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Rotaxane molecular machine of naphthalimide crown ether and pH meter based on rotaxane molecular machine

A naphthalimide crown ether, molecular machine technology, applied in the field of pH meter, can solve the problems of poor repeatability of results, poor test stability, easy to contaminate samples, etc., and achieve the effect of eliminating influence and high conversion rate

Inactive Publication Date: 2014-01-29
SHANGHAI WEIKAI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The existing pH meters on the market have disadvantages such as poor repeatability of results, easy contamination of samples, long detection cycle, poor test stability, easily damaged electrodes, and low detection limits.

Method used

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  • Rotaxane molecular machine of naphthalimide crown ether and pH meter based on rotaxane molecular machine
  • Rotaxane molecular machine of naphthalimide crown ether and pH meter based on rotaxane molecular machine
  • Rotaxane molecular machine of naphthalimide crown ether and pH meter based on rotaxane molecular machine

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Experimental program
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Effect test

Embodiment 1

[0035] The disulfide bond-containing azide compound 1 involved in the present invention has a chemical formula of C 19 h 27 N 3 o 5 S 2 , the schematic diagram of its synthetic route is shown in figure 1 As shown, the specific synthesis steps are as follows:

[0036] 1.1 Synthesis of Compound 4

[0037] Add 150mL of acetonitrile, 3,5-dimethoxy-4-hydroxybenzaldehyde (5g, 0.027mol) and 1,2-dibromoethane (19.97g, 0.11mol) into a 250mL round bottom flask, and add Potassium carbonate powder (7.59g, 0.055mol) was heated and refluxed overnight. The reaction solution was poured into 500mL water, stirred for 30min, CH 2 Cl 2 (50mL×3) extraction, anhydrous Na 2 SO 4 After drying, the solvent was removed by column chromatography (SiO 2 , Petroleum ether: dichloromethane = 3: 1), to obtain 6.82 g of pure compound 4 with a yield of 86%. 1 H NMR (CDCl 3 , 400MHz, 298K): δ(ppm)=9.88(s, 1H), 7.13(s, 2H), 4.38-4.33(t, J=8.0Hz, 2H), 3.93(s, 6H), 3.64-3.59( t, J=8.0Hz, 2H).

[003...

Embodiment 2

[0045] The present invention relates to naphthalimide crown ether compound 2-naphthoimide dibenzo 24 crown 8 crown ether, and its method route schematic diagram is as follows figure 2 As shown, the specific synthesis steps are as follows:

[0046] 2.1 Synthesis of Compound 2

[0047] Add 25 mL of dry CH to a 50 mL round bottom flask 2 Cl 2 , and then sequentially add such as monoaldehyde dibenzo 24 crown 8 with NaBH 4 After reduction, the reduced product (1 g, 2.09 mmol), compound 7 (0.71 g, 2.09 mmol), DMAP (0.25 g, 2.09 mmol) and EDC·HCl (1.62 g, 8.36 mmol) were stirred overnight under argon protection. The reaction solution was poured into 100mL water and stirred for 30min, CH 2 Cl 2 (25mL×3) extraction, anhydrous Na 2 SO 4 After drying, the solvent was removed by column chromatography (SiO 2 , dichloromethane:methanol=200:1), 1.44g of compound 2 was obtained, and the yield was 86%. 1 H NMR (CDCl 3 , 400MHz, 298K): δ(ppm)=8.60(d, J=4.0Hz, 1H), 8.54(d, J=8.0Hz, 1H...

Embodiment 3

[0049] The schematic diagram of the synthetic route of the rotaxane molecular machine of compound 2-H-naphthalimide crown ether of the present invention is as image 3 As shown, it specifically includes the following steps:

[0050] 3.1 Synthesis of Compound 1-H

[0051] in dry CH 2 Cl 2 Dissolve compound 3 (153mg, 0.249mmol) and naphthalimide crown ether compound 2 (192mg, 0.249mmol) in (10mL), stir at room temperature for 30min, then add disulfide bond-containing azide compound 1 (110mg, 0.249mmol) and [Cu(CH 3 EN) 4 ]PF 6 (93mg, 0.249mmol), stirring was continued for two days. The solvent was spinned off, and column chromatography (SiO 2 , CH 2 Cl 2 : MeOH=100:1) to obtain yellow compound 1-H (50.8 mg, 67%). 1 H NMR (CDCl 3 , 400MHz, 298K): δ(ppm)=8.06(s, 1H), 7.51(s, 2H), 7.18(m, 2H), 7.01(d, J=8.0Hz, 2H), 6.90(m, 2H) , 6.79(m, 2H), 6.70(m, 2H), 6.55(s, 2H), 6.42(s, 2H), 6.24(s, 1H), 5.16(s, 4H), 5.03(s, 2H), 4.80(t, J=4.0Hz, 4H), 4.71-4.66(t, J=4.0Hz, 2H), 4....

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Abstract

The invention discloses a rotaxane molecular machine of naphthalimide crown ether and a pH meter based on the molecular machine. Structural formula of the molecular machine is represented as a formula (I) as shown in the specification. The pH meter includes a gold electrode and the rotaxane molecular machine of the naphthalimide crown ether which is adsorbed on the surface of the gold electrode to form a self-assembled monolayer. The synthesized rotaxane molecular machine of the naphthalimide crown ether is bonded with the gold electrode through a disulfide bond, to result in transfer of the molecular machine and charges on the gold electrode in a process of adding acid or alkali, thus achieving online rapid monitoring of pH value; the molecular machine can avoid accumulation of waste generated from the whole monitoring process on the monolayer, thus enhancing detection limit, sensitivity and fatigue resistance.

Description

technical field [0001] The invention belongs to the technical field of molecular machines and electrochemistry, and in particular relates to a rotaxane molecular machine of naphthalimide crown ether and a pH meter based on it. Background technique [0002] As a type of molecular machine, the rotaxane-type molecular shuttle consists of a ring molecule and a linear molecule. The linear molecule runs through the inner cavity of the ring molecule, and the large blocking groups at both ends of the linear molecule can prevent Cyclic molecules break away from linear molecules. Under the action of specific external stimuli, the ring-shaped molecule can make a reciprocating piston movement along the linear molecule between the two blocking groups. The rotaxane-type molecular shuttle is one of the ideal systems for studying the weak interaction between molecules and its controllable transformation. It provides a new model system for the study of important physical and chemical proces...

Claims

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Application Information

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IPC IPC(8): C07D409/12C07D405/12C07D339/04G01N21/64
CPCC07D339/04C07D405/12C07D409/12G01N21/6428G01N2021/6432
Inventor 虞明东周斌丁万强
Owner SHANGHAI WEIKAI CHEM
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