Type
Text
Type
Dissertation
Advisor
Fowler, Frank W | Goroff, Nancy | Lauher, Joseph W | Rudick, Jonathan | Kim, Sung Won.
Date
2015-08-01
Keywords
crystal design, hydrogen bond, macrocycle, polydiacetylene, topochemical polymerization | Organic chemistry
Department
Department of Chemistry.
Language
en_US
Source
This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree.
Identifier
http://hdl.handle.net/11401/77124
Publisher
The Graduate School, Stony Brook University: Stony Brook, NY.
Format
application/pdf
Abstract
This dissertation is focused on the polymerization of diacetylenes through a single-crystal-to- single-crystal transition, which requires a prearrangement of the diacetylene monomers in space. In the first project, we developed a supramolecular host-guest strategy to control the interactions among monomers. the host N,N'-oxalyldiglycine and the guest hexa-2,4-diyne-1,6-diyl dinicotinate have been synthesized and characterized. Their polydiacetylenic co-crystal structure has been revealed by single crystal X-ray diffraction. The decomposition of the co-crystal polymer, which could lead to a new polymer, has also been investigated by various characterization methods. The second project of this research is the development of a general strategy for synthesizing supramolecular organic nanotubes via a macrocyclic architecture. A series of macrocyclic diacetylene monomers with different functional groups have been designed and synthesized successfully. Extensive studies have focused on the enhancement of their stability and solubility. The correct packing of the macrocycles has been achieved via pi-pi stacking. We have obtained the desired tubular structures as shown in the crystal structures. Finally, studies on the effects of hydrogen bonding for the formation of crystal structures have also been explored. | 268 pages
Recommended Citation
Liu, Bo, "Design and Preparation of Polydiacetylenes Using Supramolecular Chemistry" (2015). Stony Brook Theses and Dissertations Collection, 2006-2020 (closed to submissions). 2960.
https://commons.library.stonybrook.edu/stony-brook-theses-and-dissertations-collection/2960