CN104946241B - One-dimensional organic semiconductor nanotube and its preparation method and application - Google Patents
One-dimensional organic semiconductor nanotube and its preparation method and application Download PDFInfo
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Abstract
The present invention relates to a kind of one-dimensional organic semiconductor nanotube and preparation method thereof and its application in terms of fluorescence quantum yield is greatly improved.Described one-dimensional organic semiconductor nanotube is the imide derivative by two ends with Asymmetrical substitute base, is obtained by the π π interaction self assembly between described acid imide.Described one-dimensional organic semiconductor nanotube drops in different substrate surfaces after being dispersed through in poor solvent, and nanotube spontaneous can be combined into compact arranged nanotube bundle.Owing to energy can be occurred between closelypacked nanotube to shift, when the increasing number of nanotube bundle, when bundle diameters increases, energy transfer is corresponding to be strengthened, making fluorescence quantum yield that (by 21% bring up to 54%) is greatly improved, fluorescence lifetime also increases.
Description
Technical field
The invention belongs to fluorescence One-dimensional organic nano-material, particularly to high fluorescence one-dimensional organic semiconductor nanotube and
Its preparation method, and the application that this one-dimensional organic semiconductor nanotube is in terms of improving fluorescence quantum yield.
Background technology
The fluorescence One-dimensional organic nano-material prepared as construction unit using pi-conjugated organic molecule, owing to it is at optics
The potential application prospect of sensor, photonic propulsion and field of photoelectric devices, attracted all the time people pay close attention to widely and
Research.
When the organic nano material of design synthesis high-fluorescence quantum yield, two kinds of methods are generally utilized to avoid owing to having
The serious fluorescent quenching that the intermolecular strong π-π of machine acts on and causes.One is by MOLECULE DESIGN, such as, introduce steric hindrance bigger
Group or nonplanar MOLECULE DESIGN, weaken the tightness degree of pi-pi accumulation during self assembly of organic molecules.Wü
Rthner seminar constitutes the π-pi-conjugated of configuration distortion by introducing the substituent group of big steric hindrance to acid imide intramolecular
Construction unit, during molecular self-assembling, intermolecular form hydrogen bond thus obtains the monodimension nanometer material of high fluorescence.Phase
As, Pei Jian seminar once assembled the 1-dimention nano having obtained high fluorescence by the hydrogen bond action between Three-dimensional Rigidity molecule of the skeleton
Line.This method can effectively be avoided close pi-pi accumulation and obtain the organic nano material of high fluorescence, but accordingly can
Cause the weakening of photoelectric property of this kind of material.Second method be design synthesis plane configuration molecule as construction unit,
The organic nano material of high fluorescence is obtained by the accumulation mode of screw type, but the nano material of most of one-dimensional helical structure
The highest fluorescence quantum yield (not higher than 30%) can not be reached.In both approaches, the step of molecule synthesis is typically multiple
Miscellaneous and loaded down with trivial details, the cost of time and reagent is the highest.
Energy transfer process, such as exciton migration etc. can occur between the aggregation of ordered arrangement, and Ajayaghosh grinds
Study carefully group and the fluorescence intensity of material was once greatly improved by the monodimension nano stick of ordered arrangement, but self assembly is passed through in this research
The method of nanometer rods ordered arrangement is not had universality, makes all kinds of aggregations all energy in order by method simple to operation
Arrangement is still a difficult problem.Utilizing the interaction between aggregation to improve fluorescence quantum yield is also a neck the most leaved for development
Territory.
Summary of the invention
An object of the present invention one-dimensional organic semiconductor nanotube being to provide a kind of high fluorescence and preparation method thereof.
The two of the purpose of the present invention are to provide a kind of simple efficient fluorescence volume improving one-dimensional organic semiconductor nanotube
The method of sub-productivity, this method avoid the building-up process of complexity, also will not the intrinsic photoelectric property of expendable material.
The one-dimensional organic semiconductor nanotube of the high fluorescence of the present invention, is had asymmetric amphipathic substituent group by two ends
Imide derivative, is obtained by the π-π interaction self assembly between described acid imide.
In the present invention, described two ends have the imide derivative of asymmetric amphipathic substituent group and preferably have formula
(I) structure shown in:
In formula (I),
R1For C6-20Straight chained alkyl；
R2For R3The substituted phenyl of O-, R3For C3-10Branched alkyl.
Preferably, described R1For C8-18Straight chained alkyl.It is further preferred that R1For C10-16Straight chained alkyl.
Preferably, R3For C3-8Branched alkyl.
Preferably, described R3It is R4Or R5In one:
Preferably, described R3The position of substitution of O-is 3-position or 2-position (being 1 with the position that ethylidene is connected) of phenyl,
The preferably 3-position of phenyl.
In the present invention, the length of the one-dimensional organic semiconductor nanotube of described high fluorescence is about 5-20 micron, pipe external diameter
Being about 11-23 nanometer, wall thickness is 2.5-5 nanometer.Described nanotube has the homogeneous hollow tubular structure of Nano grade.
The two ends of the present invention have asymmetric amphipathic substituent group (R1For straight chain senior alkyl, R2Replace for branched alkoxy
Phenyl) imide derivative in, asymmetric end group substituent group can the most accurately adjust
π-π between acid imide interacts, thus obtains the one-dimensional organic semiconducting materials of special appearance (represented here as a wiener
Rice tubular structure).In the present invention, this homogeneous tubular structure can be with spontaneous orderly closely arranging along the direction being perpendicular to major axis
Row so that the Interaction enhanced between aggregation, can occur energy to shift, fluorescence quantum yield is significantly increased between pipe.
The preparation method of the one-dimensional organic semiconductor nanotube of the high fluorescence of the present invention is first to synthesize two ends and have not
Symmetrical amphipathic substituent group imide derivative as construction unit, then the good solvent in certain proportioning is molten with bad
In the mixed liquor of agent, being interacted by the π-π between acid imide, self assembly obtains described one-dimensional organic semiconductor nanometer
Pipe.
Specifically, described preparation method comprises the following steps:
(1) by acid anhydride and C6-20Straight chain alkyl amine reaction prepare the product of structure shown in formula (II):
In formula (II), R1For C6-20Straight chained alkyl；Preferably, described R1For C8-18Straight chained alkyl；It is further preferred that R1For
C10-16Straight chained alkyl.Wherein, described acid anhydride has structure shown in formula (III)；
(2) product of step (1) and the compound of structure shown in formula (IV) are reacted prepare described two ends have the most right
Claim amphipathic substituent group imide derivative；
R2-(CH2)2-NH2
(IV)
In formula (IV), R2The same formula of definition (I)；
(3) step (2) is obtained imide derivative be dissolved in good solvent, be subsequently adding poor solvent, quiet
Put, by described imide derivative, obtained containing described Gao Ying by the π-π interaction self assembly between acid imide
The suspension of the one-dimensional organic semiconductor nanotube of light.
In step (1), described acid anhydride is added described C after dissolving the organic solvent mixed dissolution of described acid anhydride6-20
Straight chain alkyl amine, react to obtain reactant liquor, in reactant liquor, then add stirring reaction after alcohol and concentrated hydrochloric acid, after having reacted,
Rinse to neutral with water, dry, obtain product.Described organic solvent is preferably imidazoles, methanol etc..Described acid anhydride and organic solvent
Weight ratio (g/g) is 1:80-1:200, preferably 1:100.Described mixed dissolution is carried out under heating, and preferably heating-up temperature is 100-
150 DEG C (more preferably 130 DEG C).Described acid anhydride and described C6-20The mol ratio (mol/mol) of straight chain alkyl amine be 1:0.5-1:
2, preferably 1:1.Described alcohol preferred alcohol.
In step (2), take the product obtained after step (1) is dried, be added thereto to organic solvent (such as imidazoles, methanol etc.)
And the compound of structure shown in formula (IV), react under temperature is 120-180 DEG C (preferably 140 DEG C), then to obtaining
Reactant liquor adds stirring reaction after the concentrated hydrochloric acid of 8～15 milliliters, after having reacted, obtains described imide derivative.
Wherein, the product of described step (1) is 1:80-1:200, preferably 1:100 with the weight ratio (g/g) of organic solvent.Described step
(1) product is 1:0.5-1:2, preferably 1:1 with the mol ratio (mol/mol) of the compound of structure shown in formula (IV).
In step (3), described good solvent is 1:10-1:20, preferably 1:15 with the volume ratio of poor solvent.Described is good molten
Agent is chloroform；Described poor solvent is ethanol or acetone.
The present invention also provides for the side of a kind of simple efficient fluorescence quantum yield improving one-dimensional organic semiconductor nanotube
Method, its be dispersed through in poor solvent by described one-dimensional organic semiconductor nanotube after carry out drop coating and form nanotube films,
By increasing the thickness of described film, the fluorescence quantum yield of described one-dimensional organic semiconductor nanotube can be greatly improved.
In said method, described poor solvent is selected from ethanol or acetone.
In said method, described one-dimensional organic semiconductor nanotube, in the nanotube films formed, nanotube is spontaneous
Assemble along the direction being perpendicular to pipe and form nanotube bundle not of uniform size.Along with the increase of film thickness, nanotube bundle increase and
Bundle diameters increases, and the fluorescence quantum yield of nanotube increases, and fluorescence lifetime increases.
Also energy can be occurred between the homogeneous tubular structure of the tightly packed laid out in parallel that the present invention designs synthesis to shift, from
And the photoluminescent property of material is greatly improved；Meanwhile, the molecules align of described nanotube does not change, and maintains original excellent
Good photoelectric property.
The invention has the beneficial effects as follows:
The one-dimensional organic semiconductor nanotube of the present invention has the homogeneous tubular structure of nanoscale, and can spontaneous be arranged in
Orderly nanotube bundle, by increasing the accumulation tightness degree of nanotube bundle, i.e. simple increasing is formed with nanotube bundle
The thickness of nanotube films, it is possible to improve the energy transfer between nanotube, thus the fluorescence volume of nano-tube material be greatly improved
Sub-productivity, maintains the original excellent photoelectric property of nanotube.
The core purpose of the present invention is to provide a kind of simple efficient fluorescence volume improving one-dimensional organic semiconductor nanotube
The method of sub-productivity.Being synthesized by design has asymmetric amphipathic for the two ends assembling one-dimensional organic semiconductor nanotube
The imide derivative monomer structure of substituent group, utilizes the difference of organic solvent dissolubility to carry out self assembly, thus obtains this
The one-dimensional organic semiconductor nanotube of the high fluorescence of invention.(length is about 5-20 micron to this one-dimensional organic semiconductor nanotube, pipe
External diameter is about 11-23 nanometer, wall thickness 2.5-5 nanometer) be dispersed through in poor solvent after, drop coating can make on different substrates and receive
Mitron film, by increase film thickness, can be greatly improved described one-dimensional organic semiconductor nanotube fluorescence quantum yield (from
21% improves to 54%).
Accompanying drawing explanation
Fig. 1. one end of the embodiment of the present invention 1 is 3-isopropoxy phenethyl, and the other end is that dodecyl chain is substituted
The nuclear magnetic data spectrogram of imide derivative monomer.
Fig. 2. one end of the embodiment of the present invention 1 is 3-isopropoxy phenethyl, and the other end is that dodecyl chain is substituted
The mass spectrometric data spectrogram of imide derivative monomer, relative molecular mass is 720.5.
Fig. 3. one end of the embodiment of the present invention 2 is 3-(2-ethylpropoxy) phenethyl, and the other end is that dodecyl chain takes
The nuclear magnetic data spectrogram of the imide derivative monomer in generation.
Fig. 4. one end of the embodiment of the present invention 2 is 3-(2-ethylpropoxy) phenethyl, and the other end is that dodecyl chain takes
The mass spectrometric data spectrogram of the imide derivative monomer in generation, relative molecular mass is 748.6.
Fig. 5. the one-dimensional organic semiconductor nanotube bundle of the embodiment of the present invention 1 and 2 and the TEM picture of single nanotube.Figure
5a, c are one-dimensional organic semiconductor nanotube bundle and the TEM picture of single nanotube of embodiment 1, and Fig. 5 b, d are embodiment 2
One-dimensional organic semiconductor nanotube bundle and the TEM picture of single nanotube.
Fig. 6. the TEM picture of the film that the one-dimensional organic semiconductor nanotube of the embodiment of the present invention 1 and 2 is thicker.Fig. 6 a is real
Executing the TEM picture of the thicker film of the one-dimensional organic semiconductor nanotube of example 1, Fig. 6 b is that the one-dimensional organic semiconductor of embodiment 2 is received
The TEM picture of the film that mitron is thicker.
Fig. 7. by Fourier's infrared light of the film of the different-thickness of the one-dimensional organic semiconductor nanotube of the embodiment of the present invention 1
Spectrum.
Fig. 8. the fluorescence quantum yield of the one-dimensional organic semiconductor nanotube films of the embodiment of the present invention 1 and 2 and sample thickness
The relation curve of degree.Solid line is fluorescence quantum yield and the sample film thickness of the one-dimensional organic semiconductor nanotube films of embodiment 1
Relation curve, dotted line is fluorescence quantum yield and the sample film thickness of the one-dimensional organic semiconductor nanotube films of embodiment 2
Relation curve.
Fig. 9. the fluorescence lifetime of the film of 3 kinds of different-thickness that the one-dimensional organic semiconductor nanotube of the embodiment of the present invention 1 drips.
Figure 10. by the fluorescent emission of the film of the different-thickness of the one-dimensional organic semiconductor nanotube of the embodiment of the present invention 1 and 2
Spectrum.Figure 10 a is the fluorescence spectrum of the one-dimensional organic semiconductor nanotube films of two kinds of thickness of embodiment 1, and Figure 10 b is embodiment
The fluorescence spectrum of the one-dimensional organic semiconductor nanotube films of two kinds of thickness of 2.
Figure 11. the side SEM picture of the one-dimensional organic semiconductor nanotube films of the embodiment of the present invention 1 and 2.Figure 11 a-e is
The side SEM picture of the one-dimensional organic semiconductor nanotube films of the embodiment of the present invention 1, Figure 11 f-j is the one of the embodiment of the present invention 2
The side SEM picture of dimension organic semiconductor nanotube films.
Detailed description of the invention
As it has been described above, the invention discloses the one-dimensional organic semiconductor nanotube of a kind of high fluorescence, (it is micro-that length is about 5-20
Rice, pipe external diameter is about 11-23 nanometer, and wall thickness is 2.5-5 nanometer), after described nanotube is dispersed through in ethanol or acetone, can drip
It is coated with and makes nanotube films on different substrates.There is the physics shape of the homogeneous tubular structure of Nano grade due to described nanotube
Looks, described one-dimensional organic semiconductor nanotube can be gathered into nanotube bundle not of uniform size, as it is shown in figure 5, nanotube is along hanging down
Straight in the direction laid out in parallel of major axis, nanotube bundle diameters 50nm-500nm.
When the thickness of the film that the one-dimensional organic semiconductor nanotube of the high fluorescence of the present invention is formed increases, nanotube compact reactor
Quantity and the diameter of the long-pending nanotube bundle formed increase (as shown in Figure 6) the most accordingly.By testing the nanotube films of different-thickness
FTIR spectrum (as shown in Figure 7), find along with nanotube films thickness increase, 1163cm-1On the alkoxyl at place
CH-O vibration peak is relative to 2923cm-1CH on place's long alkyl chain2Vibration peak constantly reduces, and illustrates that being exposed to outer alkoxyl is received
Interaction between mitron reduces vibration, illustrates that the accumulation degree between nanotube is more and more tightr.
After being dispersed through in ethanol or acetone by the one-dimensional organic semiconductor nanotube of the present invention, drop coating is made in substrate
Nanotube films, along with the increase (from 50nm to 500nm) of described film thickness, its fluorescence quantum yield increases to 54% from 21%
(as shown in Figure 8).
Found by the fluorescence lifetime (as shown in Figure 9) measuring the nanotube films of the present invention, along with the increase of film thickness, its
Fluorescence lifetime increases accordingly, illustrates that the energy transfer between nanotube is corresponding and strengthens.And the fluorescence light of the nanotube films of different-thickness
Spectrum (as shown in Figure 10) only there occurs the change of fluorescence intensity, illustrates that the molecules align in nanotube does not change, thus
Maintain the photoelectric property that this nano-tube material is intrinsic.
Below by way of detailed description of the invention, the present invention is described in further detail, but this should be interpreted as the present invention
Scope be only limitted to Examples below.In the case of without departing from said method thought of the present invention, according to ordinary skill
Various replacements that knowledge and customary means are made or change, should be included in the scope of the present invention.
Embodiment 1
It is 3-isopropoxy phenethyl that preparation has one end of following molecular formula, and the other end is that dodecyl chain is substituted
Imide derivative monomer.
(1)-3,4,9,10-the tetracarboxylic dianhydride of 100 milligrams and the imidazoles of 10 grams are mixed and heated to 130 DEG C of dissolvings
After be injected into and 40 milligrams of lauryl amines carry out reaction obtain reactant liquor, then add in reactant liquor 15 milliliters ethanol and
It is stirred overnight after the concentrated hydrochloric acid of 15 milliliters；Taking out product, it is neutral for rinsing to pH with water, dries；
(2) take the product 100 milligrams obtained after step (1) is dried, be added thereto to imidazoles and the 3-of 300 microlitres of 10 grams
Isopropoxy phenethylamine, reacts at temperature is 140 DEG C, then adds 8～15 milliliters dense in the reactant liquor obtained
It is stirred overnight after hydrochloric acid, takes out product, obtain imide derivative；
(3) add poor solvent after being dissolved in good solvent by the imide derivative that step (2) obtains, stand, by
Imide derivative, obtains containing many one-dimensional organic by the π-π interaction self assembly between described acid imide
The suspension of semiconducting nanotubes.Wherein good solvent is 1:15 with the volume ratio of poor solvent.Described good solvent is chloroform；Institute
The poor solvent stated is ethanol or acetone.
It is dispersed through making the suspension of about 14 μ g/ml in poor solvent by above-mentioned one-dimensional organic semiconductor nanotube
After, on polytetrafluoroethylene film, drip the suspension of 50,100,200,300,500,600 μ L volumes respectively, after draining solvent
The nanotube films formed carries out the measurement of fluorescence quantum yield, and fluorescence quantum yield increases to 54% from 21%.Shot by SEM
Measure the thickness (as shown in Figure 11 a-e) of film, the relation curve of film thickness and its fluorescence quantum yield can be obtained.
The assay method of fluorescence quantum yield: by sample drop on polytetrafluoroethylene film, measuring instrument is
Hamamatsu C11247 fluorescence quantum yield spectrogrph.Test choose multi-wavelength scanning pattern, 450nm, 480nm,
Measuring fluorescent quantum yield under 510nm, 540nm wavelength, the sample film of each thickness drips 3 diaphragms and does parallel testing, takes
Average.
Embodiment 2
It is 3-(2-ethylpropoxy) phenethyl that preparation has one end of following molecular formula, and the other end is that dodecyl chain takes
The imide derivative monomer in generation.
(1)-3,4,9,10-the tetracarboxylic dianhydride of 100 milligrams and the imidazoles of 10 grams are mixed and heated to 130 DEG C of dissolvings
After be injected into and 40 milligrams of lauryl amines carry out reaction obtain reactant liquor, then add in reactant liquor 15 milliliters ethanol and
It is stirred overnight after the concentrated hydrochloric acid of 15 milliliters；Taking out product, it is neutral for rinsing to pH with water, dries；
(2) take the product 100 milligrams obtained after step (1) is dried, be added thereto to imidazoles and the 3-of 300 microlitres of 10 grams
Isoamoxy phenethylamine, reacts at temperature is 140 DEG C, then adds 8～15 milliliters dense in the reactant liquor obtained
It is stirred overnight after hydrochloric acid, takes out product, obtain imide derivative；
(3) add poor solvent after being dissolved in good solvent by the imide derivative that step (2) obtains, stand, by
Imide derivative, obtains containing many one-dimensional organic by the π-π interaction self assembly between described acid imide
The suspension of semiconducting nanotubes.Wherein good solvent is 1:15 with the volume ratio of poor solvent.Described good solvent is chloroform；Institute
The poor solvent stated is ethanol.
It is dispersed through making the suspension of about 14 μ g/ml in poor solvent by above-mentioned one-dimensional organic semiconductor nanotube
After, on polytetrafluoroethylene film, drip the suspension of 50,100,200,300,500,600 μ L volumes respectively, after draining solvent
The nanotube films formed carries out the measurement of fluorescence quantum yield, and fluorescence quantum yield increases to 55% from 30%.Shot by SEM
The thickness (as shown in Figure 11 f-j) of film, can obtain the relation curve of film thickness and its fluorescence quantum yield.
The assay method of fluorescence quantum yield: by sample drop on polytetrafluoroethylene film, measuring instrument is
Hamamatsu C11247 fluorescence quantum yield spectrogrph.Test choose multi-wavelength scanning pattern, 450nm, 480nm,
Measuring fluorescent quantum yield under 510nm, 540nm wavelength, the sample film of each thickness drips 3 diaphragms and does parallel testing, takes
Average.
Claims (11)
1. the method for the simple efficient fluorescence quantum yield improving one-dimensional organic semiconductor nanotube, it is characterised in that
Described method includes: carries out drop coating after being dispersed through in poor solvent by one-dimensional organic semiconductor nanotube and forms nanotube films,
By increasing the thickness of described film, improve the fluorescence quantum yield of described one-dimensional organic semiconductor nanotube；
Wherein, described one-dimensional organic semiconductor nanotube is to be had the acid imide of asymmetric amphipathic substituent group by two ends to spread out
Biology, is obtained by the π-π interaction self assembly between described acid imide.
Method the most according to claim 1, it is characterised in that described two ends have asymmetric amphipathic substituent group
Imide derivative has a structure shown in formula (I):
In formula (I),
R1For C6-20Straight chained alkyl；
R2For R3The substituted phenyl of O-, R3For C3-10Branched alkyl.
Method the most according to claim 2, it is characterised in that described R1For C8-18Straight chained alkyl.
Method the most according to claim 3, it is characterised in that R1For C10-16Straight chained alkyl.
Method the most according to claim 2, it is characterised in that R3For C3-8Branched alkyl.
Method the most according to claim 5, it is characterised in that described R3It is R4Or R5In one:
Method the most according to claim 2, it is characterised in that described R3The position of substitution of O-is 3-position or the 2-position of phenyl,
It it is 1 with the position that ethylidene is connected.
Method the most according to claim 7, it is characterised in that described R3The position of substitution of O-is the 3-position of phenyl.
Method the most according to claim 1, it is characterised in that a length of 5-of described one-dimensional organic semiconductor nanotube
20 microns, pipe external diameter is 11-23 nanometer, and wall thickness is 2.5-5 nanometer；Described nanotube has the homogeneous hollow pipe of Nano grade
Shape structure.
Method the most according to claim 1, it is characterised in that described poor solvent is selected from ethanol or acetone.
11. methods according to claim 10, it is characterised in that formed by described one-dimensional organic semiconductor nanotube
In nanotube films, spontaneous the assembling along the direction being perpendicular to pipe of nanotube forms nanotube bundle not of uniform size；Along with film thickness
Increase, nanotube bundle increases and bundle diameters increases, and the fluorescence quantum yield of nanotube increases, and fluorescence lifetime increases.
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