Date Approved


Degree Type

Open Access Thesis

Degree Name

Master of Science (MS)

Department or School


Committee Member

Vance Kennedy, PhD, Chair

Committee Member

Timothy Friebe, PhD

Committee Member

Maria Milletti, PhD


Ring enlargement syntheses of axially substituted boron subphthalocyanine and boron subnaphthalocyanine were investigated. The trihexylsiloxy derivatives of subphthalocyanine and subnaphthalocyanine were synthesized. These derivatives were then used in the ring-enlargement trials. Symmetrical and asymmetrical ring-enlargement reactions were carried out in a mixture of toluene and dimethylsulfoxide at room temperature. This study represents the first synthesis of boron subphthalocyanine with trihexylsiloxy group in the axial position and the first investigation into the ring enlargement of boron subnaphthalocyanine in which the axial ligand is a trihexylsiloxy group. Precipitates were formed, and it is believed that the precipitates are the metalfree ring-enlarged products. Characterization by UV-Vis and high resolution mass spectroscopy offer evidence that three of the four reactions were successful.

Included in

Chemistry Commons