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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Thermally Induced Silane Dehydrocoupling on Silicon Nanostructures.

Dokyoung Kim¹, Jinmyoung Joo¹, Youlin Pan²

¹Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA.

Angewandte Chemie (International Ed. in English)

|April 22, 2016

Summary

Catalyst-free grafting of organic trihydridosilanes onto porous silicon nanostructures offers a robust surface modification method. This technique yields stable, functionalized surfaces with retained photoluminescence, useful for applications like drug delivery.

Keywords:

mesoporous materials photoluminescence porous silicon quantum dots surface chemistry

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Published on: November 9, 2015

Area of Science:

Materials Science
Surface Chemistry
Nanotechnology

Background:

Porous silicon (Si) nanostructures are versatile materials with tunable properties.
Surface functionalization is crucial for tailoring Si nanostructures for specific applications.
Existing methods often require catalysts or harsh conditions, limiting their scope.

Purpose of the Study:

To develop a catalyst-free method for grafting organic trihydridosilanes onto hydrogen-terminated porous Si.
To demonstrate the versatility and stability of the modified surfaces.
To showcase the retention of intrinsic photoluminescence after grafting.

Main Methods:

Reaction of hydrogen-terminated porous Si with organic trihydridosilanes at 80°C.
Utilizing various silanes including alkyl, bromo-functional, vinyl-functional, and perfluoro-functional silanes.
Post-grafting chemical transformations of the bromo-derivative to introduce amine, azide, and alkyne functionalities.

Main Results:

Efficient grafting achieved without catalysts, showing tolerance to air and water impurities.
Modified surfaces exhibited stability in corrosive aqueous solutions and organic solvents.
Perfluoro-grafting on mesoporous Si wafers resulted in superhydrophobic surfaces (contact angle 151°).
Bromo-derivatives were successfully converted to azide, amine, and alkyne surfaces.
Antibiotic ciprofloxacin was loaded onto functionalized surfaces (35% by mass).
Photoluminescence of porous Si was retained in grafted products.

Conclusions:

Catalyst-free grafting of organic trihydridosilanes is an effective and robust method for porous Si surface modification.
The functionalized porous Si materials are stable and retain their photoluminescence.
This approach enables diverse applications, including drug delivery and the creation of superhydrophobic surfaces.