CN101942210B - 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 PDF

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CN101942210B
CN101942210B CN 201010289096 CN201010289096A CN101942210B CN 101942210 B CN101942210 B CN 101942210B CN 201010289096 CN201010289096 CN 201010289096 CN 201010289096 A CN201010289096 A CN 201010289096A CN 101942210 B CN101942210 B CN 101942210B
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liquid crystal
naphthalimide
fluorescent
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dyestuff
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CN101942210A (en
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李晓莲
王兵
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Dalian University of Technology
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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

One class 4-amino-1, two tropism's dyestuff and the application thereof of 8-naphthalimide derivatives fluorescent
Technical field
It is amino-1 that the present invention relates to a class 4-, 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 only need to use a slice polaroid even not use polaroid when assembling, 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 greatly limited its application development.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 at the 4-of naphthalimide position introducing amino group, utilize and amino strong to form strong push and pull component to electronic effect and amide group structure on the naphthalimide with strong electron-withdrawing power, obtain yellow-green colour colour system fluorescence dye, further modify simultaneously amino expectation and improve solubleness and the dichroism of molecule in liquid crystal.
4-of the present invention amino-1, 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 present invention solves the problems of the technologies described above the technical scheme that adopts: amino-1, the 8-naphthalimide of class 4-derivatives fluorescent two tropism's liquid crystalline dyes, and its chemical molecular general structure is as follows:
Figure 201010289096X100002DEST_PATH_IMAGE001
In 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:
Figure 596646DEST_PATH_IMAGE002
Namely with 4-bromo-1,8-naphthalene acid anhydride (A) is 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).
Be 0.5%(w/w with dyestuff I according to weight concentration) ratio be incorporated in liquid crystal, at room temperature mix, the liquid crystal cell of then this mixture being packed into seals the irrigation crystal mouth.Absorbance A on difference test dye and liquid crystal cell alignment films parallel direction ‖With the absorbance A on vertical direction ⊥, the fluorescence intensity F on parallel direction ‖With the fluorescence intensity F on vertical direction ⊥And calculate dyestuff according to following formula (1), (2), (3), (4) be absorbed with order parameter S in liquid crystal A, dichroic compares D AWith fluorescence order parameter S F, dichroic compares D F
Figure 201010289096X100002DEST_PATH_IMAGE003
（1）
Figure 327841DEST_PATH_IMAGE004
（2）
Figure 201010289096X100002DEST_PATH_IMAGE005
（3）
（4）
Beneficial effect of the present invention: this 4-amino-1,8-naphthalimide derivatives fluorescent two tropism's dyestuffs obtain by also being modified at 4-position introducing substituted-amino take naphthalimide as parent, 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) synthesizing of-N-n-propyl-1,8 naphthalimide (I1)
(1) in the 25mL two-mouth bottle, add 0.544g(2mmol) 4-bromo-1,8-naphthalene acid anhydride, add the 2.4mmol Tri N-Propyl Amine under 15mL dehydrated alcohol, stirring at room, be heated to reflux, 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%.
Figure DEST_PATH_IMAGE007
(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, be heated to backflow, TLC point plate is followed the tracks of reaction to terminal, stopped reaction, cool to room temperature is poured in 50mL water dichloromethane extraction, the organic phase anhydrous magnesium sulfate drying, then rotation is steamed except organic solvent, obtains thick product, productive rate: 87%.
Figure 731327DEST_PATH_IMAGE008
(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; be heated to backflow, TLC point plate tracks to and reacts completely, stopped reaction.Be cooled to room temperature, pour in 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 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.
Figure DEST_PATH_IMAGE009
Embodiment 2
4-(4 '-benzoic ether piperidyl) synthesizing of-N-normal-butyl-1,8 naphthalimide (I2)
Except replacing Tri N-Propyl Amine with n-Butyl Amine 99, other synthesizing progress methods 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) synthesizing of-N-n-hexyl-1,8 naphthalimide (I3)
Except replacing Tri N-Propyl Amine with normal hexyl Amine, other synthesizing progress methods 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)-N-n-octylcyclam, 8 naphthalimides (I4) synthetic
Except replacing Tri N-Propyl Amine with n-octyl amine, other synthesizing progress methods 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) synthesizing of-N-positive dodecyl-1,8 naphthalimide (I5)
Except replacing Tri N-Propyl Amine with n-dodecylamine, other synthesizing progress methods 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:
The Absorption and 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 liquid crystal cell used 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 test liquid crystal used according to 0.5% ratio (mass ratio), mixes under room temperature, and then the liquid crystal material that contains the N dyestuff that this prepares is injected in liquid crystal cell, seal the irrigation crystal mouth., measure ultraviolet-visible polarized absorption spectra (take the ultra-violet absorption spectrum of liquid crystal material as benchmark) and fluorescent emission polarized absorption spectra.
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 respectively dyestuff.
Dyestuff I1-5 polarisation spectrum test result is as follows:
The Absorption and 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-is amino-1, and 8-naphthalimide derivatives fluorescent two tropism's liquid crystalline dyes is characterized in that: this dyestuff has following chemical molecular general structure:
Figure FDA0000272280721
In general formula I:
R 1Be C 1-C 12Straight chained alkyl;
R 2Be H;
R 3Be H;
R 4Be H;
R 5Be H;
R 6Be H.
2. according to a class 4-amino-1 claimed in claim 1, the application of 8-naphthalimide derivatives fluorescent two tropism's liquid crystalline dyes, it is characterized in that: be that 0.5% ratio is incorporated in liquid crystal with dyestuff I according to weight concentration, at room temperature mix, then the liquid crystal cell of this mixture being packed into seals the irrigation crystal mouth; Absorbance A on difference test dye and liquid crystal cell alignment films parallel direction ‖With the absorbance A on vertical direction ⊥, the fluorescence intensity F on parallel direction ‖With the fluorescence intensity F on vertical direction ⊥And calculate dyestuff according to following formula (1), (2), (3), (4) be absorbed with order parameter S in liquid crystal A, dichroic compares D AWith fluorescence order parameter S F, dichroic compares D F:
S A = A / / - A ⊥ A / / + 2 A ⊥ - - - ( 1 ) ;
D A = A / / A ⊥ - - - ( 2 ) ; S F = F / / - F ⊥ F / / + 2 F ⊥ - - - ( 3 ) ;
D F = F / / F / / - - - ( 4 ) .
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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
CN104194398B (en) * 2014-07-28 2016-06-01 大连理工大学 One class contains fluorescence dichroic dye, its preparation method and the application of 4-(to hydroxy piperidine base)-1,8-naphthalene dintrile
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
CN109180639B (en) * 2018-09-05 2020-06-02 大连理工大学 Substituted naphthalimide derivative, preparation method and application thereof

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