The synthesis and characterization of benzodifuran and naphthodifuran based conjugated materials for use in organic photovoltaics
Muller, Evan Wayne
MetadataShow full item record
Among the many donor material building blocks for organic electronics, the benzodichalcogens and naphthodichalcogens perform near the top and most widely reported within the literature. While extensive work is described on the thiophene containing versions of these polymeric materials, relatively minimal research is reported on their furan-based chalcogen analogs due to limited synthetic approaches available to the monomers. Herein, I describe the synthesis and characterization of several naphthodifurans that demonstrate the potential of this new family of organic electronic materials. Utilizing a succinct synthetic route, a series of naphthodifuran based co-polymers were synthesized to compare to both benzodifuran- and naphthodithiophene-based materials to assess their strengths and weaknesses as donor-materials within organic photovoltaic devices. The modularity and economic attractiveness of the starting materials for the naphthodifurans offers the potential for the synthesis of several new materials based on this electron rich monomer, with potential target compounds being conjugated polymer donors as well as small-molecule acceptors for organic photovoltaics and organic field-effect transistors. The synthesis of the naphthodifuran-based materials relied on the method of a direct-(hetero)arylation polymerization, which is rapidly becoming the preferred synthetic tool for preparing organic semiconducting materials as a replacement for traditional cross-coupling reactions. Through extensive reaction screening, a broadly applicable method was developed to afford naphthodifuran-based materials possessing differing electron-acceptor co-monomers. Further establishing the substrate tolerance of the developed catalytic system is underway to further expand the scope of naphthodifuran-based organic semiconducting materials and gain additional insight into their performance in device applications. Organic photovoltaic devices were fabricated and characterized to determine their performance and to refine our molecular design for future materials based on these components within organic photovoltaics as well as other organic electronic applications. Further investigation into the morphological behavior, optoelectronic characteristics, and optimization of the device fabrication process are underway to better understand the molecular design necessary to improve these materials in device applications.
RightsAttribution-NonCommercial-ShareAlike 4.0 International