pi-Conjugated molecules with low band gaps have been widely used as functional materials in the field of photovoltaics and bioimaging. In this work, pi-conjugated molecules with deep-red absorption activities were synthesized through a series of reactions, initially making two different indolocarbazole derived molecules; fluorinated and non-fluorinated. The indolocarbazole derivatives proceed to go through a Stille Coupling reaction followed by a borylation process using BF3. The borylation process provides the N→B coordination needed to limit the torsional motion and lower the LUMO levels of the molecules significantly, affording a narrowed optical band gap (lambdamax = 650 nm) and a low-energy emission. The strong N→B coordination interactions render the excellent stability of these conjugated molecules.

Low band gap p-conjugated molecules featuring N→B coordination

255th National Meeting (2018)

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