CN108440959B - Chiral backbone type azobenzene polymer aggregation and preparation method thereof - Google Patents

Chiral backbone type azobenzene polymer aggregation and preparation method thereof Download PDF

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CN108440959B
CN108440959B CN201810318044.7A CN201810318044A CN108440959B CN 108440959 B CN108440959 B CN 108440959B CN 201810318044 A CN201810318044 A CN 201810318044A CN 108440959 B CN108440959 B CN 108440959B
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chiral
aggregation
azobenzene polymer
polysilane
backbone
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CN108440959A (en
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张伟
陈海玲
朱秀林
朱健
张正彪
周年琛
潘向强
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Suzhou University
Nantong Textile and Silk Industrial Technology Research Institute
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Suzhou University
Nantong Textile and Silk Industrial Technology Research Institute
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/093—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2483/04—Polysiloxanes

Abstract

The present invention relates to a kind of chiral backbone type azobenzene polymer aggregations and preparation method thereof, and concrete operations are as follows: with the 1 × 10 of pipettor difference draws equal amounts‑5 The chiral polysilane of M and the chloroform soln of azobenzene polymer are added in the cuvette containing stirrer, add a certain amount of good solvent chloroform, after stirring 2 minutes, cuvette is moved on desktop, a certain amount of poor solvent methanol is added along wall again, 2 minutes lightly are stood after turned upside down 8 times, and chiral backbone type azobenzene polymer aggregation has been made.The present invention to prepare there is chiral azobenzene polymer aggregation to provide a kind of new method, after finding suitable good solvent and poor solvent, by regulating and controlling the volume ratio of good solvent and poor solvent, it is successfully prepared the isomery aggregation of backbone chain type azobenzene polymer.The aggregation that the azobenzene polymer with single chiral has just been obtained after chiral polysilane is decomposed completely with recycling ultraviolet selective.

Description

Chiral backbone type azobenzene polymer aggregation and preparation method thereof
Technical field
The present invention relates to a kind of methods for preparing polymer aggregation of chemical field, and in particular to chiral backbone Type azobenzene polymer aggregation and preparation method thereof.
Background technique
In macromolecule research field, there is the aggregation of specific function using the preparation of intermolecular active force and regulate and control it Property is a huge challenge.The performance of aggregation determines by the degree of order of the molecule in assembly and ordered state, therefore The assembling for how controlling pi-conjugated molecule, the structure for regulating and controlling the aggregation of response are to prepare the basis of new material.
Because substance with optical activation plays huge effect, always section in nature and life entity Grind the research hotspot of worker.Chiral solvent revulsion is exactly to prepare the common method of chiral material, although solving previous benefit The chiral complicated synthesis step to be faced of polymer is obtained with chiral monomer polymerization and achiral monomers Asymmetric Polymerization method The problems such as with expensive chiral catalyst, but for preparing the simple chiral aggregation that has, still there is certain to lack It falls into.Such as chiral limonene is commonly used to be filled with its chirality of induction with achiral polymer group, but begin in such aggregation There is the limonene molecules for being not easy to remove eventually, can generate certain obstruction for actual production utilization.
Summary of the invention
The purpose of the present invention is to provide a kind of new methods for preparing azobenzene polymer aggregation, have also widened induction The road of azobenzene polymer chirality.
The specific technical solution that the present invention uses is as follows:
A kind of preparation method of chiral backbone type azobenzene polymer isomery aggregation, includes the following steps, will under stirring Backbone chain type azobenzene polymer solution, chiral polysilane solution are added in reactor, then sequentially add good solvent, bad molten Agent stands after inversion processing, obtains chiral backbone type azobenzene polymer isomery aggregation.
A kind of preparation method of the equal aggregation of chiral backbone type azobenzene polymer, includes the following steps, under stirring, will lead Chain azobenzene polymer solution, chiral polysilane solution are added in reactor, then sequentially add good solvent, poor solvent, It is stood after inversion processing, obtains chiral backbone type azobenzene polymer isomery aggregation；Then treatment with ultraviolet light chiral backbone is used Type azobenzene polymer isomery aggregation obtains the equal aggregation of chiral backbone type azobenzene polymer.
A kind of preparation method of chiral backbone type azobenzene polymer aggregation forerunner's system, includes the following steps, stirring Under, backbone chain type azobenzene polymer solution, chiral polysilane solution are added in reactor, good solvent, no is then sequentially added Good solvent obtains chiral backbone type azobenzene polymer aggregation forerunner's system.
The present invention is acted on using chiral polysilane and aggregation inducing of the backbone chain type azobenzene polymer in binary solvent To the isomery aggregation with chiral response, with fast selective can be decomposed completely by the irradiation of the ultraviolet light at 313 nm Fall chiral polysilane to obtain the aggregation of the simple azobenzene polymer with single chiral, this is one relatively new Unique method；It the advantage is that chiral polysilane is rigid rodlike chiral structure, there is very strong optical activity, it can and can only By the ultraviolet photodegradation at 313 nm, can be easily made using suitable preparation condition of the invention with chiral idol Pyridine polymer aggregation.Since azobenzene is photosensitive chromophore, the compound with azobenzene chromophore possesses rich The property of rich spectroscopy and optical physics, therefore the technology of preparing of the aggregation of the polymer containing azobenzene group can be applied to Every aspect of production and living, such as luminescent material, electronic device etc., storage medium material etc..
In above-mentioned technical proposal, solvent is chloroform, chiral polysilane solution in backbone chain type azobenzene polymer solution Middle solvent is chloroform.
In above-mentioned technical proposal, good solvent refers to the solvent that can dissolve backbone chain type azobenzene polymer, chiral polysilane, Chloroform, tetrahydrofuran, 1,2- dichloroethanes, toluene etc., preferably chloroform；Poor solvent, which refers to, cannot dissolve main chain The solvent of type azobenzene polymer, chiral polysilane, methanol, n-hexane, isopropanol, ethyl alcohol, hexamethylene etc., preferably small molecule Alcohol, such as methanol.
In above-mentioned technical proposal, the concentration of backbone chain type azobenzene polymer solution is 1 × 10-5 M, chiral polysilane solution Concentration be 1 × 10-5 M；Concentration is to repeat unit concentration.
In above-mentioned technical proposal, backbone chain type azobenzene polymer is the copolymerization for containing 9,9- dioctyl fluorene and azobenzene group Object, chiral polysilane be (S)-(-)-/(R)-(+) -2- methyl butyl-n-hexyl polysilane；Backbone chain type azobenzene polymer Molecular weight (M n) it is 23000 ~ 24000g/mol；Chiral polysilane be rodlike chiral structure, molecular weight (M n) it is 20000 ~ 24000 g/mol。
In above-mentioned technical proposal, backbone chain type azobenzene polymer and chiral polysilane equimolar amounts.
In above-mentioned technical proposal, being inverted number of processes is 2~10 times；Time of repose is 1~5 minute.The purpose of stirring is In order to which chiral polysilane and azobenzene polymer preferably interact, the purpose of standing is to allow the more preferable real estate of aggregation It is raw；The preparation of aggregation can be carried out in normal experimental situation, not special requirement of experiment.
In above-mentioned technical proposal, the totality of backbone chain type azobenzene polymer solution, chiral polysilane solution and good solvent The long-pending volume ratio with poor solvent is (2.2: 0.8)~(0.3: 2.7), may detect that chiral signal within the scope of this, and It is preferred that 2: 1 when is strongest chiral signal；It will be obtained not after the volume ratio of good solvent and poor solvent goes beyond the scope To aggregation.
Above-mentioned technical proposal can be expressed as follows: preparing repetitive unit concentration in advance is 1 × 10-5 The two kinds of polymer of M Chloroform soln, a kind of polymer are the backbone chain type copolymer F8Azo containing 9,9- dioctyl fluorene and azobenzene group；It is another Kind be (S)-(-)-/(R)-(+) -2- methyl butyl-n-hexyl polysilane (S/R- PSi).0.15 mL is drawn respectively containing F8Azo WithS/RThe chloroform soln of-PSi adds the good solvent of 1.7 mL in the cuvette of 3 mL for being built-in with stirring magneton Chloroform, turned upside down, which is once placed on magnetic stirring apparatus, stirs 2 min.Cuvette is placed on desktop after 2 minutes, edge The poor solvent methanol of 1 mL is added in the inner wall of cuvette, 2 min is stood after being gently inverted 8 times up and down on the table to be formed Stable chiral backbone type azobenzene polymer isomery aggregation.
Whether aggregation is successfully prepared, one is by visually being observed, it can be seen that being suspended in solution under light The aggregate particle of the inside, but this method is just not suitable for very small aggregation, second is that with circular dichroism instrument into Row detection thus whether illustrating the formation of aggregation to a certain extent.Chiral backbone type azo is detected with circular dichroism instrument Then the chirality of benzene polymer isomery aggregation with the ultraviolet selective at 313 nm decomposes chiral polysilane completely, from And obtain uniform there is chiral F8Azo collective, the i.e. equal aggregation of chiral backbone type azobenzene polymer.
Due to practicing for above-mentioned technical proposal, the present invention has the advantage that compared with prior art
The present invention utilizes for the first time can be gathered under 313 nm action of ultraviolet light by the selective chiral polysilane decomposed completely Collection induction preparation has the aggregation of the backbone chain type azobenzene polymer of chiral response；Used chiral polysilane in the present invention It can selectively be decomposed completely after 15 S of ultraviolet light for 313 nm that light intensity is 190.0 μ W/cm2, and And since illumination has promoted the ordered arrangement of aggregation, the chiral of the azobenzene being induced not only enhances without disappearing instead.This Invention overcomes bad the drawbacks of completely removing limonene molecule after traditional chiral limonene induced chirality, proves chirality Macromolecular can also induce the chirality of achirality polymer, and easily be divided completely by the ultraviolet selective at 313 nm Solution.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic resonance of the copolymer F8Azo containing 9,9- dioctyl fluorene and azobenzene group in embodiment one Spectrogram；
Fig. 2 is the GPC elution curve of the copolymer F8Azo containing 9,9- dioctyl fluorene and azobenzene group in embodiment one Figure；
Fig. 3 be chiral polysilane in embodiment one (S-/R- PSi) or F8Azo aggregation circular dichroism figure；
Fig. 4 is F8Azo- in embodiment twoS- PSi and F8Azo- RThe circular dichroism figure of-PSi isomery aggregation；
Fig. 5 is the F8Azo- in embodiment two under different solvents volume ratioS- PSi and F8Azo- R- PSi isomery aggregation At 475 nmg CDIt is worth change curve；
Fig. 6 is to apply F8Azo- in example threeSThe circular dichroism figure of-PSi isomery aggregation before and after 10 s of ultraviolet light irradiation；
Fig. 7 is to apply F8Azo- in example three RCircular dichroism of-PSi isomery the aggregation before and after 10 s of ultraviolet light irradiation Figure；
Fig. 8 is to apply F8Azo- in example threeSThe DLS figure of-PSi isomery aggregation before and after 15 s of ultraviolet light irradiation.
Specific embodiment
Following test equipment and condition are used in the embodiment of the present invention:
Chemical reagent used in the present embodiment is the pure chloroform of the order of spectrum (Dojindo) and methanol (Dojindo), Cuvette used is the cuvette for the SQ rank that outer diameter is the mm of 10 mm × 10.
Gel permeation chromatography (GPC): it is measured using Waters1515 gel permeation chrommatograph, uses differential refraction detector (RI2414), the molecular weight ranges of HR1, HR2 and HR4 pillar are 100-500000 Da, with tetrahydrofuran (THF) for mobile phase, Flow velocity is 1.0 mL/min, is tested at 30 DEG C, with polystyrene standards or polymethyl acrylate standard specimen to polymer Molecular weight is demarcated；
Nuclear magnetic resonance spectroscopy (1H-NMR): Bruker 300MHz nuclear magnetic resonance spectrometer is used, with CDCl3(deuterated chloroform) is molten Agent, TMS(tetramethylsilane) it is internal standard, it measures at room temperature；
Circular dichroism instrument (CD): Japanese JASCO company JASCO-725 type, determination condition: 100 nm/ of scanning speed Min, wave-length coverage: 230 ~ 700 nm, wavelength accuracy: ± 0.1 nm (230 ~ 700 nm), bandwidth: 2 nm, response time 2 Second, muting sensitivity is tested under room temperature.Ultra-violet absorption spectrum synchronization gain under the test conditions above；
Light source: the high-pressure mercury of 500 W of Tokyo USHIO company Optical ModuleX SX-UID502HUV type Lamp；
Filter plate: the ultraviolet light of narrow distribution is obtained using the filter plate (Sigma KoKi, Shanghai, China) of 313 nm.
Embodiment one
(1) pretreatment of backbone chain type azobenzene polymer
The synthetic copolymer containing 9,9- dioctyl fluorene and azobenzene group of the prior art is dissolved with chloroform After filter, remove substance insoluble in good solvent chloroform, concentration clear liquid obtains crude product, chloroform dissolve after in methanol Middle sedimentation filters after standing and obtains polymer, is placed in 30 DEG C of vacuum drying ovens dry 12 h to get the master required to the present invention Chain azobenzene polymer F8Azo is used for following experiment.
Relevant nuclear magnetic resonance spectroscopy (Fig. 1) and gel permeation chromatography GPC(Fig. 2 then have been carried out to the polymer) it surveys Examination, very can clearly find out from the nucleus magnetic hydrogen spectrum of Fig. 1 characteristic peak at 7.60-8.20 ppm it is corresponding be polymer The chemical shift of hydrogen in structure in fluorenes unit and azo-benzene units on phenyl ring, corresponding characteristic peak at 2.13 ppm is poly- Close the chemical shift in object with the unit 9 upper two nearest methylene connected, methylene and methyl on remaining alkyl chain Chemical shift present in 0.50-1.40 ppm.Its number-average molecular weight is measured with gel permeation chromatography GPCMn =23900 Curve in Da, molecular weight distribution PDI=1.61(Fig. 2).
(2) weigh respectively the F8Azo and 0.18 mg of 0.57 mg chiral polysilane ((S)-(-)-/(R)-(+) -2- first Base butyl-n-hexyl polysilane), the pure chloroform solvent of the order of spectrum for being separately added into 5 mL is respectively made into repetitive unit concentration It is 1.0 × 10-5The solution of M, heating make it completely dissolved.
(3) preparation of chiral polysilane and the equal aggregation of F8Azo
Drawing 0.15 mL concentration respectively is 1.0 × 10-5The F8Azo of M,SOrRThe chloroform soln of-PSi is in being built-in with In the cuvette of small stirrer, the good solvent chloroform of 1.85 mL is added, will be compared with after magnetic stirrer 2 minutes Color ware moves on desktop, and the poor solvent methanol of 1.0 mL is added along the inner wall of cuvette, gently stands 2 after turned upside down 8 times Minute, the aggregation liquid solution of azobenzene or chiral polysilane has been made.
In the system, it can be assembled by the non-covalent bond effect power between chiral polysilane and azobenzene polymer and be lured The chirality of azobenzene polymer is led, then chirality can be detected using circular dichroism, can also proved to a certain extent Whether the formation of chiral aggregations body.Three obtained (F8Azo, S-Psi, R-PSi) assembles survey of the liquid solution through circular dichroism instrument Examination obtains the circular dichroism figure such as Fig. 3, can find out the UV absorption region of F8Azo in 350 nm-550 from the solid line in figure Nm, and chiral expression is not seen in corresponding region, and two polysilanes all have apparent chiral signal, and are almost in Mirror image corresponding relationship.
Two F8Azo- of embodimentS/RThe preparation of-PSi isomery aggregation
(1) it is 1.0 × 10 that 0.15 mL concentration is sequentially added into the cuvette for being built-in with small stirrer-5The F8Azo's of M Chloroform soln and 0.15 mL concentration are 1.0 × 10-5M'sSOrRThe chloroform soln of-PSi adds 1.7 mL's Good solvent chloroform, magnetic stirrer moved to cuvette on desktop after 2 minutes, and the inner wall along cuvette is added 1.0 The poor solvent methanol of mL obtains chiral backbone type azobenzene polymer aggregation forerunner's system；Again gently after turned upside down 8 times 2 minutes are stood, F8Azo- has been madeS- PSi or F8Azo- RThe isomery aggregation of-PSi；Backbone chain type azobenzene polymer solution, The volume ratio of the total volume and poor solvent of chiral polysilane solution and good solvent is 2: 1.
Fig. 4 is the CD-UV spectrogram that circular dichroism instrument detects isomery aggregation, it can be seen from the figure that through Overbunching induction, chiral polysilane success, can from apparent chiral signal from 350 nm-550 nm induction of the chirality of F8Azo To knowR- PSi induces F8Azo to generate right hand chirality, andSIt is lefthanded that-PSi induces F8Azo to generate；And by calculating, hair At existing 475 nmg CDValue up to 91.24 × 10-4(R- PSi), -105.3 × 10-4(S- PSi).
(2) according to the method for preparing isomery aggregation in embodiment two (1), by backbone chain type azobenzene polymer solution, hand The total volume of property polysilane solution and good solvent chloroform is from poor solvent methanol according to different volume ratios (2.2: 0.8) ~(0.3: 2.7) prepares isomery aggregation F8Azo-S/R- PSi, come explore the good solvent volume ratio different with poor solvent for The influence of aggregation inducing azobenzene chirality.It is 475 in different volumes than the UV absorption region where lower azobenzene such as Fig. 5 At nmg CDThe change curve of value, from the variation tendency of curve it can be concluded that being preferably in a proportion of 2.0:1.0, aggregation inducing Effect it is best.
Embodiment three obtains the simple F8Azo aggregation with chirality using ultraviolet photodegradation chirality polysilane
F8Azo- is prepared respectively according to the step of embodiment twoS- PSi or F8Azo- RThe isomery aggregation of-PSi, benefit With circular dichroism instrument come the chirality of detection of aggregation body, then with the ultraviolet source that the wavelength put up is 313 nm to this F8Azo-S- PSi or F8Azo- RThe isomery aggregation of-PSi carries out circular dichroism test after irradiating 10 s respectively again.Point The CD-UV variation diagram (Fig. 6, Fig. 7) of the ultraviolet light irradiation front and back isomery aggregation at 313 nm is not obtained, it can be seen that ultraviolet light After only irradiating 10 s, the chiral signal peak and ultraviolet absorption peak of the chiral polysilane at 300-350 nm almost weaken to disappearance, Illustrate that chiral polysilane is substantially decomposed to finish, obtains the equal aggregation of chiral backbone type azobenzene polymer.Meanwhile 350- F8Azo at 550 nm be induced chirality do not disappear not only, chiral signal significantly enhances instead, this should be by In illumination aggregation is arranged more orderly.
In order to prove whether to have obtained the simple F8Azo aggregation with chirality, the ultraviolet light pair at 313 nm is utilized The F8Azo- prepared in advanceS- PSi isomery aggregation, which successively irradiates 5 s, 10 s, 15 s(, adds up same isomery aggregation Irradiation time), chiral and ultraviolet situation of change is detected using circular dichroism instrument after having shone every time.By being calculated It is corresponding in table 1g CDValue, after can be seen that 5 s of ultraviolet light irradiation from the data variation in tableg CDValue just has clearly Variation, illustrate that 5 s of ultraviolet light irradiation can decompose most chiral polysilane.And accumulative irradiation 10 s and 15 of ultraviolet light At 320 nm wavelength after sg CDIt is worth essentially the same, polysilane divides completely after illustrating 10 s of ultraviolet light irradiation of 313 nm Solution.Fig. 8 is dynamic light scattering diagram (DLS), has recorded the variation for the aggregate particle size that 313 nm are irradiated before and after 15 s, can from figure After finding out the complete chiral polysilane of ultraviolet photodegradation, the partial size of aggregation becomes smaller, and illustrates that polysilane is just broken off, this It is able to demonstrate that after ultraviolet light irradiation, we have obtained the simple azobenzene aggregation with chirality.
1 F8Azo- of tableS- PSi isomery aggregation is corresponding after ultraviolet light successively irradiates 5 s, 10 s, 15 sg CDIt is worth number According to table
Above-mentioned result can sufficiently prove that achiral backbone chain type azobenzene polymer is in the aggregation with chiral polysilane It is formd under inducing action with chiral aggregation, and is obtained after the chiral polysilane of the complete decomposition of ultraviolet selective Simple chiral azobenzene aggregation.Chirality azobenzene aggregation prepared by the present invention is situated between in photoswitch, electronic device, storage The fields such as material and liquid crystal material all have huge potential use.

Claims (4)

1. a kind of preparation method of the equal aggregation of chiral backbone type azobenzene polymer, includes the following steps, under stirring, by main chain Type azobenzene polymer solution, chiral polysilane solution are added in reactor, then sequentially add good solvent, poor solvent, It is stood after setting processing, obtains chiral backbone type azobenzene polymer isomery aggregation；Then treatment with ultraviolet light chiral backbone type is used Azobenzene polymer isomery aggregation obtains the equal aggregation of chiral backbone type azobenzene polymer；The backbone chain type azobenzene is poly- Solvent is chloroform in polymer solution, and solvent is chloroform in chiral polysilane solution；Backbone chain type azobenzene polymer is molten The concentration of liquid is 1 × 10-5 M, the concentration of chiral polysilane solution are 1 × 10-5 M；Backbone chain type azobenzene polymer and chirality are poly- Silane equimolar amounts；The good solvent includes chloroform, tetrahydrofuran, 1,2- dichloroethanes, toluene；The poor solvent packet Include methanol, n-hexane, isopropanol, ethyl alcohol, hexamethylene；Good solvent, poor solvent volume ratio be (2.2: 0.8)~(0.3: 2.7)；The backbone chain type azobenzene polymer is the copolymer for containing 9,9- dioctyl fluorene and azobenzene group, chiral polysilane For (S)-(-)-/(R)-(+) -2- methyl butyl-n-hexyl polysilane；The molecular weight of backbone chain type azobenzene polymer be 23000 ~ 24000g/mol；Chiral polysilane is rodlike chiral structure, and molecular weight is 20000 ~ 24000 g/mol.
2. preparation method according to claim 1, which is characterized in that being inverted number of processes is 2~10 times；Time of repose is 1~5 minute.
3. the preparation method according to claim 1, which is characterized in that the wavelength of ultraviolet light is 313 nm.
4. the equal aggregation of chiral backbone type azobenzene polymer of preparation method preparation according to claim 1.
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