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Accessing Novel Graphene Nanoribbon Architectures through Double peri-Annulations

Title: Accessing Novel Graphene Nanoribbon Architectures through Double peri-Annulations.
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Name(s): Skala, Morgan Elizabeth, author
Type of Resource: text
Genre: Text
Bachelor Thesis
Date Issued: 2020-04-14
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: Routes to construct graphene nanoribbons (GNRs) and nanographenes (NGs) from smaller polycyclic aromatic hydrocarbons (PAHs) have long been explored. Foundational work in the Alabugin group has recently culminated in the development of a double peri-annulation protocol where aromatic core precursors containing a propargylic OMe traceless directing group (TDG) are π-extended through Sn-radical promoted cyclizations. After cyclization, two Bu3Sn chemical handles are present in the products. These handles can serve for downstream PAH-extension via cross-coupling and cycloaromatization approaches. As proof-of-concept, our group has recently reported the extension of distannylpyrenes via iodination followed by double Suzuki crosscoupling with an aromatic electrophile. By mono cross-coupling of the 1,8-disubstituted-2,7 distannylpyrenes, we hypothesize that extension at one Sn at a time may be possible, allowing to further diversify the PAH library accessible for the construction of GNRs. Mono-Suzuki and Stille couplings were explored under multiple conditions with limited success due to prevalent double cross-couplings in the former and sluggish reactivity in the latter. The broad flexibility of the Bu3Sn handles allows for exploration of other approaches, for example, the borylation of the cyclized product, further cross-coupling with aryl dihalides and cycloaromatization in order to access novel GNR structures.
Identifier: FSU_libsubv1_scholarship_submission_1587398980_0995fdc0 (IID)
Keywords: polyaromatic hydrocarbons, benzannulations, graphene, alkyne, cross-coupling
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_libsubv1_scholarship_submission_1587398980_0995fdc0
Host Institution: FSU

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Skala, M. E. (2020). Accessing Novel Graphene Nanoribbon Architectures through Double peri-Annulations. Retrieved from http://purl.flvc.org/fsu/fd/FSU_libsubv1_scholarship_submission_1587398980_0995fdc0