Polycyclic aromatic hydrocarbons connected with Schiff base linkers: Experimental and theoretical photophysical characterization and electrochemical properties

Danuta Sęk; Mariola Siwy; Jan Grzegorz Małecki; Sonia Kotowicz; Sylwia Golba; Elżbieta M Nowak; Jerzy Sanetra; Ewa Schab-Balcerzak

doi:10.1016/j.saa.2016.12.029

Polycyclic aromatic hydrocarbons connected with Schiff base linkers: Experimental and theoretical photophysical characterization and electrochemical properties

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Mar 15:175:168-176. doi: 10.1016/j.saa.2016.12.029. Epub 2016 Dec 21.

Authors

Danuta Sęk¹, Mariola Siwy¹, Jan Grzegorz Małecki², Sonia Kotowicz², Sylwia Golba³, Elżbieta M Nowak⁴, Jerzy Sanetra⁵, Ewa Schab-Balcerzak⁶

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 Institute of Materials Science, University of Silesia, 1 75 Pulku Piechoty Str., 41-500 Chorzow, Poland.
⁴ Faculty of Chemical Engineering and Technology, Cracow University of Technology, 24 Warszawska Str., 31-155 Krakow, Poland.
⁵ Institute of Physics, Cracow University of Technology, 1 Podchorazych Str., 30-035 Krakow, 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: eschab-balcerzak@cmpw-pan.edu.pl.

PMID: 28038374
DOI: 10.1016/j.saa.2016.12.029

Abstract

A series of polyaromatic hydrocarbons with anthracene, phenanthrene and pyrene units connected with Schiff base junctions were synthesized via condensation of p-phenylenediamine and hydrazine with selected aldehydes. The effect of both hydrocarbon structures and presence of N-N- or phenyl- linked diimines on properties of the prepared azines and azomethines was analyzed. The obtained compounds were soluble in common organic solvents and melted in the range of 226-317°C. Their photophysical and electrochemical properties were investigated by UV-vis, photoluminescence spectroscopies and cyclic voltammetry (CV), respectively. Moreover, a density functional theory (DFT) was applied for calculation of their electronic and geometric structures as well as absorption and emission spectra. Additionally, their electron acceptor activity was preliminary tested in photovoltaic experiment.

Keywords: Azines; Azomethines; DFT calculations; Electrochemistry; Photoluminescence; Schiff bases.