Polygonal line type water-soluble aryleneethynylene, preparation and application thereof

A water-soluble polymer and polyline technology, applied in the field of chemical/biosensing materials, can solve the problems of weakened fluorescence, insufficient interaction of biomolecules, and decreased detection sensitivity.

Inactive Publication Date: 2008-12-03
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
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Problems solved by technology

Water-soluble conjugated polymers are amphiphilic molecules, and for linear molecules with rigid structures, the result of the balance of the two forces of the hydrophobic interaction of the conjugated main chain and the hydrophilic interaction of the flexible side chains in aqueous solution is that it is easy to form an aggregated state. configuration, resulting in weakened fluorescence, decreased detection sensitivity, and inability to fully interact with biomolecules

Method used

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  • Polygonal line type water-soluble aryleneethynylene, preparation and application thereof
  • Polygonal line type water-soluble aryleneethynylene, preparation and application thereof
  • Polygonal line type water-soluble aryleneethynylene, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1: the synthesis of cationic broken-line water-soluble poly(arylene acetylene I)

[0087] (1) Synthesis of 2,4-diiodo-6-nitroaniline (compound 2)

[0088] 39.5g (0.24mol) of iodine monochloride was dissolved in 35mL of 1,2-dichloroethane, and slowly dropped into 17g (0.12mol) of 75°C 1,2-dichloroethane (150mL) solution, A reddish-brown precipitate was produced, and the stirring was continued at this temperature for 8 hours, and then cooled to room temperature. Suction filtration, the resulting solid was washed with methanol, and the product was an orange-red solid (23 g, yield 50%). Melting point: 151°C. 1 HNMR (CDCl 3 , 400MHz): δ (ppm) 8.44 (d, 1H, J = 1.9Hz), 8.13 (d, 1H, J = 2.3Hz), 6.69 (br s, 2H). C 6 h 4 I 2 N 2 o 2 Elemental analysis theoretical value: C, 18.48; H, 1.03; N, 7.18; measured value: C, 18.64; H, 1.01; N, 7.13.

[0089] (2) Synthesis of 1,3-diiodo-5-nitrobenzene (compound 3)

[0090] At 0°C, slowly add 8.4g (0.12mol) of sodium n...

Embodiment 2

[0101] Example 2: Synthesis of cationic broken-line water-soluble poly(arylene acetylene VII)

[0102] (1) Synthesis of 2,7-diiodofluorene (compound 11)

[0103] At 80°C, fluorene (2.54g, 15mmol) was dissolved in 165mL of mixed solvent (acetic acid: water: sulfuric acid = 50:4:1), and potassium iodate (1.28g, 6mmol) and iodine (4.1g, 16.3 mmol), the mixture was stirred at this temperature for 10 hours, and precipitation occurred during the reaction. After cooling to room temperature, the precipitate was collected by suction filtration, and the solid was washed with 2M sodium carbonate solution and water until the filtrate was neutral. The crude product was recrystallized from dichloromethane to obtain a pale yellow solid (4.76 g, yield 76%). Melting point: 216-217°C. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 7.87 (s, 2H), 7.70 (d, 2H, J=8.0Hz), 7.49 (d, 2H, J=8.0Hz), 3.83 (s, 2H). C 13 h 8 I 2 Elemental analysis theoretical value: C, 37.35; H, 1.93; measured value: C, 37.36; ...

Embodiment 3

[0114] Embodiment 3: Synthesis of anionic broken-line water-soluble poly(arylene acetylene II)

[0115] (1) Synthesis of m-diiodobenzene (monomer F) whose side chain end group is a sulfonic acid group

[0116] Dissolve 3.5g (0.022mol) of sodium hydroxide in 50mL of ethanol, add dropwise to 6.92g (0.02mol) of 3,5-diiodophenol (compound 5) in 50mL of ethanol solution, and stir for 1 hour. Dissolve 2.68g (0.022mol) of 1,3-propane sultone in 50mL of ethanol, add the above solution, and stir for 12 hours at a reaction temperature of 50-60°C. The crude product was obtained by suction filtration, and the solid was recrystallized from absolute ethanol and water to obtain monomer F with a yield of 56%. 1 HNMR (DMSO-d 6 , 400MHz): δ (ppm) 7.58 (s, 1H), 7.14 (s, 2H), 3.94 (t, 2H), 3.41 (t, 2H), 2.27 (m, 2H).

[0117] (2) Synthesis of broken-line water-soluble poly(arylene acetylene II)

[0118] Under the protection of nitrogen, add the mixed solvent diisopropylamine, water and N,N-di...

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Abstract

The invention belongs to the technology field of the chemo-biosensing material, particularly a preparation method of water soluble zigzag poly(arylene-ethynylene) by adopting alternate phenyl, acetenyl, and aryl as conjugated main chain, and the application in chemical and biological detection thereof. The preparation method comprises the steps as follows: subjecting m-diiodobenzene and the derivatives thereof as the raw material and other various diynyl substituted aromatic compounds to organic metal catalytic reaction for synthesizing a series of water soluble poly(arylene-ethynylene) having water soluble group in side chain and zigzag structure as conjugated main chain. Compared with the conventional linear-type water soluble conjugated polymer prepared from the m-diiodobenzene and the derivatives thereof as the raw material, the zigzag poly(arylene-ethynylene) has large conformational freedom in the main chain, which facilitates full interaction with a substance to be detected and tends to generate intramolecular fold in aqueous solution to form spiral or approximately spiral conformation and represent high-sensitivity fluorescence quenching effect, thereby the simple and rapid chemo-bioluminescent sensing detection is realized.

Description

technical field [0001] The invention belongs to the technical field of chemical / biological sensing materials, and specifically relates to a preparation method of a water-soluble poly(arylene acetylene) with alternating phenyl, ethynyl and aromatic groups as the conjugated main chain and its application in chemical / biological detection applications. Background technique [0002] Water-soluble conjugated polymers mainly refer to conjugated polymers containing ionic functional group side chains, which have attracted more and more widespread and eager attention in the past decade, mainly because of their unique photoelectric properties that can be Diversified applications in information technology fields such as new generation chemical / bioluminescence sensing. 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-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02G01N21/00
Inventor 黄维黄艳琴范曲立
Owner NANJING UNIV OF POSTS & TELECOMM
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