In the past decades, significant progress has been witnessed in azaborinine and azaborolide chemistry. The substitution of a CC-unit with a BN-unit gave rise to organic/inorganic hybrid compounds which were applied as active compounds in OLEDs and in organic field effect transistors (OFET).<br/>Since many substituted 1,2-azaborinines are not stable against air and moisture our concept is to stabilize these molecules by using highly stable polycyclic aromatic hydrocarbons and magnify the effect of the BN-substitution with observable optoelectronic properties.<br/>We present a novel synthetic route starting from a regioisomeric pure 1,7-substituted perylene diimide (PDI) which is further annelated to two BN-units forming a novel coronene diimides (CDI). Due to this bay-extension process it is facile to incorporate different (hetero)aryl groups to the PDI core giving rise to highly thermally stable BN-CDIs. We could prove that different substitution motifs at the imide-position, or at the boron or the nitrogen atom had interesting features towards its optical properties in solution and solid state.<br/>The bathochromic shift of these CDIs compared to the parent all-carbon molecules, the high molar extinction coefficient and their fluorescence properties, e.g. a small Stokes shift and high quantum yields (&gt;80%), make these molecules highly promising for optoelectronic applications. Initial results of first OLED and OFET devices will be further presented. Additionally, these BN-CDIs show a complex solvent-dependent optical behavior in the ground and excited states, which is currently under investigation and was not observed for their all-carbon congener.

Extending the bay-area: Synthesis, characterization, and application (OLED, OFET) of novel azaborinine-substituted coronene diimides

2019 Fall National Meeting

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