CN102746492A - Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof - Google Patents

Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof Download PDF

Info

Publication number
CN102746492A
CN102746492A CN201210210185XA CN201210210185A CN102746492A CN 102746492 A CN102746492 A CN 102746492A CN 201210210185X A CN201210210185X A CN 201210210185XA CN 201210210185 A CN201210210185 A CN 201210210185A CN 102746492 A CN102746492 A CN 102746492A
Authority
CN
China
Prior art keywords
alkyl
group
aryleneethynylene
substance
soluble
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201210210185XA
Other languages
Chinese (zh)
Inventor
黄艳琴
任厚基
欧阳浪
刘兴奋
黄维
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanjing Post and Telecommunication University
Nanjing University of Posts and Telecommunications
Original Assignee
Nanjing Post and Telecommunication University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nanjing Post and Telecommunication University filed Critical Nanjing Post and Telecommunication University
Priority to CN201210210185XA priority Critical patent/CN102746492A/en
Publication of CN102746492A publication Critical patent/CN102746492A/en
Pending legal-status Critical Current

Links

Images

Landscapes

  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

The invention relates to a conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and a preparation method thereof. The water-soluble conjugated polymer is obtained through an A+B+C three-component polymerization method; an organic metal catalytic reaction is carried out; and the conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) is synthesized. The polymerization reaction adopts m-diiodobenzene and its derivatives (A), other dialkynyl substituted phenyl-containing and 9,9 disubstituted fluorenyl aromatic structures (B), and some dialkynyl substituted heterocyclic aryl structures (C) as monomers; the amounts of the monomers meet that the sum of the amounts of substance of B and C equals the amount of substance of A, and the amount of substance of C is less than or equal to 30% of the amount of substance of A. The characteristics are applicable to the design of diversified detection schemes, can improve detection sensitivity, meet the diversified demand of detection objects, and thus provide the materials with wide application prospects in the aspect of chemical/biological sensing detection.

Description

Adulterated polygonal line type water-soluble aryleneethynylene of a kind of conjugated main chain and preparation method thereof
Technical field
The invention belongs to chemical/biological sensing material technical field; Be specifically related to one type water miscible be conjugated main chain with alternative aromatic base and ethynyl, and the preparation of the broken-line type aryleneethynylene of a small amount of heterocyclic aryl that mixes and in the application of chemical/biological context of detection.
Background technology
Soluble conjugated polymer mainly is meant the conjugated polymers that contains the ionic functional group side chain; Caused the concern that People more and more is extensive and fervent in recent ten years, this mainly is because some unique photoelectric properties that they demonstrate can obtain diversified application in areas of information technology such as chemical/biological fluorescence senses of new generation.This compounds combines the excellent photoelectric property of traditional conjugated polymers and water solubility of polyelectrolyte characteristics.On the one hand, as conjugated polymers, they generally have very strong photo absorption performance in the ultraviolet-visible district, and have the character of " molecular wire ", promptly electronics or energy can be on conjugated main chain fast transferring.On the other hand; They mainly realize water-soluble through on the side chain of conjugated system, articulating the wetting ability ionic functional group; Ionic functional group can with other charge species generation electrostatic interaction; Therefore can detect micro substance in the surrounding environment through electronics between polymkeric substance and the oppositely charged quencher or energy transfer, and electronics or energy delocalization on whole polymer chain very easily, the quenching of fluorescence signal is exaggerated.Utilize these characteristics, on quencher, introduce the specific recognition group of various materials to be detected, through observe Quenching of fluorescence or recover just can be easy realization to the highly sensitive detection of multiple organic and inorganic and biomolecules.Nobel chemistry Prize winner A. J. Heeger in 2000, it is that sensing material has been carried out preliminary exploration in the bio-sensing field that the research group of G. C. Bazan and F. Wudl etc. has begun with the soluble conjugated polymer.
The soluble conjugated polymer of having developed at present mostly is a linear molecule with regard to the main chain configuration, the molecular studies of broken-line type structure less relatively.There is angle in the arylene acetylene in the water-soluble poly of linear structure even the unique cylindrical electronic cloud of acetylene bond also makes between adjacent phenyl rings, this has just been avoided also being unlikely to the quick delocalization of electronics on conjugated chain had a negative impact.This helps the fluorescence sense effect of research material.Through the substituted phenyl ring monomer in position between water-soluble poly is introduced in to arylene acetylene main chain, can obtain polygonal line type water-soluble aryleneethynylene.Between a position substituted benzene ring monomeric introducing this molecular backbone chain can be rotated relatively more freely, have bigger conformational freedom, help fully interacting with material to be detected; And; In the aqueous solution, trend towards taking place intramolecular fold, form and the natural biological macromole, like similar helical conformations such as DNA; Or approaching spiral conformation, these all are that the linear pattern water-soluble aryleneethynylene is in the not available advantage of chemical/biological sensory field.
But the polygonal line type water-soluble aryleneethynylene of past research mostly is the polymkeric substance that two kinds of monomers form, and light-emitting zone is single, and major part concentrates on blue region, is unfavorable for to the diversified detection scheme of different detection object designs.Therefore, the present invention introduces heterocyclic aryl in the aryleneethynylene molecular backbone chain as one of monomer, obtains the adulterated polygonal line type water-soluble aryleneethynylene of a series of conjugated main chain.This polymkeric substance not only has the advantage of broken-line type aryleneethynylene in the past; And result of study shows; Induce through some ambient conditions and can make this base polymer generation FRET; Thereby show a plurality of light-emitting zones, can be luminous like diazosulfide doping water-soluble aryleneethynylene at blue light and green glow zone, and selenole doping water-soluble aryleneethynylene can be luminous at blue light and ruddiness zone.These characteristics can be used for designing diversified detection scheme, can improve detection sensitivity, and satisfy the diversified demand of detected object, thereby make this type material that the potential wide application prospect arranged aspect the chemical/biological sensing detection.
Summary of the invention
Technical problem:The objective of the invention is to propose adulterated polygonal line type water-soluble aryleneethynylene of a kind of conjugated main chain and preparation method thereof, and propose its application in the chemical/biological context of detection.
Technical scheme:The adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain of the present invention has following molecular formula:
Figure 273596DEST_PATH_IMAGE001
Wherein, R and two alkynyls lay respectively between three of phenyl ring on the position;
Ar is that phenyl, 9,9 two replaces a kind of in the fluorenyls;
Ar ' is a kind of in diazosulfide group, the selenole group;
Polymerization degree n is the natural number greater than 1,0.7≤x＜1,0＜y≤0.3, and x+y=1;
R, R ', R " be selected from Wasserstoffatoms H, R respectively 1R 2R 3R 4N +Or R 5In the group any; R wherein 1, R 2, R 3, R 4, R 5Be respectively a kind of in alkyl, alkoxyl group, the ester group group.
Wherein:
A. when Ar ' was the diazosulfide group, wherein two kinds of typical structures were following:
When a1. Ar was phenyl, two alkynyls laid respectively at the C of Ar 1And C 4On the position, R ' and R " lay respectively at the C of phenyl 2And C 5On the position, all be Wasserstoffatoms H, the structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
Figure 673485DEST_PATH_IMAGE002
The structure I
A2. when Ar be 9,9 two when replacing fluorenyls, two alkynyls of Ar lay respectively on 2,7 of fluorenes, R ' and R " all be positioned on 9 of fluorenyl R ' and R " structure identical, be R 1R 2R 3R 4N +, R 1, R 2, R 3And R 4Be alkyl; The structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
Figure 427814DEST_PATH_IMAGE003
The structure II
B. when Ar ' was the selenole group, wherein two kinds of typical structures were following:
When b1. Ar was phenyl, two alkynyls laid respectively on 1,4 of Ar, R ' and R " lay respectively on 2,5 of phenyl, all be Wasserstoffatoms H, the structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
Figure 695985DEST_PATH_IMAGE004
The structure III
B2. when Ar be 9,9 two when replacing fluorenyls, two alkynyls of Ar lay respectively on 2,7 of fluorenes, R ' and R " all be positioned on 9 of fluorenyl R ' and R " structure identical, be R 1R 2R 3R 4N +, R 1, R 2, R 3And R 4Be alkyl.The structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
The structure IV
The preparation method of the adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain of the present invention adopts the catalytic Sonogashira polyreaction of organo-metallic; Through the earlier synthetic neutral conjugation polymkeric substance of the three component polymeric methods of A+B+C; Wherein, A be between diiodo-benzene and verivate thereof, B is that the substituted phenyl, 9,9 two that contains of diynyl replaces the fluorenyl monomers; C is adulterated diynyl substituted heterocycle aryl monomer; The amount of substance sum of monomers B and C equals the amount of substance of monomer A, and the amount of substance of C is less than or equal to 30% of A amount of substance, and the neutral polymer for preparing obtains the adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain through quaterisation again.
Beneficial effect:In the present invention, heterocyclic aryl is introduced in the aryleneethynylene molecular backbone chain as one of monomer, obtained the adulterated polygonal line type water-soluble aryleneethynylene of a kind of conjugated main chain.This polymkeric substance not only has the advantage of the water-soluble broken-line type aryleneethynylene of two components after deliberation, and induces through some ambient conditions and can make this kind polymkeric substance generation FRET, thereby shows a plurality of light-emitting zones.These characteristics can be used for designing diversified detection scheme, can improve detection sensitivity, and satisfy the diversified demand of detected object, thereby make this type material that the potential wide application prospect arranged aspect the chemical/biological sensing detection.
Description of drawings
Fig. 1. the uv-absorbing and the fluorescence emission spectrum of polygonal line type water-soluble polyhenylene acetylene.
Fig. 2. the uv-absorbing and the fluorescence emission spectrum of the adulterated polygonal line type water-soluble polyhenylene of diazosulfide acetylene.
Embodiment
Adopt the catalytic Sonogashira polyreaction of organo-metallic to prepare neutral polymer, obtain the adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain through quaterisation again, the molecular structure of compound is following:
Wherein, R and two alkynyls lay respectively between three of phenyl ring on the position; Ar is that phenyl, 9,9 two replaces a kind of in the fluorenyls; Ar ' is a kind of in diazosulfide group, the selenole group; Polymerization degree n is the natural number greater than 1,0.7≤x＜1,0＜y≤0.3, and x+y=1; R, R ', R " be selected from the following groups any respectively: Wasserstoffatoms H, R 1R 2R 3R 4N +Or R 5Here R 1, R 2, R 3, R 4, R 5Be respectively a kind of in the following groups: alkyl, alkoxyl group, ester group.
In the invention, when Ar was phenyl, two alkynyls of Ar laid respectively on 1,4 of phenyl, R ' and R " lay respectively on 2,5 of phenyl, Ar ' is a kind of in diazosulfide group, the selenole group.
Among the present invention, when Ar is 9,9 two when replacing fluorenyls, two alkynyls of Ar lay respectively on 2,7 of fluorenes, R ' and R " all be positioned on 9 of fluorenyl R ' and R " structure identical, Ar ' is a kind of in diazosulfide group, the selenole group.
In order to understand content of the present invention better, further specify the present invention through concrete embodiment below, but can not limit scope of the present invention with this.
Embodiment 1:
Prepare monomer 1 (3,5-diiodo acid-N, N-diethylammonium ethamine ester), monomer 2 (1 through following method; 4-diynyl benzene) and monomer 3 (4; 7-diynyl-2,1,3 diazosulfides); Monomer 1, monomer 2 and monomer 3 are fed intake for 1:0.8:0.2 by the amount of substance ratio, then at Pd (PPh 3) 4Through the Sonogashira reaction three's coupling is got up under/CuI the catalysis; React after 1 day; Drop into and the identical iodobenzene of monomer 1 amount of substance, reacted again 2 hours, promptly obtain neutral broken-line type polyhenylene acetylene; Further carry out quaterisation, obtain the adulterated polygonal line type water-soluble polyhenylene of diazosulfide acetylene with methyl iodide.
Figure 546632DEST_PATH_IMAGE006
?
Figure 352914DEST_PATH_IMAGE007
Embodiment 2:
With embodiment 1, preparation monomer 1 (3,5-diiodo acid-N, N-diethylammonium ethamine ester); With following method synthetic obtain monomer 4 (2,7-diynyl-9,9-two [6 '-(N; The N-DIETHANOL AMINE) hexyl] fluorenes) and monomer 5 (4,7-diynyl-2,1; 3 selenoles), monomer 1, monomer 4 and monomer 5 are fed intake for 1:0.8:0.2 by the amount of substance ratio, then at Pd (PPh 3) 4Through the Sonogashira reaction three's coupling is got up under/CuI the catalysis; React after 1 day; Drop into and the identical iodobenzene of monomer 1 amount of substance, reacted again 2 hours, promptly obtain neutral broken-line type and gather fluorenes support acetylene; Further carry out quaterisation, obtain the adulterated polygonal line type water-soluble of selenole and gather fluorenes support acetylene with methyl iodide.
Figure 402909DEST_PATH_IMAGE008
? 。

Claims (3)

1. adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain is characterized in that having following molecular formula:
Figure 201210210185X100001DEST_PATH_IMAGE002
Wherein, R and two alkynyls lay respectively between three of phenyl ring on the position;
Ar is that phenyl, 9,9 two replaces a kind of in the fluorenyls;
Ar ' is a kind of in diazosulfide group, the selenole group;
Polymerization degree n is the natural number greater than 1,0.7≤x＜1,0＜y≤0.3, and x+y=1;
R, R ', R " be selected from Wasserstoffatoms H, R respectively 1R 2R 3R 4N +Or R 5In the group any; R wherein 1, R 2, R 3, R 4, R 5Be respectively a kind of in alkyl, alkoxyl group, the ester group group.
2. the adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain according to claim 1 is characterized in that:
A. when Ar ' was the diazosulfide group, wherein two kinds of typical structures were following:
When a1. Ar was phenyl, two alkynyls laid respectively at the C of Ar 1And C 4On the position, R ' and R " lay respectively at the C of phenyl 2And C 5On the position, all be Wasserstoffatoms H, the structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
The structure I
A2. when Ar be 9,9 two when replacing fluorenyls, two alkynyls of Ar lay respectively on 2,7 of fluorenes, R ' and R " all be positioned on 9 of fluorenyl R ' and R " structure identical, be R 1R 2R 3R 4N +, R 1, R 2, R 3And R 4Be alkyl; The structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
Figure 201210210185X100001DEST_PATH_IMAGE006
The structure II
B. when Ar ' was the selenole group, wherein two kinds of typical structures were following:
When b1. Ar was phenyl, two alkynyls laid respectively on 1,4 of Ar, R ' and R " lay respectively on 2,5 of phenyl, all be Wasserstoffatoms H, the structure of R is R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
Figure 201210210185X100001DEST_PATH_IMAGE008
The structure III
B2. when Ar be 9,9 two when replacing fluorenyls, two alkynyls of Ar lay respectively on 2,7 of fluorenes, R ' and R " all be positioned on 9 of fluorenyl R ' and R " structure identical, be R 1R 2R 3R 4N +, R 1, R 2, R 3And R 4Be alkyl.
3.R structure be R 1R 2R 3R 4N +, R 1Be alkoxyl group, R 2, R 3And R 4Be alkyl, or the structure of R is R 1R 2R 3R 4N +, R 1Be ester group, R 2, R 3And R 4Be alkyl, its structural formula is following:
Figure 201210210185X100001DEST_PATH_IMAGE010
The structure IV
A kind of preparation method of the adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain according to claim 1 or claim 2; It is characterized in that adopting the catalytic Sonogashira polyreaction of organo-metallic; The earlier synthetic neutral conjugation polymkeric substance of three component polymeric methods through A+B+C, wherein, A be between diiodo-benzene and verivate thereof; B is the substituted phenyl, 9 that contains of diynyl; 9 two replace the fluorenyl monomer, and C is adulterated diynyl substituted heterocycle aryl monomer, and the amount of substance sum of monomers B and C equals the amount of substance of monomer A; And the amount of substance of C is less than or equal to 30% of A amount of substance, and the neutral polymer for preparing obtains the adulterated polygonal line type water-soluble aryleneethynylene of conjugated main chain through quaterisation again.
CN201210210185XA 2012-06-25 2012-06-25 Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof Pending CN102746492A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201210210185XA CN102746492A (en) 2012-06-25 2012-06-25 Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201210210185XA CN102746492A (en) 2012-06-25 2012-06-25 Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof

Publications (1)

Publication Number Publication Date
CN102746492A true CN102746492A (en) 2012-10-24

Family

ID=47027016

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201210210185XA Pending CN102746492A (en) 2012-06-25 2012-06-25 Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof

Country Status (1)

Country Link
CN (1) CN102746492A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103833983A (en) * 2012-11-27 2014-06-04 海洋王照明科技股份有限公司 Bi[3, 2-b]diselenophen-benzobis(benzoselenadiazole) copolymer and preparation method and application thereof
CN103833979A (en) * 2012-11-27 2014-06-04 海洋王照明科技股份有限公司 Bitriselenophen-benzodi(benzoselendiazole) copolymer, preparation method and application thereof
CN104311801A (en) * 2014-10-22 2015-01-28 温州大学 Water-soluble conjugated polymer of benzoselenadiazole and preparation method and application of conjugated polymer
CN104558541A (en) * 2014-12-19 2015-04-29 华南理工大学 Alkyne-ketone intermediate based conjugated high-molecular polymer as well as preparation method and application thereof
WO2018000735A1 (en) * 2016-06-28 2018-01-04 华南理工大学 Polymer containing 1,2,5-benzoselenadiazole-n-r 1-5,6-dicarboxylic acid imide and preparation and application thereof
CN108559064A (en) * 2018-03-13 2018-09-21 南京邮电大学 The amphoteric ion type polyfluorene vinylene of conjugated main chain doping and its preparation and application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101314634A (en) * 2008-07-04 2008-12-03 南京邮电大学 Polygonal line type water-soluble aryleneethynylene, preparation and application thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101314634A (en) * 2008-07-04 2008-12-03 南京邮电大学 Polygonal line type water-soluble aryleneethynylene, preparation and application thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
买丽丹•吾马尔等: "含苯并硒二唑组分的聚对苯撑乙炔类共轭聚合物的合成及性能研究", 《功能材料》, vol. 40, no. 7, 31 December 2009 (2009-12-31) *
牛俊峰等: "聚苯撑乙炔_苯并噻二唑共聚物的合成及光谱性能", 《化学学报》, vol. 63, no. 13, 31 December 2005 (2005-12-31) *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103833983A (en) * 2012-11-27 2014-06-04 海洋王照明科技股份有限公司 Bi[3, 2-b]diselenophen-benzobis(benzoselenadiazole) copolymer and preparation method and application thereof
CN103833979A (en) * 2012-11-27 2014-06-04 海洋王照明科技股份有限公司 Bitriselenophen-benzodi(benzoselendiazole) copolymer, preparation method and application thereof
CN103833983B (en) * 2012-11-27 2016-04-13 海洋王照明科技股份有限公司 And [3,2-b] two selenophens-benzo two (selenole) multipolymer and its preparation method and application
CN103833979B (en) * 2012-11-27 2016-04-13 海洋王照明科技股份有限公司 And three thiophene-benzo two (selenole) multipolymer and its preparation method and application
CN104311801A (en) * 2014-10-22 2015-01-28 温州大学 Water-soluble conjugated polymer of benzoselenadiazole and preparation method and application of conjugated polymer
CN104558541A (en) * 2014-12-19 2015-04-29 华南理工大学 Alkyne-ketone intermediate based conjugated high-molecular polymer as well as preparation method and application thereof
WO2018000735A1 (en) * 2016-06-28 2018-01-04 华南理工大学 Polymer containing 1,2,5-benzoselenadiazole-n-r 1-5,6-dicarboxylic acid imide and preparation and application thereof
US10090423B2 (en) 2016-06-28 2018-10-02 South China University Of Technology Polymer containing 1,2,5-benzoselenadiazole-N-R1-5,6-dicarboxylic acid imide and preparation method and use thereof
CN108559064A (en) * 2018-03-13 2018-09-21 南京邮电大学 The amphoteric ion type polyfluorene vinylene of conjugated main chain doping and its preparation and application
CN108559064B (en) * 2018-03-13 2020-09-29 南京邮电大学 Conjugated main chain doped zwitterionic polyfluorene vinylene and preparation and application thereof

Similar Documents

Publication Publication Date Title
CN102746492A (en) Conjugated backbone doped fold-line water-soluble poly(aryleneethynylene) and preparation method thereof
Yao et al. Supramolecular host–guest system as ratiometric Fe3+ ion sensor based on water-soluble Pillar [5] arene
WO2021136435A1 (en) Conjugated polymer donor material, and preparation method therefor and use thereof
CN102153748B (en) Hyperbranched polytriazole with aggregation induced light-emitting performance and preparation method and application of hyperbranched polytriazole
JP5792275B2 (en) Polymer material
CN1896074A (en) Fluorescent molecular probe and use for inspecting transient metal and heavy metal ion
CN1867528A (en) Compounds based on fluoranthene and use thereof
Zhang et al. Conjugated polyelectrolyte brushes with extremely high charge density for improved energy transfer and fluorescence quenching applications
CN102627776A (en) Preparation method of chiral fluorescent nanoparticle based on hyperbranched conjugated polymer
Gou et al. Pyrenyl-functionalized polysiloxane based on synergistic effect for highly selective and highly sensitive detection of 4-nitrotoluene
Goujon et al. An Imine Photocyclization as an Alternative to the Pictet–Spengler Reaction for the Synthesis of AzaBenzannulated Perylenediimide Dyes
CN105968329A (en) Polymer containing 1,2,5-benzoselenadiazole-N-R1-5,6-imide dicarboxylate, and preparation method and application thereof
CN108559064B (en) Conjugated main chain doped zwitterionic polyfluorene vinylene and preparation and application thereof
CN102660003B (en) Hyperbranched water-soluble conjugated polymer and preparation method thereof
JP2011099028A (en) New copolymer and method for producing the same
Xu et al. Multicomponent polymerization of alkynes, sulfonyl azide, and iminophosphorane at room temperature for the synthesis of hyperbranched poly (phosphorus amidine) s
CN107629047B (en) Asymmetric organic small-molecule photovoltaic material based on benzothiadiazole unit and preparation method and application thereof
WO2006060435A3 (en) Triarylamine containing polymers and electronic devices
CN102127207B (en) Polyfluorene/poly p-divinyl benzene and synthetic method thereof
Tan et al. Polyfluorene derivatives pending iridium complexes: Improved optoelectronic properties by introducing D‐A units and altering pendent mode
Chow et al. Electron‐Deficient Acridone Derivatives as a New Functional Core Towards Low‐Bandgap Metallopolyynes
CN103626405A (en) Single-layer fluorescent conjugated polymer membrane and preparation method thereof
Jessop et al. New Benzotriazole and Benzodithiophene-Based Conjugated Terpolymer Bearing a Fluorescein Derivative as Side-Group: In-Ternal Förster Resonance Energy Transfer to Improve Organic Solar Cells
Wang et al. In Situ Generation of Heterocyclic Polymers by Triple‐Bond Based Polymerizations
Huang et al. Para‐linked and meta‐linked cationic water‐soluble fluorene‐containing poly (aryleneethynylene) s: Conformational changes and their effects on iron–sulfur protein detection

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20121024