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

Study of modulating opto-electrochemical properties in Suzuki coupled phenazine derivatives for organic electronics

Deepali N. Kanekar, Purav M. Badani, and Rajesh M. Kamble

Department of Chemistry, University of Mumbai, Mumbai, India

E-mail: kamblerm@chem.mu.ac.in

Received: 15 February 2021  Accepted: 1 July 2021

Abstract:

In this work, five 3,6,11-trisubstituted-dibenzo[a,c]phenazine (2–6) derivatives were synthesized by employing Palladium-catalyzed Suzuki–Miyaura ‘C–C bond’ coupling reaction and characterized. Absorption spectra of 2–6 show the formation of charge-transfer complexes. Dyes exhibit blue-green fluorescence with emission maxima 434–506 nm in various solvents and neat solid film. To elucidate AIE phenomenon, photophysical properties of dye 2 and 3 in different THF/water mixture were studied. The HOMO and LUMO energy level were found in the range of − 6.38 to − 6.82 eV and − 3.67 to − 3.75 eV with an electrochemical bandgap of 2.71–3.08 eV. The HOMO and LUMO distribution in molecules were further studied by DFT/TD–DFT calculations. Herein, characteristic blue emission, comparable energy levels with n-type materials, and good thermal stability of derivatives make them a potential candidate for their application in optoelectronics.

Graphic abstract

Keywords: Donor–acceptor system; Suzuki–Miyaura coupling; Photophysical studies; Aggregation-induced emission (AIE); HOMO and LUMO energy level; n-type materials

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01772-y

Chemical Papers 75 (11) 5945–5961 (2021)