Aminobenzodione-based polymers with low bandgaps and solvatochromic behavior

Haichang Zhang; Saman Ghasimi; Bernd Tieke; Alexander Schade; Stefan Spange

doi:10.1039/C3PY01702H

Aminobenzodione-based polymers with low bandgaps and solvatochromic behavior†

Haichang Zhang,^a Saman Ghasimi,^a Bernd Tieke,*^a Alexander Schade^b and Stefan Spange^b

* Corresponding authors

^a Department of Chemistry, University of Cologne, Luxemburger Str.116, D-50939 Cologne, Germany
E-mail: tieke@uni-koeln.de

^b Department of Polymer Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, D-09111 Chemnitz, Germany

Abstract

Pd-catalyzed amination polymerization of deep blue aminobenzodifuranone monomer 3-(4-bromo-phenyl)-7-(4-octylaminophenyl)-benzo[1,2-b:4,5-b′]-difuran-2,6-dione (M1) is described, as well as polymerization of symmetric dibromophenyl-benzodifuranone (M2), or the corresponding dibromophenylbenzodipyrrolidone (M3) with N,N′-dialkylated phenylenediamines (M4a,b). The resulting polymers P1–3 exhibit low bandgaps (1.08–1.47 eV), broad UV/vis absorption bands (400–900 nm), and a large solvatochromic shift up to 3140 cm⁻¹ from n-hexane to hexamethylphosphoramide. Multiple linear regression analyses of [small nu, Greek, tilde] _max of the solvent-dependent solvatochromic UV/vis absorption bands of M1, P1 and P2a are presented, from which Kamlet–Taft and Catalán solvent parameters were determined. All monomers and polymers exhibit high extinction coefficients up to 8.6 × 10⁴ L mol⁻¹ cm⁻¹ and high photostability, and might be suitable for electronic applications.

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DOI: https://doi.org/10.1039/C3PY01702H
Article type: Paper
Submitted: 11 Dec 2013
Accepted: 16 Feb 2014
First published: 25 Mar 2014
This article is Open Access

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Polym. Chem., 2014,5, 3817-3823

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Aminobenzodione-based polymers with low bandgaps and solvatochromic behavior

H. Zhang, S. Ghasimi, B. Tieke, A. Schade and S. Spange, Polym. Chem., 2014, 5, 3817 DOI: 10.1039/C3PY01702H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Polymer Chemistry

Aminobenzodione-based polymers with low bandgaps and solvatochromic behavior†

Abstract

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Aminobenzodione-based polymers with low bandgaps and solvatochromic behavior

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