Study of poly(phenylene ethynylene)s, dendritic quenchers, and molecular beacons towards the application of a poly(phenylene ethynylene)-based biosensor

Poly(para-phenylene ethynylene)s (PPE)s are highly emissive conjugated polymers that are easily quenched by target analytes. As a result, they have been increasingly incorporated into sensing platforms, both as chemosensors and as biosensors. This thesis describes the three components necessary for a MB-based PPE biosensor, as well as preliminary work towards assembly of the components. A sensor system composed of three parts is presented: (1) a PPE with masked pendent maleimide groups for bioconjugation, (2) a dendritic quencher (DQ) that will be crucial for signal transduction, and (3) a DNA sequence known as a molecular beacon (MB) selective for Escherichia coli 0157:H7. In order to continue expanding the scope of PPEs in sensor applications, new handles are required with which to manipulate the polymers. These handles should be designed so as to tether small molecules, cross-linkers, and biomolecules, such as DNA, to the polymer. To this end, a PPE containing pendent maleimide units has been designed and synthesized. The maleimide group was protected as the Diels-Alder adduct with furan to prevent the maleimide from interfering with polymer synthesis.

Department dc:contributor.department

Massachusetts Institute of Technology. Dept. of Chemistry.

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2007

Author dc:creator

• Bailey, Ghislaine Caroline

Advisor dc:contributor.advisor

• Timothy M. Swager.

• Chemistry.

Statement dc:rights

• M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/1721.1/38616

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/38616