Optoelectronic engineering with organic dyes: utilizing squaraine and perylene diimide to access an electron-deficient molecule with near-IR absorption

Applying direct heteroarylation cross-coupling reactions to the synthesis of π-conjugated materials has facilitated the creation of molecular libraries in an efficient and more sustainable way than was previously possible with traditional cross-coupling methods. Utilizing this approach, we have been able to realize new compounds with tailored optoelectronic properties. In this work, we disclose the design, synthesis and characterization of an optically and electrochemically engineered molecular compound composed of a bis-indole squaraine dye flanked by N-annulated perylene diimide units to access an electron-deficient π-conjugated structure with strong light absorption ranging from the visible to near-infrared and reversible ambipolar redox behavior. Graphical Abstract