Date of Award

Fall 2010

Project Type


Program or Major


Degree Name

Master of Science

First Advisor

Glen Miller


The Synthesis of Dibenzo anthracenes 3, 7-diphenyldibenzo[a,h] anthracene (1) and 3,6-diphenyl-9-methoxydibenzo [a,j] anthracene ( 2) as well as a phenyl substituted picene (3) was attempted utilizing an original, generic, scheme. An Umpolung reaction between a 1,3-dithiane and a variety of dibromomethyl benzene hubs was performed to generate the carbon framework of 1, 2 and 3. Deprotection of the thioacetal groups yielded a carbonyl product which upon Grignard addition and dehydration could potentially be converted to the desired product. The proposed synthetic design allows for a variety of substitution patterns about the parent PAHs, without adding synthetic steps.