Donor-Pi-Acceptor Fluorene Conjugates, Based on Chalcone and Pyrimidine Derivatives: an Insight into Structure-Property Relationship, Photophysical and Electrochemical Properties

J Fluoresc. 2020 Mar;30(2):419-426. doi: 10.1007/s10895-020-02516-z. Epub 2020 Feb 24.

Abstract

A small set of four new fluorenyl chromophores (5-5a-c) was accomplished by stepwise nucleophilic substitution, Friedel-Crafts acylation, Ullman coupling, aldol condensation and cyclization reactions. The fluorene moiety was substituted at 2,7,9 and 9' positions with diverse groups. The synthesized derivatives were characterized by FTIR, 1H-NMR and 13C-NMR spectroscopic techniques. The optical properties were evaluated by by UV-VIS absorption and Fluorescence studies. HOMO and LUMO energy levels were evaluated by electrochemical studies and were found at -5.37-5.83 eV and - 2.47-2.94 eV respectively with band gap energy values 2.88 to 2.91 eV. The band gap energy values suggested that these synthesized molecules can be manipulated in the designing of blue and green OLEDS. Graphical Abstract.

Keywords: Band gap energy; Fluorene conjugates; HOMO and LUMO; OLEDS; Optoelectronic properties.