ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Abby-Jo Payne, Seth M. McAfee, and Gregory C. Welch

University of Calgary, Calgary, Canada

E-mail: Gregory.welch@ucalgary.ca

Abstract: 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.

Keywords: Organic electronics ; Near-IR optical absoprtion ; Organic dyes ; Squaraine ; Perylene diimide ; Direct (hetero)arylation cross-coupling 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0361-y

Chemical Papers 72 (7) 1629–1634 (2018)