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Intermolecular Association of an Oblong Shape-persistent Macrocycle and Refunctionalization of Folding ortho-Phenylene Oligomers

Chu, Meng
http://orcid.org/0000-0002-9504-3761
http://rave.ohiolink.edu/etdc/view?acc_num=miami1468959764

Abstract Details

2016, Doctor of Philosophy, Miami University, Chemistry and Biochemistry.
This dissertation contains two main parts. The first part presents the synthesis, characterization, and aggregation properties of new tetrabenzo[18]cyclyne(TBCs) macrocycles. The second part is focused on a new synthetic method for ortho-phenylene oligomers, which can be used for refunctionalization in the future. Chapter 1 provides an overview of cross-conjugated systems (their synthesis and applications, such as self-assembled nanostructures and liquid crystals), macrocycles with cross-conjugated subunits (TBCs), the synthesis and applications of polyphenylenes, and the folding of ortho-phenylenes. The previously developed synthesis of both TBCs and ortho-phenylenes that were built upon in this dissertation are described. Chapter 2 presents the synthesis and characterization of new shape-persistent macrocycles comprising two 2,3-triphenylene and phthalimide moieties bridged by meta-phenylene ethynylenes. The results demonstrate that bridged macrocycles can be efficiently synthesized. The TBCs did not show any evidence of liquid crystal phases by differential scanning calorimetry or polarized optical microscopy. The phthalimide and alkyloxytriphenylene macrocycles are therefore not suitable compounds for liquid crystal materials. Chapter 3 describes the photophysical properties and solution-phase aggregation behavior of the triphenylene TBCs synthesized in chapter 2. Experimental and computational modeling results indicate that this macrocycle was present as a stacked dimer in solution and that steric interactions and aromatic stacking controlled the geometry of the dimer. Chapter 4 describes new synthetic routes toward methoxy-substituted ortho-phenylene oligomers and the experimental conditions for the esterification and click reaction which are useful for the future refunctionalization. The results demonstrate that the new synthetic route shortens the number of synthetic steps; the starting material for refunctionalization has been prepared.
C. Scott Hartley (Advisor)
Hong Wang (Committee Chair)
Michael Novak (Committee Member)
David Tierney (Committee Member)
Jason Berberich (Committee Member)
Organic Chemistry
intermolecular association, macrocycle, ortho-Phenylene

Recommended Citations

Citations

  • Chu, M. (2016). Intermolecular Association of an Oblong Shape-persistent Macrocycle and Refunctionalization of Folding ortho-Phenylene Oligomers [Doctoral dissertation, Miami University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=miami1468959764

    APA Style (7th edition)

  • Chu, Meng. Intermolecular Association of an Oblong Shape-persistent Macrocycle and Refunctionalization of Folding ortho-Phenylene Oligomers. 2016. Miami University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=miami1468959764.

    MLA Style (8th edition)

  • Chu, Meng. "Intermolecular Association of an Oblong Shape-persistent Macrocycle and Refunctionalization of Folding ortho-Phenylene Oligomers." Doctoral dissertation, Miami University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=miami1468959764

    Chicago Manual of Style (17th edition)

miami1468959764
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© 2016, all rights reserved.
This open access ETD is published by Miami University and OhioLINK.