Liqiang Li

Type

Text

Type

Thesis

Advisor

Sampson, Nicole S | Lauher, Joseph | Ojima, Iwao

Date

2017-08-01

Keywords

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/11401/78231

Publisher

The Graduate School, Stony Brook University: Stony Brook, NY.

Format

application/pdf

Abstract

Linear alternating polymers have potential applications in nanoelectronics, biochemistry and catalysis. Recent progress shows that bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides and cyclohexene can copolymerize in the presence of Grubbs III catalyst to provide long alternating polymers with low dispersity. However, the preparation of the monomer amide is based on Ru-catalyzed isomerization of bicyclo[4.2.0]oct-7-ene-7-carboxamides, which increases the cost and makes it hard to scale the reaction. Therefore, a more efficient monomer synthesis method is required. This thesis describes a 6 step synthetic route that provides the bicyclo[4.2.0]oct-1(8)-ene-8-carboxamide in 18% overall yield. The route significantly reduces the monomer preparation cost to approximately $6/g, and is scalable to provide gram quantities. Further investigation of nitrile, acid, ester and aldehyde bicyclo[4.2.0] derivatives in alternating ring opening metathesis (AROMP) was undertaken. The bicyclo[4.2.0]oct-1(8)-ene-8-carboxaldehyde showed high reactivity in ring opening metathesis and AROMP reactions. Although obtaining high purity aldehyde is still an obstacle, the aldehyde moiety allows facile introduction of functional groups and side chains into polymers. | 72 pages

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