to continue water flush cake for some time, obtains red as fire look solid, compound 2.6g promptly of the present invention.Yield 15.3%.M.p.298 ℃ (decomposition).
Photoluminescent property is measured
The fluorescent characteristic of compound of the present invention (in the methyl alcohol) sees Table 1:
The fluorescent characteristic of table 1, compound of the present invention
The test of ESR magnetic
Test condition: F=9.849GHz, P=2.002mW, Sweep Time=83.886s
The ESR spectrum parameter g=2.003 of compound of the present invention.
. reference
[1]Nakamura，T.et?al.Nature?1998，394：159
[2]McConnell，H.M.J.Chem.Phys.1963，39：1910
[3]Miller，J.S.et?al.J.Chem.Soc.Chem.Commun.1986，1026
[4]Rei，Y.et?al.J.Am.Chem.Soc.1986，108：7428
[5]Ferlays，et?al.Nature?1995，378：701
[6]Mallah.T.et?al.Science?1993，262：1554
[7]Manriquez，J.M.et?al.Science?1991，252：1415
[8]Mataga，N.Theor.Chim.Acta.1968，10：372
[9]Ovchinnikov，A.A.Theor.Chim.Acta.1978，47：297
[10]Korshak，Y.V.et?al.Nature?1987，326：370
[11]Turek，P.et?al.Chem.Phys.Lett.1991，180：327
[12]Li，Y.L.et?al.Chem.Phys.Lett.1997，265：361
[13]Schobel?U，Egelhaaf?H?J，.Brechl?A.Bioconjugate?Chem.，1999，10(6)：1107-1114
[14]Mujumbdar?S?R，MujumbdarRB，Waggoner?C?M.Bioconjugate?Chem.，1996，7(3)：356-362。
Claims (2)
1. solid magnetic and fluorescent dual-function organic compound, the compound that is shown below:
2. the synthetic method of the described compound of claim 1 is characterized in that comprising:
Synthetic route:
Concrete synthesis step is as follows:
The first, intermediate is synthetic
Thermometer is being housed, in reflux exchanger and the churned mechanically four-hole bottle, be that 1: 1～2 ratio adds 3-chloro-phthalic anhydride and Succinic Acid in molar ratio, be warming up to 210 ℃, start stirring, add potassium acetate, the mol ratio of potassium acetate and 3-chloro-phthalic anhydride is 0.2～0.35: 1,210 ℃ of reaction 2～4 hours, be cooled to 100 ℃ then, add hot water and import water vapour, form broken particle, filter up to reaction product, use the hot water wash product, drying is boiled to remove resinous impurities with ethanol, refilters, with ethanol wash elutant colourless till, drying gets little reddish yellow powder, is the intermediate that is used for the synthetic described compound of claim 1;
The second, the described compound of claim 1 is synthetic
Thermometer is being housed, in reflux exchanger and the churned mechanically four-hole bottle, intermediate is suspended with methyl alcohol, be warming up to 60 ℃, under agitation, the sodium methoxide solution that drips, the mol ratio of intermediate and sodium methylate was 1: 2～3, with mixed-liquor return reaction 0.5～1.5 hour, cooling, filter, it is colourless to effluent liquid to wash the black product with dehydrated alcohol, with aqueous suspension black product and boil, filtered while hot, it is colourless to elutant to continue the water flush cake, obtains red as fire look solid, is the described compound of claim 1.
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| CN103613569A (en) * | 2013-12-11 | 2014-03-05 | 天津理工大学 | Fluorescent organic compound 4-chloroindene lactone and synthetic method thereof |
| CN103613572A (en) * | 2013-12-11 | 2014-03-05 | 天津理工大学 | Fluorescent organic compound indene lactone and synthetic method thereof |
| CN103613571A (en) * | 2013-12-11 | 2014-03-05 | 天津理工大学 | Fluorescent organic compound 4-methyl indene lactone and synthetic method thereof |
| CN103613570A (en) * | 2013-12-11 | 2014-03-05 | 天津理工大学 | Fluorescent organic compound 3-chloroindene lactone and synthetic method thereof |
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| CN1601780A (en) * | 2004-10-26 | 2005-03-30 | 中国科学院长春应用化学研究所 | Mfg method of fall carrier capture structure organic LED |
| CN1736998A (en) * | 2004-05-19 | 2006-02-22 | 陕西师范大学 | Populin-6-sulfonic acid sodium synthesis method and uses in preparaing photoluminescent material |
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| CN1736998A (en) * | 2004-05-19 | 2006-02-22 | 陕西师范大学 | Populin-6-sulfonic acid sodium synthesis method and uses in preparaing photoluminescent material |
| CN1601780A (en) * | 2004-10-26 | 2005-03-30 | 中国科学院长春应用化学研究所 | Mfg method of fall carrier capture structure organic LED |
Non-Patent Citations (1)
| Title |
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| 李旭等.有机光致变色自由基化合物研究进展.《有机化学》.2007,第27卷(第6期),696-702. * |
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