Electro-optical Properties of Neutral and Radical Ion Thienosquaraines

Vito Maltese; Sante Cospito; Amerigo Beneduci; Bruna Clara De Simone; Nino Russo; Giuseppe Chidichimo; René A J Janssen

doi:10.1002/chem.201601281

Electro-optical Properties of Neutral and Radical Ion Thienosquaraines

Chemistry. 2016 Jul 11;22(29):10179-86. doi: 10.1002/chem.201601281. Epub 2016 Jun 23.

Authors

Vito Maltese^{1

2}, Sante Cospito³, Amerigo Beneduci⁴, Bruna Clara De Simone³, Nino Russo³, Giuseppe Chidichimo³, René A J Janssen⁵

Affiliations

¹ Department of Chemistry and Chemical Technologies, University of Calabria, Via P. Bucci, Arcavacata di Rende (CS), 87036, Italy. vito.maltese@unical.it.
² Molecular Materials and Nanosystems, Institute for Complex Molecular Systems, Eindhoven University of Technology, P. O. Box 513, 5600 MB, Eindhoven, The Netherlands. vito.maltese@unical.it.
³ Department of Chemistry and Chemical Technologies, University of Calabria, Via P. Bucci, Arcavacata di Rende (CS), 87036, Italy.
⁴ Department of Chemistry and Chemical Technologies, University of Calabria, Via P. Bucci, Arcavacata di Rende (CS), 87036, Italy. amerigo.beneduci@unical.it.
⁵ Molecular Materials and Nanosystems, Institute for Complex Molecular Systems, Eindhoven University of Technology, P. O. Box 513, 5600 MB, Eindhoven, The Netherlands.

PMID: 27334359
DOI: 10.1002/chem.201601281

Abstract

Thienosquaraines are an interesting class of electroactive dyes that are useful for applications in organic electronics. Herein, the redox chemistry and electrochromic response of a few newly synthesized thienosquaraines are presented. These properties are compared to those of the commercial 2,4-bis[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl]squaraine. The stability of the radical ions formed in electrochemical processes strongly affects these properties, as shown by cyclic voltammetry, in situ spectroelectrochemistry, and quantum chemical calculations. Furthermore, all of the dyes show aggregation tendency resulting in panchromatic absorption covering the whole UV/Vis spectral range.

Keywords: aggregation; density functional calculations; electrochemistry; radical ions; squaraines.