Due to their high hole mobility and self-assembling properties, linear acenes like anthradithiophene (ADT) have drawn a great deal of interest for use in organic field effect transistors. While the inherent charge-transport properties of linear acenes like ADT are desirable, functional groups are required in order to render them soluble and lead them to adopt crystal packing that is favorable for charge transport. Changing the chemical structure of the functional groups attached to the ADT core can dramatically change the materials electronic properties, photo-oxidative stability, solid-state molecular packing, and subsequent device performance. While a handful of alkyne functionalized ADT derivatives have been thoroughly studied, there are few examples of other functional groups reported in the literature. In order to further understand the structure-property relationship, from which these key properties are derived, a series of ADT molecules bearing ether, thioether, and acetyl-oxy functional groups with alky chains of varying length were synthesized and studied. Five new and two known solution-processable anthradithiophene molecules were synthesized, characterized, and incorporated into organic field-effect transistors. Optical and electrochemical properties of the different functional groups were compared, showing a distinct range of optical bandgaps and electrochemical properties. Through single-crystal XRD, the effect of heteroatom substitution and alkyl chain length on the molecular packing of these derivatives in the solid state was evaluated. Thin films of these materials were prepared using spin-coating or blade-coating and characterized by optical microscopy and profilometry. OFETs were then prepared using these conditions.

Effects of heteroatom functionalization on anthradithiophene: Exploring the influence of chemical structure on electronic properties, photo-oxidative stability, crystal packing, and device performance

254th National Meeting (2017)

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