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Conjugated backbone doped zwitterionic polyfluorene vinylene and preparation and application

A polyfluorene, ionic technology, applied in the direction of instruments, analytical materials, measuring devices, etc., can solve the problem of a single light-emitting area, achieve wide application prospects, improve the problem of cell membrane adsorption, and improve the effect of detection sensitivity

Active Publication Date: 2018-09-21
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Moreover, most of the water-soluble polyfluorene vinylenes studied in the past are polymers formed by two monomers, with a single light-emitting area, most of which are concentrated in the blue light area, and less in the red / near-infrared light area (600-1000nm).

Method used

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  • Conjugated backbone doped zwitterionic polyfluorene vinylene and preparation and application
  • Conjugated backbone doped zwitterionic polyfluorene vinylene and preparation and application
  • Conjugated backbone doped zwitterionic polyfluorene vinylene and preparation and application

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Experimental program
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Embodiment 1

[0036] Prepare monomers (1) and (2) by the following method, feed (1), (2) and (3) according to the material ratio of 1:1.25:0.25, and then in Pd(OAc) 2 / P(o-tolyl) 3 The three are coupled through the Heck reaction under catalysis, and after 12 hours of reaction, a neutral 4,7-bis(thiophen-2 base)-2,1,3-benzothiadiazole group doped water-soluble Polyfluorene vinylene P1; further quaternization reaction with methyl iodide for 3 days to obtain cationic 4,7-bis(thiophen-2 base)-2,1,3-benzothiadiazole group doping Water-soluble polyfluorene vinylene P1'; finally, the carboxylate hydrolysis reaction was carried out with trifluoroacetic acid for 24 hours to obtain zwitterionic 4,7-bis(thiophen-2 base)-2,1,3-benzothio Oxadiazole group doped water-soluble polyfluorene vinylene P1".

[0037]

[0038]

Embodiment 2

[0040] Same as Example 1, prepare monomer (2), synthesize monomer (4) by the following method, feed (4), (2) and (3) according to the ratio of substance to 1:1.25:0.25, and then in Pd(OAc) 2 / P(o-tolyl) 3 The three are coupled through the Heck reaction under catalysis, and after 12 hours of reaction, a neutral 4,7-bis(thiophen-2 base)-2,1,3-benzothiadiazole group doped water-soluble Polyfluorene vinylene P2 was further quaternized with methyl iodide for 3 days to obtain cationic 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole group doping Water-soluble polyfluorene vinylene P2'; finally add 1,4-butane sultone and react for 3 days to obtain zwitterionic 4,7-bis(thiophen-2-yl)-2,1,3-benzene Thiadiazole group doped water-soluble polyfluorene vinylene P2".

[0041]

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Abstract

The invention discloses a conjugated backbone doped zwitterionic polyfluorene vinylene and preparation and application. The preparation comprises the following steps of: taking dibromofluorene derivative (A monomer), dienyl benzene derivative (B monomer) and dibromoaromatic heterocyclic structure (C monomer) doped with a small amount of narrow band gap, adopting a three-component polymerization method of A+B+C to carry out the Heck reaction of the organic metal catalysis, obtaining a neutral polymer, and obtaining the conjugated backbone doped zwitterionic water-soluble polyfluorene vinylene subjected to the reaction of quaternary and / or acid ester hydrolysis and the like. The synthesis method is simple, and the ratio type fluorescence emission can be achieved with improved detection sensitivity; and the red / near-infrared emission can be achieved, and the fluorescence biological imaging effect can be improved. The zwitterionic structure is beneficial to the endocytosis of the cells, which can effectively improve the adsorption of the material by the cell membrane, so that the better biological imaging effect can be achieved.

Description

technical field [0001] The invention belongs to the technical fields of chemistry, biosensing and fluorescent imaging materials, and specifically relates to a water-soluble zwitterionic water-soluble polymer with alternating fluorenyl groups and vinyl groups as conjugated main chains and doped with a small amount of aromatic heterocycles. Preparation of substances and their applications in chemical / biological sensing and fluorescent bioimaging. Background technique [0002] In the past ten years, the application of water-soluble conjugated polymers in the fields of information technology such as chemical and biological sensing has attracted more and more extensive and eager attention. These compounds combine the excellent optoelectronic properties of traditional conjugated polymers with the water solubility of polyelectrolytes. On the one hand, as conjugated polymers, they generally have strong light-absorbing properties in the ultraviolet-visible region and have the proper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12G01N21/64
CPCC08G61/126C08G2261/124C08G2261/143C08G2261/145C08G2261/146C08G2261/18C08G2261/3142C08G2261/3223C08G2261/413C08G2261/522C08G2261/70C08G2261/72C08G2261/94G01N21/6428
Inventor 黄艳琴陈昊赵永康江荣翠刘兴奋范曲立黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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