Synthesis, Characterization, and Reactivity of Cross-Conjugated Frameworks

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Hamilton, V. (2018). Synthesis, Characterization, and Reactivity of Cross-Conjugated Frameworks. Unc Charlotte Electronic Theses And Dissertations.
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Abstract

ABSTRACTVICTORIA LEIGH HAMILTON. Synthesis, Characterization, and Reactivity of Cross-Conjugated Frameworks. (Under the direction of MARKUS ETZKORN)Molecules with cross-conjugated -systems possess unique structures and reactivity due to their distinctive form of conjugation that fundamentally differs from the isomeric through conjugated systems by atom connectivity. Many of the organic compounds that played a vital role in the development of industrial organic chemistry are cross-conjugated systems or were transformed to cross-conjugated organic salts (e.g., dyes such as indigo). Our larger goal to synthesize novel cross-conjugated frameworks with potential for biological or materials applications, depended on a preparative scale synthesis of necessary precursors. We prepared a small library of arene-substituted isoindanone derivatives that necessitated optimization of synthetic routes according to electronic demands of the individual systems. Reproducible routes were actualized to afford multigram quantities of these compounds as the necessary precursors to the polycyclic scaffolds targeted herein. Through this project we have established reliable protocols to novel isoindenone dimers that are synthetically intriguing substrates, which may be utilized to further investigate the electronic structure of their fleeting-intermediate monomers. Other intermediates, i.e. dibenzo[b,e]fulvalenes, have provided access to novel bimetallic complexes through ligand association reactions with appropriate transition metal carbonyl moieties. The introduction of arene substituents that are electron-donating or electron-withdrawing provided electronic contrast between these structures.

Details
Author

Hamilton, Victoria

Title

Synthesis, Characterization, and Reactivity of Cross-Conjugated Frameworks

Physical Description

1 online resource (181 pages) : PDF

Date

2018

Degree Granting Institution

University of North Carolina at Charlotte

Abstract

ABSTRACTVICTORIA LEIGH HAMILTON. Synthesis, Characterization, and Reactivity of Cross-Conjugated Frameworks. (Under the direction of MARKUS ETZKORN)Molecules with cross-conjugated -systems possess unique structures and reactivity due to their distinctive form of conjugation that fundamentally differs from the isomeric through conjugated systems by atom connectivity. Many of the organic compounds that played a vital role in the development of industrial organic chemistry are cross-conjugated systems or were transformed to cross-conjugated organic salts (e.g., dyes such as indigo). Our larger goal to synthesize novel cross-conjugated frameworks with potential for biological or materials applications, depended on a preparative scale synthesis of necessary precursors. We prepared a small library of arene-substituted isoindanone derivatives that necessitated optimization of synthetic routes according to electronic demands of the individual systems. Reproducible routes were actualized to afford multigram quantities of these compounds as the necessary precursors to the polycyclic scaffolds targeted herein. Through this project we have established reliable protocols to novel isoindenone dimers that are synthetically intriguing substrates, which may be utilized to further investigate the electronic structure of their fleeting-intermediate monomers. Other intermediates, i.e. dibenzo[b,e]fulvalenes, have provided access to novel bimetallic complexes through ligand association reactions with appropriate transition metal carbonyl moieties. The introduction of arene substituents that are electron-donating or electron-withdrawing provided electronic contrast between these structures.

Genre

masters theses

Subjects--Topics

Chemistry
Chemistry, Organic

Degree

M.S.

Keywords

Cross-Conjugation
Dendralene
Dibenzofulvalene
Isoindenone
Synthesis

Subject Area

Chemistry

Advisor(s)

Etzkorn, Markus

Committee Members

Ogle, Craig
Bejger, Christopher
Shafer, Douglas

Degree Note

Thesis (M.S.)--University of North Carolina at Charlotte, 2018.

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Rights Holder Information

Copyright is held by the author unless otherwise indicated.

Identifier

Hamilton_uncc_0694N_11949

Permalink

http://hdl.handle.net/20.500.13093/etd:39