Condensation is the most ubiquitous method for synthesizing commodity polymers, conjugated polymers, oligomers, and the small molecules used as organic semiconductors in light-emitting diodes (OLED)s and photovoltaic cells (PVC)s. Tetraaryl-benzo[1,2-d:4,5-d’]bisoxazole (BBO) are generally synthesized using bis-o-aminophenols and aromatic dicarboxylic acid chlorides in mixtures containing trimethylsilyl polyphosphate/o-dichlorobenzene, polyphosphoric acid, or phosphorus pentoxide/methanesulfonic acid and heated to temperature above 200°C. These reaction conditions are both caustic and harsh limiting the scope of substituents that could be substituted on the BBO structural unit. Previously, our group reported that orthoesters can be used for the synthesis of functional BBO’s under mild conditions. Unfortunately, the methods for the synthesis of the requisite orthoester are limited in scope and number. The goal for this project is twofold. First, I developed and employed a versatile synthetic method for making orthoesters that uses economically obtainable starting materials and has milder reactions conditions, Figure 1. I utilized these synthons as building blocks for new BBO-based organic electronic materials 5.

Synthesis of aryl-orthoesters: New building blocks for organic semiconductors

256th National Meeting (2018)

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