New anthracene-based Schiff bases: Theoretical and experimental investigations of photophysical and electrochemical properties

Danuta Sek; Mariola Siwy; Marzena Grucela; Grzegorz Małecki; Elżbieta M Nowak; Gabriela Lewinska; Jerzy Santera; Katarzyna Laba; Mieczyslaw Lapkowski; Sonia Kotowicz; Ewa Schab-Balcerzak

doi:10.1016/j.saa.2016.12.013

New anthracene-based Schiff bases: Theoretical and experimental investigations of photophysical and electrochemical properties

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Mar 15:175:24-35. doi: 10.1016/j.saa.2016.12.013. Epub 2016 Dec 15.

Authors

Affiliations

¹ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
² Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
³ Faculty of Chemical Engineering and Technology Cracow University of Technology, 24 Warszawska Str., 31-155 Krakow, Poland.
⁴ Institute of Physics, Cracow University of Technology, 1 Podchorazych Str., 30-035 Krakow, Poland.
⁵ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland; Silesian University of Technology, Faculty of Chemistry, 9 Strzody Str., 44-100 Gliwice, Poland.
⁶ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland; Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland. Electronic address: ewa.schab-balcerzak@us.edu.pl.

PMID: 28011370
DOI: 10.1016/j.saa.2016.12.013

Abstract

The new Schiff bases bearing anthracene unit were synthesized from 2-aminoanthracene and various aldehydes such as: benzaldehyde, 4-(diphenylamino)benzaldehyde, 9-phenanthrenecarboxaldehyde, 9-anthracenecarboxaldehyde, and biphenyl-4-carboxaldehyde, 2-naphthaldehyde. Resulted azomethines were characterized by IR, NMR (¹H and ¹³C), elemental analysis and UV-vis spectroscopy. The imine consists of anthracene and biphenyl moieties exhibited liquid crystal properties and their nematic phase showed Schlieren texture. The photoluminescence measurements carried out in solution and in solid state as blend with PMMA revealed the ability of the imines to emission of the blue light with quantum yield efficiency in the range of 2.18-6.03% in blend. Based on the electrochemical experiment they showed value of energy gap (E_g) in the range of 2.5-2.7eV. Additionally, density functional theory (DFT) was applied for calculations of both electronic structure and spectroscopic properties of synthesized Schiff bases. Moreover, the results obtained from preliminary tests of application of the azomethines in organic photovoltaic (OPV) devices confirmed their electron acceptor character.

Keywords: DFT calculations; Electrochemistry; Photoluminescence; Schiff bases; Thermotropic liquid crystals.