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Conformation and Assembly Research on Dendron Derivatives: Azobenzene Oligomers and Dendritic Peptides

Tie, Chenyang
http://rave.ohiolink.edu/etdc/view?acc_num=osu1282077432

Abstract Details

2010, Doctor of Philosophy, Ohio State University, Chemistry.
Chapter one covers latest azobenzene research. There are two parts on this review. First focuses on synthesis, conformation and photo energy transferring of azobenzene derivatives. Second part sequentially includes azobenzene application in self assembled monolayer (SAM), supramolecular chemistry, dendrimer, polymer, biomacromolecules. Alternating sequences of pyridine-2,6-dicarboxamides and meta-(phenylazo)azobenzenes have been assembled into oligomers composed of four and eight azobenzene linkages and reported in Chapter Two. Chapter Three introduced one simple method to prepare azo-bonds. Chapter Four exhibited conformational interconversion of a novel chiral pyridine derivative. Dendron peptide hybrids presented dynamic chirality transferring as a result of the formation of nanoassembly, an idea was brought about to apply this dynamic chirality, due to nanoassembly, into aqueous asymmetric catalysis. Chirality center was incorporated to these nanostructures, asymmetric organic reactions might achieve better steoroselectivity of products. The catalysis centers located at the branches of dendrons were first considered. However, aqueous solution was not previously investigated. One goal of the project is to explore asymmetric aldol reaction in aqueous solution and those results are reported in Chapter Five. On the other hand, further evaluation of catalysts depended on the possibility of incorporating these dendrons into peptides and forming nanoassembly. At this point, curiosity was aroused for the role of dendrons in assembly. In other words, how will dendron assist peptide conjugate assembly? So the first and second generations of dendrons coupled with beta sheet preferred peptides are examined in Chapter Six for exploring potential assembly. In addition to understanding the configuration of dendron in assembly, one critical goal of this work is to locate assembled peptide dendron conjugates with a minimum residue number so that the distinct role of corresponding dendron core portion can be realized. However, this approach halted as the residues was eight. As we went back to examine the original nanotube sequences, possibility of minimum residue number of peptide dendron retaining assembly properties was investigated. As presented in Chapter Seven, the shortest assembled peptide dendron conjugate was discovered. A broad structure assembly relationship (SAR) analysis was performed based on those results. The advantage of SAR is to predict reasonable nanoassembly based on existent examples and macroscopic information of conjugates, such as Circular Dichroism (CD) spectroscopy. SAR analysis based on the sign of CD signal due to chirality transferring provided reasonable peptide registry for de novo design of peptide dendron conjugates.
Jon Parquette, PhD (Advisor)
Christopher Hadad, PhD (Committee Member)
Yiying Wu, PhD (Committee Member)
449 p.
Chemistry; Materials Science; Organic Chemistry
Azobenzene; Dedron; Peptide; Nanoassembly;

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Citations

  • Tie, C. (2010). Conformation and Assembly Research on Dendron Derivatives: Azobenzene Oligomers and Dendritic Peptides [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1282077432

    APA Style (7th edition)

  • Tie, Chenyang. Conformation and Assembly Research on Dendron Derivatives: Azobenzene Oligomers and Dendritic Peptides. 2010. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1282077432.

    MLA Style (8th edition)

  • Tie, Chenyang. "Conformation and Assembly Research on Dendron Derivatives: Azobenzene Oligomers and Dendritic Peptides." Doctoral dissertation, Ohio State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=osu1282077432

    Chicago Manual of Style (17th edition)

osu1282077432
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© 2010, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.