title: New anthracene-based Schiff bases: Theoretical and experimental investigations of photophysical and electrochemical properties.
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 and13C), 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 (Eg) 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.
authors.affiliation: Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
authors.forename: Danuta
authors.initials: D
authors.lastname: Sek
authors.affiliation: Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
authors.forename: Mariola
authors.initials: M
authors.lastname: Siwy
authors.affiliation: Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
authors.forename: Marzena
authors.initials: M
authors.lastname: Grucela
authors.affiliation: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
authors.forename: Grzegorz
authors.initials: G
authors.lastname: Małecki
authors.affiliation: Faculty of Chemical Engineering and Technology Cracow University of Technology, 24 Warszawska Str., 31-155 Krakow, Poland.
authors.forename: Elżbieta M
authors.initials: EM
authors.lastname: Nowak
authors.affiliation: Institute of Physics, Cracow University of Technology, 1 Podchorazych Str., 30-035 Krakow, Poland.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Lewinska
authors.affiliation: Institute of Physics, Cracow University of Technology, 1 Podchorazych Str., 30-035 Krakow, Poland.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Santera
authors.affiliation: 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.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Laba
authors.affiliation: 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.
authors.forename: Mieczyslaw
authors.initials: M
authors.lastname: Lapkowski
authors.affiliation: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
authors.forename: Sonia
authors.initials: S
authors.lastname: Kotowicz
authors.affiliation: 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.
authors.forename: Ewa
authors.initials: E
authors.lastname: Schab-Balcerzak
keywords: DFT calculations; Electrochemistry; Photoluminescence; Schiff bases; Thermotropic liquid crystals