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Water soluble fluorescent conjugated polymer and synthesis method thereof

A technology of conjugated polymers and synthesis methods, applied in chemical instruments and methods, luminescent materials, etc., can solve problems such as poor selectivity and poor specificity, and achieve excellent optical properties, improved rigidity, and good quenching efficiency.

Inactive Publication Date: 2011-04-27
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the pyridine functional group coordinates with metal ions, the optical or electrical properties of the molecular wire polymer will change accordingly. poor sex, poor selectivity

Method used

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  • Water soluble fluorescent conjugated polymer and synthesis method thereof
  • Water soluble fluorescent conjugated polymer and synthesis method thereof
  • Water soluble fluorescent conjugated polymer and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of raw materials:

[0025] A: Solvent preparation: (5ml of water, 7.5ml of dimethylformamide, 2.5ml of diisopropylamine) mix evenly and deoxygenate the solution with nitrogen for ten minutes;

[0026] B: In a 100ml three-necked flask, under nitrogen protection, add 0.1342g (0.21mmol) of 1,4-diiodo-2,5-dipropoxysodium sulfonate)benzene, 1,4-diynylbenzene 0.0120g (0.12mmol) g, 0.0134g (0.1mmol) of 2,6-diynylpyridine, 12mg (10.0μmol) of tetrakistriphenylphosphopalladium, CuI, 2mg (10.0μmol) under the protection of nitrogen, and then added with a syringe the above solvents;

[0027] (1) Polymerization: react at 65°C for 24 hours, the solution is dark brown, and has bright blue fluorescence under the irradiation of ultraviolet light;

[0028] (2) Centrifuge to separate impurities: after cooling to room temperature, centrifuge to remove insoluble matter;

[0029] (3) Precipitation: the solution is slowly added to 125ml of acetone / ether (75 / 50) mixed solution st...

Embodiment 2

[0032] Solvent preparation: 5ml of water, 7.5ml of DMF, 2.5ml of diisopropylamine, deoxygenated by nitrogen for ten minutes;

[0033] In a 100ml three-necked flask, under nitrogen protection, add 1,4-diiodo-2,5-dipropoxysodium sulfonate)benzene 0.0663g (0.102mmol), 2,6-diynylpyridine 0.0127g (0.10mmol), under the protection of nitrogen, tetrakistriphenylphosphopalladium 12mg (10.0μmol), CuI, 2mg (10.0μmol), the solvent was added with a syringe, and the solution was dark brown at 65°C for 24 hours. Under irradiation, there is bright blue fluorescence. After cooling to room temperature, filter to remove insoluble matter, spin the filtrate to concentrate, slowly add to 125ml high-speed stirred acetone / ether (75 / 50) mixed solution, a large amount of dark brown precipitate appears, stand still, remove the supernatant, The lower layer was centrifuged, and the solid was redissolved with a small amount of methanol, and then settled twice in the mixed solution of acetone / ether to obta...

Embodiment 3

[0038] Water 7.5ml, DMF 11.25ml, diisopropylamine 3.75ml, nitrogen deoxygenation for 10 minutes, in a 100ml three-necked flask, under the protection of nitrogen, add 1,4-diiodo-2,5-dipropoxysulfonate Sodium acid) benzene 0.2023g (0.31mmol), 1,4-diynylbenzene 0.0165 (0.16mmol) g, 2,6-diynylpyridine 0.0203g (0.16mmol), tetrakistriphenylphosphopalladium 17mg (15.0 μmol), CuI, 3 mg (15.0 μmol) under the protection of nitrogen, add the solvent with a syringe, and react at 65°C for 24 hours, the solution is dark brown, and has bright blue fluorescence under the irradiation of ultraviolet light. After cooling to room temperature, centrifuge to remove insoluble matter, slowly add the solution to 190ml of acetone / ether (115 / 75) mixture stirred at high speed, a large amount of dark brown precipitate appears, stand still, remove the supernatant, and centrifuge the lower layer , after the solid was redissolved with a small amount of methanol, it was settled twice in the mixed solution of ...

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Abstract

The invention discloses a water soluble fluorescent conjugated polymer and a synthesis method thereof. The polymer has a conjugated main chain with hydrophobicity and ionic type functional group side chains with hydrophilicity, wherein the ionic type functional group side chains with hydrophilicity are sulfonate and nitrobenzene; and the conjugated main chain introduces a single pyridine functional group. The invention introduces the single pyridine functional group at the conjugated main chain, thus being beneficial to aggregation of polymers, forming a three-dimensional structure and effectively improving the rigidity of the conjugated main chain; in addition, a pyridine ring can form complex with most of metallic ions so as to lead the polymeric molecule to have better quenching efficiency; further, the invention combines excellent optical performance of the conjugated polymer and water solubility of polyelectrolyte and provides a platform for designing a high-efficiency fluorescent probe.

Description

technical field [0001] The invention relates to a water-soluble fluorescent conjugated polymer and a synthesis method thereof. Background technique [0002] In recent years, conjugated polymers have attracted much attention as a new class of chemical and biological sensing materials. It has been widely used in light-emitting diodes, solar cells, plastic lasers and biosensors. Water-soluble conjugated polymers are conjugated polymers functionalized with ionic groups. The hydrophobic interaction of their conjugated backbone and the electrostatic interaction between hydrophilic ionic functional groups make them easy to self-assemble into various superstructures in solution. The molecular structure provides the design space and conditions for the selection of receptors. Their ionic side chains can be quenched by some oppositely charged quenchers through electron or energy transfer, and also have the molecular wire properties of conjugated polymers. Electrons or energy can move...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/02C08G61/12C09K11/06
Inventor 黄红梅胡玉琴肖毅鲁瑞梅
Owner HUNAN NORMAL UNIVERSITY
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