CN106278939A - The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless - Google Patents

The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless Download PDF

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Publication number
CN106278939A
CN106278939A CN201610657255.4A CN201610657255A CN106278939A CN 106278939 A CN106278939 A CN 106278939A CN 201610657255 A CN201610657255 A CN 201610657255A CN 106278939 A CN106278939 A CN 106278939A
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China
Prior art keywords
organic
glassless
aggregate material
fluorescence
metachroic
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Pending
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CN201610657255.4A
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Chinese (zh)
Inventor
苏纪宏
王震强
丁戈
高放
李红茹
张胜涛
罗自萍
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Chongqing University
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Chongqing University
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Priority to CN201610657255.4A priority Critical patent/CN106278939A/en
Publication of CN106278939A publication Critical patent/CN106278939A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Luminescent Compositions (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless；Its chemical general formula is: wherein in structural formula, R is: hydrogen, oxygen methyl, N, N dimethyl, N, N diethyl, cyano group, nitro, chloro etc..Above-mentioned organic molecule at good solvent (such as N, N dimethylformamide) and the mixed solvent of not good solvent (such as water) in, organic aggregation is obtained, it is thus achieved that the fluorescence of Glassless occurs variable color after being greatly enhanced by solvent-induced mode.

Description

The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless
Technical field
The invention belongs to organic nano material technical field, the Fluorescence Increasing particularly to a class Glassless is metachroic The preparation of organic aggregate material and application thereof.
Background technology
At present, with fluorescence organic molecule as target compound, the organic nano material prepared by the way of aggregation inducing Material has good potential using value in terms of optical sensing and imaging biological cells.But by the way of aggregation inducing, There is variable color, particularly bore hole after fluorescence can be occurred to be obviously enhanced it is observed that such process in organic material, does not the most appoint What invents report.
Summary of the invention
The purpose of the present invention is contemplated to fill up the deficiency of above-mentioned background technology, invents the Fluorescence Increasing of a class Glassless Metachroic organic aggregate material, its chemical general formula is:
Wherein in structural formula, R is: hydrogen, oxygen methyl, N, N-dimethyl, N, N-diethyl, cyano group, nitro, chloro.
Accompanying drawing explanation
Fig. 1. in examples of implementation 1,3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-stilbene solutions system is purple at 365nm Fluorescence picture under outer light-illuminating, under different assemble index sections.
Fig. 2. the organic nano that in examples of implementation 1 prepared by 3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-stilbene gathers Collection material under different assemble index sections, the surface topography map seen by scanning electron microscope (SEM).
Fig. 3. in examples of implementation 2,3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-dimethyl-stilbene is molten Liquid system fluorescence picture under 365nm UV illumination is penetrated, under different assemble index sections.
Fig. 4. 3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-dimethyl-stilbene system in examples of implementation 2 Standby organic nano aggregate material under the different time periods, the surface topography map seen by scanning electron microscope (SEM).
Fig. 5. in examples of implementation 2,3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-diethyl-stilbene is molten Liquid system fluorescence picture under 365nm UV illumination is penetrated, under different assemble index sections.
Fig. 6. 3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-diethyl-stilbene system in examples of implementation 2 Standby organic nano aggregate material under the different time periods, the surface topography map seen by scanning electron microscope (SEM).
Detailed description of the invention
The present invention is further illustrated below in conjunction with examples of implementation and accompanying drawing
Embodiment 1
3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-stilbene
In the mixed solvent of optimum (such as DMF) and not good solvent (such as water), obtain by the way of autohemagglutination is induced Organic aggregation of 3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-stilbene, and the significantly increasing of Glassless fluorescence Colourshifting process occurs after Qiang, and above-mentioned organic aggregation system, when 3min, observes solution almost under the uviol lamp that wavelength is 365nm There is no the enhancing of fluorescence；After placing 20min, solution presents faint yellow, and after placement 50min, solution is glassy yellow, after placing 2h, has Machine aggregation solution system is become luminous in pure blue by Yellow luminous and can be kept stable, as shown in Figure 1 always.
By the organic nano level aggregate material that placed 50min and 12h of above-mentioned preparation, pass through scanning electron microscope (SEM) the pattern picture of the nanoscale aggregate material of above-claimed cpd, the as shown in Figure 2 (scanned picture of a:50min have been obtained； The picture of the scanning of b, c:12h).
Embodiment 2
3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-dimethyl-stilbene
In the mixed solvent of optimum (such as DMF) and not good solvent (such as water), obtain by the way of autohemagglutination is induced Organic aggregation of 3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-dimethyl-stilbene, and Glassless Colourshifting process occurs after being greatly enhanced of fluorescence, and above-mentioned organic aggregation solution system, when 3min, is 365nm's at wavelength The solution enhancing almost without fluorescence is observed under uviol lamp；After placing 20min, solution presents faint yellow, places solution after 50min In glassy yellow, after placing 2h, organic aggregation solution system is become luminous in pure blue by Yellow luminous and can be protected always Keep steady fixed, as shown in Figure 3.
By the organic nano level aggregate material that placed 50min and 12h of above-mentioned preparation, pass through scanning electron microscope (SEM) the pattern picture of the nanoscale aggregate material of above-claimed cpd, the as shown in Figure 4 (scanned picture of a:50min have been obtained； The picture of the scanning of b, c:12h).
Embodiment 3
3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-diethyl-stilbene
In the mixed solvent of optimum (such as DMF) and not good solvent (such as water), obtain by the way of autohemagglutination is induced Organic aggregation of 3-(2 '-HYDROXY-PHENYL-METHYL-imido grpup)-4 '-N, N-diethyl-stilbene, and Glassless Colourshifting process occurs after being greatly enhanced of fluorescence, and above-mentioned organic aggregation solution system, when 3min, is 365nm's at wavelength The solution enhancing almost without fluorescence is observed under uviol lamp；After placing 20min, solution presents faint yellow, places solution after 50min In glassy yellow, after placing 2h, organic aggregation solution system is become luminous in pure blue by Yellow luminous and can be protected always Keep steady fixed, as shown in Figure 5.
By the organic nano level aggregate material that placed 50min and 12h of above-mentioned preparation, pass through scanning electron microscope (SEM) the pattern picture of the nanoscale aggregate material of above-claimed cpd, the as shown in Figure 6 (scanned picture of a:50min have been obtained； The picture of the scanning of b, c:12h).

Claims (3)

1. the metachroic organic aggregate material of the Fluorescence Increasing of a class Glassless；Its chemical general formula is:
Wherein in structural formula, R is: hydrogen, oxygen methyl, N, N-dimethyl, N, N-diethyl, cyano group, nitro, chloro etc..
The stilbene analog derivative organic nano of 3 upper hydroxyl-phenyl-imido grpups the most as claimed in claim 1 is assembled The preparation method of material is as follows:
In the mixed solvent of optimum (such as DMF) and not good solvent (such as water), obtain causing by the way of solvent-induced The metachroic organic aggregate material of Fluorescence Increasing of Glassless.
3. organic compound fluorescence intensity in the collected state as claimed in claim 1 is greatly enhanced, and occurs glimmering simultaneously Phototropic.
CN201610657255.4A 2016-08-11 2016-08-11 The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless Pending CN106278939A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610657255.4A CN106278939A (en) 2016-08-11 2016-08-11 The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610657255.4A CN106278939A (en) 2016-08-11 2016-08-11 The metachroic organic aggregate material of Fluorescence Increasing of one class Glassless

Publications (1)

Publication Number Publication Date
CN106278939A true CN106278939A (en) 2017-01-04

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085189A2 (en) * 2004-03-08 2005-09-15 Medical Research Council Analogues of congo red and evaluation of their anti-prion activity
CN101602821A (en) * 2009-07-13 2009-12-16 重庆大学 Contain synthetic and application to the visible light photosensitizer with conjugated structure schiff base type of hydroxyl
CN101602819A (en) * 2009-07-13 2009-12-16 重庆大学 Contain the synthetic and application of the visible light photosensitizer with conjugated structure schiff base type of adjacent hydroxyl
CN105111102A (en) * 2015-07-20 2015-12-02 浙江工业大学 Cyanostilbene derivative, preparation method and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085189A2 (en) * 2004-03-08 2005-09-15 Medical Research Council Analogues of congo red and evaluation of their anti-prion activity
CN101602821A (en) * 2009-07-13 2009-12-16 重庆大学 Contain synthetic and application to the visible light photosensitizer with conjugated structure schiff base type of hydroxyl
CN101602819A (en) * 2009-07-13 2009-12-16 重庆大学 Contain the synthetic and application of the visible light photosensitizer with conjugated structure schiff base type of adjacent hydroxyl
CN105111102A (en) * 2015-07-20 2015-12-02 浙江工业大学 Cyanostilbene derivative, preparation method and application thereof

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Application publication date: 20170104