Synthetic Strategies Towards Pi-Extended Dithienophospholes Available for Click Chemistry

A series of highly luminescent P-acetylenyl functionalized dithieno[3,2-b:2’,3’-d]phospholes were attempted to be synthesized following the previously studied P-phenyl phosphole as a guide. The original synthesis pathway of forming the dithienophosphole scaffold first, then cross-coupling onto the 2,6-positions, then modifying the acetylene to be able to perform click chemistry saw many difficulties. An alternative route was explored where the cross-coupling reaction with a brominated bithiophene was performed first, then a ring closure reaction to form the phosphole was done. Finally, the emissive materials were able to be clicked onto benzyl azide as a proof-of-concept for an organic light-emitting polymer material for the potential application of solid-state lighting.

Name thesis:degree_name

Master of Science (MSc)

Discipline thesis:degree_discipline

Chemistry

Grantor dc:publisher.institution

Graduate Studies

Year dc:date.issued

2018

Author dc:creator

• MacLean, Liisa

Advisors dc:contributor.advisor

• Baumgartner, Thomas
• Welch, Gregory

Committee members dc:contributor.committeemember

• Sutherland, Todd
• Ling, Chang-Chun

Statement dc:rights

• University of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.

Language dc:language.iso

eng

DOI

http://dx.doi.org/10.11575/PRISM/31839

OAI identifier oai:identifier

oai:ucalgary.scholaris.ca:1880/106553