A Diketopyrrolopyrrole-Based Dimer as a Blue Pigment

Manuela Casutt; Benedikt Dittmar; Hanna Makowska; Tomasz Marszalek; Soh Kushida; Uwe H F Bunz; Jan Freudenberg; Daniel Jänsch; Klaus Müllen

doi:10.1002/chem.201806121

A Diketopyrrolopyrrole-Based Dimer as a Blue Pigment

Chemistry. 2019 Feb 21;25(11):2723-2728. doi: 10.1002/chem.201806121. Epub 2019 Jan 25.

Authors

Manuela Casutt^{1

2}, Benedikt Dittmar¹, Hanna Makowska³, Tomasz Marszalek⁴, Soh Kushida¹, Uwe H F Bunz^{1

5}, Jan Freudenberg^{1

2}, Daniel Jänsch^{1

2}, Klaus Müllen⁴

Affiliations

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
² InnovationLab, Speyerer Straße 4, 69115, Heidelberg, Germany.
³ Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924, Lodz, Poland.
⁴ Max-Planck-Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
⁵ Centre of Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.

PMID: 30624815
DOI: 10.1002/chem.201806121

Abstract

1,4-Diketopyrrolo[3,4-c]pyrroles (DPPs) constitute a class of hydrogen-bonded pigments covering a color range from yellow-orange to dark violet. We report facile dimerization of a Boc-substituted 3,6-dithienyl-DPP. The formed dimer shows brilliantly blue color as a result of the expansion of the chromophore. The soluble dimer acts as latent pigment and is converted to the corresponding pigment either via thermocleavage or acidic deprotection of the Boc groups. The synthesized pigment is characterized by high migrational stability in a polymer matrix and a clear blue color.

Keywords: 1,4-diketopyrrolo[3,4-c]pyrrole; blue pigment; dimerization; latent pigment; tert-butyloxycarbonyl.