Lei Cheng

Degree Name

Master of Science (MS)

Semester of Degree Completion

1994

Thesis Director

Jerry W. Ellis

Abstract

Sucrose is a material that has potential for replacing oil as an industrial feedstock, at least in some instances. A major difficulty in utilizing sucrose is the lack of regioselectivity in its reactions due to the many reactive sites on the sucrose molecule.

This research is part of an attempt to study the technique of molecular recognition in an effort to increase reaction regioselectivity. Molecular recognition by template imprinting should be a way to create a material that would "recognize" and bind to sucrose in such a way as to block certain of the hydroxyl groups on the sucrose. The strategy in this research is to use D-glucose as a template to synthesize a monomer with covalently bonded vinyl groups. The monomer would then be copolymerized with another monomer and a crosslinking agent to prepare a three dimensional polymer, incorporating the glucose template. Removal of the glucose would leave a cavity with the same stereochemical features as the glucose part of the sucrose molecule. Sucrose should then bind to the polymer cavity. The stereo location of the functional groups inside the cavity would be primarily responsible for the molecular recognition characteristics of the cavity. This method could increase the regioselectivity of some reactions of sucrose by blocking the glucose end of sucrose to permit reactions to occur on the fructose portion. Alternatively, a reaction might occur within the cavity.

Methyl 3-O-vinylbenzyl-2,4,6-tri-O-methacroyl-α-D-glucopyranoside was chosen as a possible monomer to demonstrate the execution of a regioselective reaction on the 3 position of the glucose within the polymer cavity. A partial syntheses of this monomer has been completed.

The surface of wide pore silica was coated with a fifty angstrom thick layer of the polymer described above. Studies of the cavities obtained and further investigation using HPLC and other techniques are continuing.

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