Benzene-Benzothiadiazole Cyclophanediene Synthesis and Ring-Opening Metathesis Polymerization

open_access
Open Access
Author:
Lussier, Holly
Area of Honors:
Chemistry
Degree:
Bachelor of Science
Document Type:
Thesis
Thesis Supervisors:
Elizabeth A Elacqua, Thesis Supervisor
Benjamin James Lear, Thesis Honors Advisor
Keywords:
ROMP
conjugated polymers
donor-acceptor polymers
regioselectivity
Abstract:
Conjugated donor-acceptor polymers are composed of alternating electron-rich (donor) and electron-deficient (acceptor) aromatic units, giving rise to organic materials that are lightweight, flexible, and tunable, which makes them promising in organic electronic applications such as photovoltaic devices and light-emitting diodes. The electronic properties of these polymers can be tuned by modifying the donor and acceptor units within the polymer backbone. Based on previous work from our group, which established that ring-opening metathesis polymerization (ROMP) of a strained donor-acceptor paracyclophanediene (pCpd) yields conjugated, sequence- controlled poly(arylenevinylene) (PAV) architectures, we aim to investigate how selective functionalization of the alkene within paracyclophanediene influences polymerization behavior. Here, we detail efforts to synthesize a functionalized paracyclophanediene scaffold and examine its reactivity toward ring-opening metathesis polymerization.