Nanoporous organosilicas as pre-concentration materials for sensors

• US 7,705,062 B2
• Filed: 01/31/2006
• Issued: 04/27/2010
• Est. Priority Date: 09/08/2005
• Status: Expired due to Fees

• Current Assignee: The Government Of The United States Of America, As Represented By The Secretary Of The Navy
• Original Assignee: the united states of america as represented by the secretary of the navy
• Inventors: Trammell, Scott, Zeinali, Mazyar, Charles, Paul, Markowitz, Michael
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LOEWE, ROBERT S
• Application Number:
  US11/307,286
• Publication Number:
  US 20070054418A1
• Time in Patent Office: 1,547 Days
• Field of Search: 521/100, 521/110
• US Class Current: 521/99
• CPC Class Codes: B01J 20/268 Polymers created by use of a template, e.g. molecularly imprinted polymers
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C09D 183/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence
• CPC Class Codes: Y10S 436/815 Test for named compound or class of compounds

Abstract

A molecularly imprinted material made from polymerizing a monomer having the structural formula (OR)₃Si—B-A-B—Si(OR)₃. A is a divalent organic group, B is a saturated or unsaturated divalent hydrocarbon group or a covalent bond, and R is an independently selected saturated or unsaturated monovalent hydrocarbon group. A preconcentrator having: a container comprising in inlet and an outlet and the above material within the container. The inlet is capable of allowing a fluid to enter the container. The outlet is capable of being coupled to a sensor and of allowing the fluid to exit the container.

Claims

1. A molecularly imprinted material comprising pores or channels having surfaces that include a plurality of molecularly imprinted cavities;

wherein the material comprises a polymer made from polymerizing a monomer having the structural formula (OR)₃Si—

B-A-B—

Si(OR)₃;

wherein A is a divalent organic group;

wherein each B is an independently selected saturated or unsaturated divalent hydrocarbon group or a covalent bond;

wherein each R is an independently selected saturated or unsaturated monovalent hydrocarbon group; and

wherein the material is made by a method comprising;

combining a solvent, the monomer, and a surfactant coupled to an imprint group;

wherein the imprint group is decylaminetrinitrobenzene;

wherein molecules of the surfactant self-assemble to form at least one supramolecular structure having a surface and wherein the imprint groups are exposed on the surface; and

wherein the supramolecular structure serves as a template for the organizing of molecules of the monomer along the surface of the supramolecular structure and around the exposed imprint groups;

polymerizing the monomer to form a solid structure having a surface topography complementary to the surface topography of the supramolecular structure and having indentations complementary to the shape of the exposed imprint groups; and

removing the supramolecular structure from the solid structure.

2. The material of claim 1, wherein polymerizing the monomer comprises copolymerizing the monomer with one or more additional monomers.

3. The material of claim 1, wherein the material further comprises one or more pendant functional groups.

4. A preconcentrator comprising:

a container comprising in inlet and an outlet;

wherein the inlet is capable of allowing a fluid to enter the container; and

wherein the outlet is capable of being coupled to a sensor; and

the material of claim 1 within the container.

5. A method of detecting an analyte comprising:

providing the preconcentrator of claim 4;

providing a sensor coupled to the outlet;

moving a fluid suspected of containing the analyte into the inlet and in contact with the material;

contacting the material with a solvent capable of removing the analyte from the material; and

contacting the sensor with the solvent.

6. The material of claim 1, wherein the monomer is 1,4-bis(trimethoxysilyl)benzene or 1,4-bis(trimethoxysilylethyl)benzene.

7. A preconcentrator comprising:

a container comprising in inlet and an outlet;

wherein the inlet is capable of allowing a fluid to enter the container; and

wherein the outlet is capable of being coupled to a sensor and of allowing the fluid to exit the container; and

a material within the container;

wherein the material comprises a polymer made from polymerizing a monomer having the structural formula (OR)₃Si—

B-A-B—

Si(OR)₃;

wherein A is a divalent organic group;

wherein each B is an independently selected saturated or unsaturated divalent hydrocarbon group or a covalent bond; and

wherein each R is an independently selected saturated or unsaturated monovalent hydrocarbon group;

wherein the material is made by a method comprising;

combining a solvent, the 1,4-bis(trimethoxysilyl)benzene, and a surfactant coupled to an imprint group;

wherein the imprint group is decylaminetrinitrobenzene;

wherein molecules of the surfactant self-assemble to form at least one supramolecular structure having a surface and wherein the imprint groups are exposed on the surface; and

wherein the supramolecular structure serves as a template for the organizing of molecules of the 1,4-bis(trimethoxysilyl)benzene along the surface of the supramolecular structure and around the exposed imprint groups;

polymerizing the 1,4-bis(trimethoxysilyl)benzene to form a solid structure having a surface topography complementary to the surface topography of the supramolecular structure and having indentations complementary to the shape of the exposed imprint groups; and

removing the supramolecular structure from the solid structure.

8. The preconcentrator of claim 7, wherein polymerizing the monomer comprises copolymerizing the monomer with one or more additional monomers.

9. The preconcentrator of claim 7, wherein the material further comprises one of more pendant functional groups.

10. A method of detecting an analyte comprising:

providing the preconcentrator of claim 7;

providing a sensor coupled to the outlet;

moving the fluid suspected of containing the analyte into the inlet and in contact with the material;

contacting the material with a solvent capable of removing the analyte from the material; and

contacting the sensor with the solvent.

11. The preconcentrator of claim 7, wherein the monomer is 1,4-bis(trimethoxysilyl)benzene or 1,4-bis(trimethoxysilylethyl)benzene.

12. A method of making a material having a molecularly imprinted surface comprising:

providing a solvent, a monomer, and a surfactant coupled to an imprint group;

wherein the imprint group is decylaminetrinitrobenzene;

wherein the monomer has the structural formula (OR)₃Si—

B-A-B—

Si(OR)₃;

wherein A is a divalent organic group;

wherein each B is an independently selected saturated or unsaturated divalent hydrocarbon group or a covalent bond; and

wherein each R is an independently selected saturated or unsaturated monovalent hydrocarbon group;

combining the solvent, the monomer, and the surfactant;

wherein molecules of the surfactant self assemble to form at least one supramolecular structure having a surface and wherein the imprint groups are exposed on the surface; and

wherein the supramolecular structure serves as a template for the organizing of molecules of the monomer along the surface of the supramolecular structure and around the exposed imprint groups;

polymerizing the monomer to form a solid structure having a surface topography complementary to the surface topography of the supramolecular structure and having indentations complementary to the shape of the exposed imprint groups; and

removing the supramolecular structure from the solid structure.

13. The method of claim 12, wherein polymerizing the monomer comprises copolymerizing the monomer with one or more additional monomers.

14. The method of claim 12, wherein the surfactant is C₁₈H₃₇(OCH₂CH₂)₁₀OH.

15. The method of claim 12, wherein the material further comprises one of more pendant functional groups.

16. The method of claim 12, wherein the monomer is 1,4-bis(trimethoxysilyl)benzene or 1,4-bis(trimethoxysilylethyl)benzene.