CN101942210A - 4-amido-1,8-naphthalimide derivative fluorescent dichroic dye and application thereof - Google Patents
4-amido-1,8-naphthalimide derivative fluorescent dichroic dye and application thereof Download PDFInfo
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- CN101942210A CN101942210A CN201010289096XA CN201010289096A CN101942210A CN 101942210 A CN101942210 A CN 101942210A CN 201010289096X A CN201010289096X A CN 201010289096XA CN 201010289096 A CN201010289096 A CN 201010289096A CN 101942210 A CN101942210 A CN 101942210A
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Abstract
The invention provides a 4-amido-1,8-naphthalimide derivative fluorescent dichroic dye and application thereof, and belongs to the field of display materials. The 4-amido-1,8-naphthalimide derivative fluorescent dichroic dye is prepared by introducing substituted amino into naphthalimide serving as a matrix and modifying the matrix, and has the advantages of fluorescent dichroism, novel structure, readily available raw materials and simple synthesis method. Tests prove that the dye has bright yellow green fluorescence, maximum transmission wavelength of 497nm and fluorescence quantum yield of between 0.67 and 0.74, shows good dichroism in liquid crystal MLC6237-01 epsilon, has an absorption order parameter of between -0.11 and -0.12, dichroic ratio of between 1.3 and 1.5, fluorescent order parameter of between -0.38 and -0.40, and fluorescent dichroic ratio of between 6.3 and 7.1.
Description
Technical field
The present invention relates to a class 4-amino-1, and two tropism's dyestuff and the application thereof of 8-naphthalimide derivatives fluorescent belong to the display material field.
Background technology
[0002] why " guest-master " type liquid-crystal display can become the indicating meter that a class has application prospect, exactly because it shows not only that information is bright in luster, brightness is high, good contrast, visual angle are wide, and when assembling, only need use a slice polaroid even not use polaroid, this has just improved the light utilization efficiency of backlight greatly.Especially in recent years the development of fluorescence dichroism liquid crystalline dyes, be applied in " guest-master " demonstration, the bright-coloured coloured light of emissive display and the characteristics of high brightness and liquid-crystal display can be combined, can become the lower portable electronic products indicating meter of a kind of energy consumption.
" guest-master " liquid-crystal display is divided into the positivity demonstration and negativity shows, wherein positivity shows the custom of watching that meets people.And in realizing the method that positivity shows, use positivity liquid crystal and negativity dichroic dye the most reasonable.The fluorescence dichroism liquid crystalline dyes of bibliographical information all belongs to positive dichroic dye at present, has limited its application development greatly.Therefore, seek a kind of negative fluorescence dichroism liquid crystalline dyes of excellent property, have important Research Significance and using value.
Summary of the invention
The objective of the invention is to introduce amino group in the 4-position of naphthalimide, utilize amino strong electronic effect and the amide group structure on the naphthalimide with strong electron-withdrawing power of giving to form strong push-and-pull electron system, obtain yellow-green colour colour system fluorescence dye, further modify amino expectation simultaneously and improve solubleness and the dichroism of molecule in liquid crystal.
4-amino-1 of the present invention, the 8-naphthoyl imide compounds is to introduce the 4-hydroxy piperidine group with strong electron donation in the 4-position of naphthalimide, secondly, passes through esterification, further modify molecular structure of dye, a series of naphthalimide analog derivatives have been synthesized in design.
The technical scheme that is adopted that the present invention solves the problems of the technologies described above is: a class 4-amino-1, and 8-naphthalimide derivatives fluorescent two tropism's liquid crystalline dyes, its chemical molecular general structure is as follows:
In the general formula I:
R
1Be C
1-C
12Straight chained alkyl, cycloalkyl, aromatic base or substituted aromatic base; Or the list that contains F replaces or polysubstituted C
1-C
12Straight chained alkyl, alkoxyl group, aromatic base;
R
2Be H, F, CN or CF
3
R
3Be H, F, CN or CF
3
R
4Be H, F, CN, C
1-C
12Straight chained alkyl, alkoxyl group or contain the single of F and replace or polysubstituted C
1-C
12Straight chained alkyl, alkoxyl group;
R
5Be H, F, CN or CF
3
R
6Be H, F, CN or CF
3
Concrete synthetic route is as follows:
Promptly with 4-bromo-1,8-naphthalene acid anhydride (A) is a starting raw material, at first with replacement primary amine generation amidate action, generate 4-bromo-N-substituting group-1,8-naphthalimide (B), then generate 4-(p-hydroxy piperidine base with the reaction of 4-hydroxy piperidine)-N-substituting group base-1,8-naphthalimide (C), last and various substituted benzoyl chloride reactions generate target product (I).
Is 0.5%(w/w with dyestuff I according to weight concentration) ratio be incorporated in the liquid crystal, at room temperature mix, the liquid crystal cell of then this mixture being packed into is sealed and is irritated brilliant mouthful.Absorbance A on difference test dye and the liquid crystal cell alignment films parallel direction
‖With the absorbance A on the vertical direction
⊥, the fluorescence intensity F on the parallel direction
‖With the fluorescence intensity F on the vertical direction
⊥And calculate dyestuff according to following formula (1), (2), (3), (4) and in liquid crystal, be absorbed with order parameter S
A, dichroic compares D
AWith fluorescence order parameter S
F, dichroic compares D
F
（1）
（2）
Beneficial effect of the present invention: this 4-amino-1,8-naphthalimide derivatives fluorescent two tropism's dyestuffs are parent with the naphthalimide, obtain by introducing substituted-amino in the 4-position and being modified, has negative fluorescence dichroism, and its novel structure, raw material is easy to get, and synthetic method is simple.Can get after tested, this series dyes has bright-coloured yellow-green colour colour system fluorescence, maximum emission wavelength is 497nm, fluorescence quantum yield is 0.67-0.74, show dichroism preferably in liquid crystal MLC6237-01 ε, being absorbed with order parameter is-0.11 ~-0.12, and the dichroic ratio is 1.3 ~ 1.5, the fluorescence order parameter is-0.38 ~-0.40, and the fluorescence dichroic is than being 6.3-7.1.
Embodiment
Embodiment 1
4-(4 '-benzoic ether piperidyl)-N-n-propyl-1,8 naphthalimide (I1) synthetic
(1) in the 25mL two-mouth bottle, add 0.544g(2mmol) 4-bromo-1,8-naphthalene acid anhydride, the 15mL dehydrated alcohol adds the 2.4mmol Tri N-Propyl Amine under the stirring at room, be heated to backflow, TLC point plate tracks to and reacts completely, and stopped reaction is cooled to room temperature, separate out a large amount of solids, suction filtration, washing, dry, obtain product, be directly used in next step reaction, productive rate: 90%.
(2) in the 25mL two-mouth bottle, add 1.5mmol 4-bromo-N-n-propyl-1, the 8-naphthalimide, 0.182g(1.8mmol) the 4-hydroxy piperidine, 10mL ethylene glycol monomethyl ether, magnetic agitation, heat temperature raising is to refluxing, and TLC point plate is followed the tracks of reaction to terminal, stopped reaction, cool to room temperature is poured in the 50mL water dichloromethane extraction, the organic phase anhydrous magnesium sulfate drying, rotation is steamed and is removed organic solvent then, obtains thick product, productive rate: 87%.
(3) in the 25mL two-mouth bottle, add 1mmol 4-(p-hydroxy piperidine base)-N-n-propyl-1,8-naphthalimide, 8mL anhydrous pyridine; 1.5mmol Benzoyl chloride, magnetic agitation vacuumizes, nitrogen protection; heat temperature raising is to refluxing, and TLC point plate tracks to and reacts completely stopped reaction.Be cooled to room temperature, pour in the 50mL water, dichloromethane extraction, the organic phase anhydrous magnesium sulfate drying filters, and revolves to boil off to desolventize, and residue is through column chromatography for separation, and developping agent is a methylene dichloride.Obtain yellow solid I1, productive rate: 47%, fusing point: 152.3-153.2 ℃.
1H-NMR?(400MHz，CDCl
3)，δ
H（ppm）：8.60?(d，J=7.2Hz，1H)，?8.53?(d，J=8.0Hz，1H)，8.42?(d,?J=8.4Hz，1H)，8.10?(d，J=7.2Hz，2H)，?7.72?(t，J
1=7.2Hz，J
2=8.4Hz，1H)，7.60?(dd，J
1=6.8Hz，J
2=7.2Hz，1H)，7.48?(dd，J
1=J
2=7.6Hz，2H)，7.27?(d，J=9.2Hz，1H)，5.36?(m，1H)，4.14?(t，J
1=J
2=7.6Hz，2H)，3.53?(m,?2H)，3.28?(m,?2H)，2.34?(m，2H)，2.20?(m，2H)，1.75?(m，2H)，1.01?(t，J
1=J
2=7.2Hz，3H)。
HR-MS (EI): C
27H
26N
2O
4(M
+), calculated value: 442.1893, measured value: 442.1903.
Embodiment 2
4-(4 '-benzoic ether piperidyl)-N-normal-butyl-1,8 naphthalimide (I2) synthetic
Except that replacing with n-Butyl Amine 99 the Tri N-Propyl Amine, other synthetic and methods of purification obtain target product I2, productive rate with embodiment 1: 49%, and fusing point: 138.9-140.9 ℃.
1H-NMR?(400MHz，CDCl
3)，δ
H（ppm）：8.60?(d，J=6.8Hz，1H)，8.53?(d，J=8.0Hz，1H)，8.42?(d，J=8.4Hz，1H)，8.10?(d，J=7.2Hz，2H)，7.72?(t，J
1=8.0Hz，J
2=7.6Hz，1H)，7.60?(dd，J
1=7.6Hz，J
2=7.2Hz，1H)，7.48?(dd，J
1=8.0Hz，J
2=7.2Hz，2H)，7.27?(d，J=9.6Hz，1H)，5.36?(m，1H)，4.17?(t，J
1=8.0Hz，J
2=7.2Hz，2H)，3.53?(m，2H)，3.28?(m，2H)，2.34?(m，2H)，2.20?(m，2H)，1.71?(m，2H)，1.45?(m，2H)，0.97?(t，J
1=J
2=7.2Hz，3H)。
HR-MS (EI): C
28H
28N
2O
4(M
+), calculated value: 456.2049, measured value: 456.2055.
Embodiment 3
4-(4 '-benzoic ether piperidyl)-N-n-hexyl-1,8 naphthalimide (I3) synthetic
Except that replacing with normal hexyl Amine the Tri N-Propyl Amine, other synthetic and methods of purification obtain target product I3, productive rate with embodiment 1: 49%, and fusing point: 155.7-157.0 ℃.
1H-NMR?(400MHz，CDCl
3)，δ
H（ppm）：8.60?(d，J=7.2Hz，1H)，8.53?(d，J=8.0Hz，1H)，8.42?(d，J=8.4Hz，1H)，8.10?(d，J=7.6Hz，2H)，7.72?(t，J
1=7.2Hz，J
2=8.0Hz，1H)，7.60?(dd，J
1=8.0Hz，J
2=7.6Hz，1H)，7.48?(dd，J
1=J
2=7.6Hz，2H)，7.27?(d，J=8.0Hz，1H)，5.36?(m，1H)，4.16?(t，J
1=J
2=7.6Hz，2H)，3.53?(m，2H)，3.28?(m，2H)，2.33?(m，2H)，2.20?(m，2H)，1.72?(m，2H)，1.32?(m，6H)，0.89?(t，J
1=J
2=6.8Hz，3H)。
HR-MS (EI): C
30H
32N
2O
4(M
+), calculated value: 484.2362, measured value: 484.236.
Embodiment 4
4-(4 '-benzoic ether piperidyl)-and the N-n-octylcyclam, 8 naphthalimides (I4) synthetic
Except that replacing with n-octyl amine the Tri N-Propyl Amine, other synthetic and methods of purification obtain target product I4, productive rate with embodiment 1: 42%, and fusing point: 126.9-127.9 ℃.
1H-NMR?(400MHz，CDCl
3)，δ
H（ppm）：8.60?(d，J=7.2Hz，1H)，8.53?(d，J=8.4Hz，1H)，8.45?(d，J=8.4Hz，1H)，8.10?(d，J=7.6Hz，2H)，7.73?(t，J
1=8.0Hz，J
2=8.4Hz，1H)，7.60?(dd，J
1=7.2Hz，J
2=7.6Hz，1H)，7.48?(dd，J
1=7.6Hz，J
2=8.0Hz，2H)，7.27?(d，J=8.0Hz，1H)，5.36?(m，1H),?4.16?(t，J
1=8.0Hz，J
2=7.2Hz，2H)，3.55?(m，2H)，3.44?(m，2H)，2.35?(m，2H)，2.21(m，2H)，1.72?(m，2H)，1.33?(m，10H)，0.87?(t，J
1=J
2=6.8Hz，3H)。
HR-MS (EI): C
32H
36N
2O
4(M
+), calculated value: 512.2675, measured value: 512.2683.
Embodiment 5
4-(4 '-benzoic ether piperidyl)-N-positive dodecyl-1,8 naphthalimide (I5) synthetic
Except that replacing the Tri N-Propyl Amine with positive amino dodecane, other synthetic and methods of purification obtain target product I5, productive rate with embodiment 1: 43%, and fusing point: 89.6-90.8 ℃.
1H-NMR?(400MHz，CDCl
3)，δ
H（ppm）：8.60?(d，J=7.6Hz，1H)，8.53?(d，J=8.0Hz，1H)，8.45?(d，J=8.4Hz，1H)，8.10?(d，J=7.2Hz，2H)，7.73?(t，J
1=8.4Hz，J
2=7.6Hz，1H)，7.60?(dd，J
1=7.2Hz，J
2=7.6Hz，1H)，7.48?(dd，J
1=J
2=7.6Hz，2H)，7.29?(d，J=7.2Hz，1H)，5.36?(m，1H)，4.16?(t，J
1=7.2Hz，J
2=7.6Hz，2H)，3.55?(m，2H)，3.30?(m，2H)，2.36?(m，2H)，2.21?(m，2H)，1.71?(m，2H)，1.30?(m，18H)，0.87?(t，J
1=J
2=7.2Hz，3H)。
HR-MS (EI): C
36H
44N
2O
4(M
+), calculated value: 568.3301, measured value: 568.3311.
Embodiment 6
The spectral quality test of dyestuff in methylene dichloride:
Test result to Compound I 1-5 is as follows:
Absorption and the fluorescence data of table 1 dyestuff I1-5 in methylene dichloride
| Compound | λ max/nm | δ/nm | λ em/nm | δ F/nm | ㏒ξ | Ф FL | Stokes shift/nm |
| I1 | 398 | 71 | 506 | 70 | 4.04 | 0.67 | 108 |
| I2 | 397 | 69 | 507 | 70 | 3.94 | 0.72 | 110 |
| I3 | 400 | 65 | 506 | 70 | 3.92 | 0.73 | 106 |
| I4 | 400 | 67 | 507 | 70 | 3.94 | 0.74 | 107 |
| I5 | 400 | 65 | 507 | 70 | 3.97 | 0.70 | 107 |
Embodiment 7
The polarisation spectrum property detection of dyestuff in liquid crystal:
Test is the commercially available prod with main body liquid crystal MLC 6237-01 ε.Test used liquid crystal cell and be made of two sheet glass substrates, the surface scribbles the polyimide film that makes dyestuff and liquid crystal main body be parallel to the glass substrate orientation, and thickness of liquid crystal box is 7 μ m.
Each dyestuff of I series is incorporated in the used liquid crystal of test according to 0.5% ratio (mass ratio), mixes under the room temperature, and then the liquid crystal material that contains the N dyestuff that this prepares is injected in the liquid crystal cell, seal and irritate brilliant mouthful., measure ultraviolet-visible polarisation spectrum (ultra-violet absorption spectrum with liquid crystal material is a benchmark) and fluorescent emission polarisation spectrum.
Be absorbed with order parameter and dichroic ratio, fluorescence order parameter and dichroic ratio according to what test spectral and formula (1), (2), (3) and (4) calculated dyestuff respectively.
Dyestuff I1-5 polarisation spectrum test result is as follows:
Absorption and the fluorescence data of table 2 dyestuff I1-5 in liquid crystal MLC 6237-01 ε
| Compound | λ max/nm | λ em/nm | S A | D A | S F | D F |
| I1 | 406 | 495 | -0.11 | 1.3 | -0.39 | 6.4 |
| I2 | 407 | 497 | -0.12 | 1.4 | -0.39 | 6.3 |
| I3 | 407 | 495 | -0.11 | 1.4 | -0.38 | 7.1 |
| I4 | 410 | 495 | -0.12 | 1.5 | -0.39 | 6.5 |
| I5 | 406 | 497 | -0.11 | 1.4 | -0.40 | 6.8 |
Claims (2)
1. a class 4-amino-1,8-naphthalimide derivatives fluorescent two tropism's liquid crystalline dyes is characterized in that: this dyestuff has following chemical molecular general structure:
In the general formula I:
R
1Be C
1-C
12Straight chained alkyl, cycloalkyl, aromatic base or substituted aromatic base; Or the list that contains F replaces or polysubstituted C
1-C
12Straight chained alkyl, alkoxyl group, aromatic base;
R
2Be H, F, CN or CF
3
R
3Be H, F, CN or CF
3
R
4Be H, F, CN, C
1-C
12Straight chained alkyl, alkoxyl group or contain the single of F and replace or polysubstituted C
1-C
12Straight chained alkyl, alkoxyl group;
R
5Be H, F, CN or CF
3
R
6Be H, F, CN or CF
3
2. according to the described class 4-amino-1 of claim 1, the application of 8-naphthalimide derivatives fluorescent two tropism's liquid crystalline dyes, it is characterized in that: is that 0.5% ratio is incorporated in the liquid crystal with dyestuff I according to weight concentration, at room temperature mix, the liquid crystal cell of then this mixture being packed into is sealed and is irritated brilliant mouthful; Absorbance A on difference test dye and the liquid crystal cell alignment films parallel direction
‖With the absorbance A on the vertical direction
⊥, the fluorescence intensity F on the parallel direction
‖With the fluorescence intensity F on the vertical direction
⊥And calculate dyestuff according to following formula (1), (2), (3), (4) and in liquid crystal, be absorbed with order parameter S
A, dichroic compares D
AWith fluorescence order parameter S
F, dichroic compares D
F:
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757662A (en) * | 2012-07-03 | 2012-10-31 | 大连理工大学 | Acylhydrazine containing 1,8-naphthalimide fluorescent dichroic dyes, as well as preparation method and application thereof |
| CN104194398A (en) * | 2014-07-28 | 2014-12-10 | 大连理工大学 | Fluorescent dichroic dyes containing 4-(p-hydroxy-piperidyl)-1,8-naphthalene dicarbonitrile as well as preparation method and applications thereof |
| CN109180639A (en) * | 2018-09-05 | 2019-01-11 | 大连理工大学 | The naphthalimide derivative that one kind replaces, preparation method and application |
| CN109336814A (en) * | 2018-09-05 | 2019-02-15 | 大连理工大学 | The naphthalimide derivative that one kind replaces containing 4- (alkyl bicyclic hexyl), preparation method and application |
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| CN1635047A (en) * | 2004-12-08 | 2005-07-06 | 中国科学院长春应用化学研究所 | Blue color electroluminescent macromolecular material and method for making same |
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2010
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| CN1635047A (en) * | 2004-12-08 | 2005-07-06 | 中国科学院长春应用化学研究所 | Blue color electroluminescent macromolecular material and method for making same |
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| Title |
|---|
| GHASEM REZANEJADE BARDAJEE ET AL.: "The synthesis and spectroscopic properties of novel,functional flurescent naphthalimide dyes", 《DYES AND PIGMENTS》, vol. 79, 25 January 2008 (2008-01-25), pages 24 - 32 * |
| WALDEMAR ADAM ET AL.: "Synthesis and photooxygenation of 2,3,6-Trimethylfuro[2,3-b][1]naphtho[4a,7a-e,f]pyrida-5,7-dione, A potential chemiluminescent probe for singlet oxygen", 《TETRAHEDRON》, vol. 49, no. 2, 8 January 1993 (1993-01-08), pages 417 - 422 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757662A (en) * | 2012-07-03 | 2012-10-31 | 大连理工大学 | Acylhydrazine containing 1,8-naphthalimide fluorescent dichroic dyes, as well as preparation method and application thereof |
| CN102757662B (en) * | 2012-07-03 | 2013-11-06 | 大连理工大学 | Acylhydrazine containing 1,8-naphthalimide fluorescent dichroic dyes, as well as preparation method and application thereof |
| CN104194398A (en) * | 2014-07-28 | 2014-12-10 | 大连理工大学 | Fluorescent dichroic dyes containing 4-(p-hydroxy-piperidyl)-1,8-naphthalene dicarbonitrile as well as preparation method and applications thereof |
| CN109180639A (en) * | 2018-09-05 | 2019-01-11 | 大连理工大学 | The naphthalimide derivative that one kind replaces, preparation method and application |
| CN109336814A (en) * | 2018-09-05 | 2019-02-15 | 大连理工大学 | The naphthalimide derivative that one kind replaces containing 4- (alkyl bicyclic hexyl), preparation method and application |
| CN109180639B (en) * | 2018-09-05 | 2020-06-02 | 大连理工大学 | Substituted naphthalimide derivative, preparation method and application thereof |
| CN109336814B (en) * | 2018-09-05 | 2020-08-14 | 大连理工大学 | 4- (alkyl dicyclohexyl) -substituted naphthalimide derivative, and preparation method and application thereof |
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| CN101942210B (en) | 2013-05-08 |
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