A. Discovery of novel reactivity under the Sonogashira reaction conditions B. Synthesis of functionalized BODIPYs and BODIPY-sugar conjugates

A. During our attempts to synthesize substituted enediynes, coupling reactions between terminal alkynes and 1,2-cis-dihaloalkenes under the Sonogashira reaction conditions failed to give the corresponding substituted enediynes. Under these conditions, terminal alkynes underwent self-trimerization or tetramerization. In an alternative approach to access substituted enediynes, treatment of alkynes with trisubstituted (Z)-bromoalkenyl-pinacolboronates under Sonogashira coupling conditions was found to give 1,2,4,6-tetrasubstituted benzenes instead of Sonogashira coupled product. The reaction conditions and substrate scopes for these two new reactions were investigated. B. BODIPY core was functionalized with various functional groups such as nitromethyl, nitro, hydroxymethyl, carboxaldehyde by treating 4,4-difluoro-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene with copper (II) nitrate trihydrate under different conditions. Further, BODIPY derivatives with alkyne and azido functional groups were synthesized and conjugated to various glycosides by the Click reaction under the microwave conditions. One of the BODIPY–glycan conjugate was found to form liposome upon rehydration. The photochemical properties of BODIPY in these liposomes were characterized by fluorescent confocal microscopy.

Name thesis:degree_name

Ph.D. Chemistry

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Faculty of Mathematics and Science

Department dc:contributor.department

Department of Chemistry

Grantor

Brock University

Year dc:date.issued

2016

Author dc:creator

• Yalagala, Ravi Shekar

• enediyne
• Sonogashira coupling reaction
• BODIPY
• bromovinylboronoate
• Azide alkyne Click reaction

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/9496

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/9496