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p-phenyleneethynylenes carrying biologically relevant ligands

Posted on:2004-09-02Degree:Ph.DType:Thesis
University:Georgia Institute of TechnologyCandidate:Erdogan, BelmaFull Text:PDF
GTID:2461390011458380Subject:Chemistry
Abstract/Summary:
Assembly of two- or three-dimensional molecular scale building blocks into well-defined meso- and macroscopic structures and the control of their formation are main goals of nanotechnology and materials chemistry. Biological macromolecules such as proteins and nucleic acids received great interest in the last decade due to the possible ability to direct the formation of molecular architectures. Our goals for the first part at this thesis are to design and synthesize self-assembled o- and p-cyclobutadiene complexes and phenyleneethynylene oligomers (dimers through heptamers) and construct cyclic supramolecules by using DNA as a linker. To construct the desired building blocks, we used well-established phosphoramidite chemistry. This method allows the facile synthesis of oligonucleotide modified organic complexes by using any diol and the resulting complex does not interfere with the hybridization and it does not require post-synthetic modifications.; Various non-conjugated polymers with carbohydrates attached have been described but only polythiophenes and polydiacetylenes have been utilized as sugar-coated conjugated polymers. The poly(para-phenylenethynylene)s are another type of conjugated polymers that show high fluorescence in solution and solid state. These materials have been used successfully in light emitting and sensory devices, but biologically active derivatives are not known.; Carbohydrate attached PPEs are multitopic bioconjugates that could mimic cell surfaces. They have great potential for sensory applications because they will change their optical/emissive properties upon binding to bacterial/viral lectins or pathogens. The conjugated PPEs can easily carry one sugar per repeating unit and bind strongly to lectins. Upon binding, dramatic biochromism is expected, when the polymer backbone either planarizes or deplanarizes upon the binding event.; Our goals for the second part of this thesis are utilizing sugar-substituted or biologically relevant ligand substituted PPEs to detect the presence of viruses and toxins. For these purposes, various PPE derivatives have been prepared and their supramolecular and spectroscopic behaviors have been examined.
Keywords/Search Tags:Biologically
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