Date of Award

Spring 1-1-2016

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry

First Advisor

Josef Michl

Second Advisor

Tarek Sammakia

Third Advisor

David Walba


The present work is directed toward the synthesis of small chromophores capable of exhibiting singlet fission which can be utilized for application in solar cells to increase efficiency. Singlet fission is a process by which an excited chromophore shares its excitation energy with a neighboring ground state chromophore and they both are converted into triplet excited states.1,2 The chromophores under investigation are based on the structure of 2,5- diketopiperazines and their derivatives. The synthesis of 3,6-dibromo-1,4-dimethyl-2,5- diketopiperazine, which is the precursor to the desired biradicaloid species, was achieved successfully. The final reduction to give the biradicaloid species and an alternate route to get to the biradicaloid involving pyrazine derivatives were also attempted. The synthesis of derivatives with tert-butyl groups on the ring were attempted. The synthesis of 3,6-di-tertbutyl-piperazine- 2,5-dione, was achieved successfully and it was fully characterized. The subsequent methylation reaction was attempted.