Date of Award

Summer 8-1-2018



Degree Type


Degree Name

Master of Science in Chemical Sciences (MSCB)



Committee Chair/First Advisor

Daniela Tapu

Committee Member

Christopher Alexander

Committee Member

Heather Abbott-Lyon


While early efforts have been made to explore the chemistry of neutral multitopic nonchelating N-heterocyclic carbenes (NHCs), limited progress has been made in the development of their anionic counterparts. This thesis describes the synthesis and characterization of a novel trianionic NHC. The corresponding thione was generated through an NMR experiment of the free carbenes with an excess of sulfur. The utility of this novel triscarbene as a ligand in organometallic chemistry has been proven by the construction of homotrimetallic systems. The resulting zwitterionic metal complexes of type [(MPPh)3(NHC)] (M = Au or Ag) have been fully characterized by spectroscopic techniques, as well as elemental analysis. To our knowledge, this NHC is the first trisanionic Cerberus-type NHC to be synthesized and incorporated into organometallic complexes. With its unique topological properties, this system has the potential to serve as the foundation for the preparation of novel metal−organic frameworks such as supramolecular cages and organometallic polymers, systems not accessible with the current arsenal of neutral trisNHCs. Further studies directed at the construction of such supramolecular systems are under way in our laboratory.