Development of an Improved Synthetic Route to Triply Linked Di(Perylene Bisimides) With Varied Substituents and Their Performance as Non-Fullerene Acceptors in Polymer Photovoltaics
Polymers and High Performance Materials
A series of triply-linked perylene bisimide dimers (diPBIs) with varied solubilizing groups (short-chain aliphatic, long-chain aliphatic, and aryl) were synthesized to determine the structure-property relationships that govern their performance as non-fullerene acceptors in conventional polymer photovoltaic devices. In the synthesis of the intermediates, a new solvent and ligand system for dehalogenation of 1,6,7,12-tetrabromo-perylene bisimides to 1,12 dibromo-perylene bisimides was developed in order to access PBI systems that are not available via procedures previously reported. The new dimethylacetamide/2-picolinic acid system expands the available R-groups for inclusion on perylene bisimides that render them insoluble in the conventional DMSO/L-proline system, while providing milder conditions and higher yields. A cosolvent system of DMSO/diphenyl sulfoxide was utilized to couple the brominated perylene bisimides, allowing for direct coupling of aliphatic-substituted perylene bisimides. The resulting diPBIs showed only very small differences in optoelectronic properties, but aliphatic-substituted diPBIs provided better performance due to their better solubility and ability to form co-continuous films with the donor polymer PTB7.
Moore, L. M.,
Norman, M. B.,
Benasco, A. R.,
Richardson, J. M.,
Morgan, S. E.
(2018). Development of an Improved Synthetic Route to Triply Linked Di(Perylene Bisimides) With Varied Substituents and Their Performance as Non-Fullerene Acceptors in Polymer Photovoltaics. Synthetic Metals, 237, 56-64.
Available at: https://aquila.usm.edu/fac_pubs/15047