Conjugated small molecules and polymers continue to attract attention for organic electronic applications. These materials are generally classified as either hole transport (p-type) or electron transport (n-type) systems. This presentation will focus on two classes of heterocycle that exhibit n-type behavior, the benzothiaphospholes and the thiophene 1,1-dioxides. The benzothiaphospholes consist of a P=C bond within the conjugated architecture and were synthesized from 1-mercapto-2-phosphinobenzene. The electrochemical and photophysical properties of the benzothiaphospholes will be presented and some of these molecules exhibit reversible 1-electron reductions. Aryl substituted thiophene 1,1-dioxides were prepared using Stille cross-coupling chemistry and these sulfone heterocycles luminesce in solution. The oxidation and reduction potentials of the thiophene 1,1-dioxides can be readily tuned using electron donating and electron withdrawing aryl substituents.

Synthesis and photophysical properties of benzothiaphospholes and thiophene 1,1-dioxides

247th National Meeting (2014)

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