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Diversity Oriented Synthesis

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Front. Chem. | doi: 10.3389/fchem.2018.00579

Diversity-oriented Synthesis and Optical Properties of Bichromophoric Pyrrole-Fluorophore Conjugates

Oliver Grotkopp1,  Bernhard Mayer1 and  Thomas J. Müller1*
  • 1Institut für Organische Chemie und Makromolekulare Chemie, Heinrich Heine Universität Düsseldorf, Germany

The mild reaction conditions of the palladium-copper coupling-isomerization reaction open a highly convergent, chromogenic route to blue emissive pyrroles in the sense of a consecutive four-component reaction. By virtue of this strategy a phenol derivative can be readily accessed, which can be transformed in a level-2 transformation to a library of bichromophoric pyrrol-fluorophore conjugates by facile alkylation with fluorophore halides. The photophysics of the underlying blue emitter derivative and the conjugates is studied by absorption and emission spectroscopy, furnishing intramolecular energy transfer at short distances as well as competing fluorescence quenching. In some cases partial energy transfer results in the occurrence of dual emission, for instance seen as magenta-rose emission arising from blue and red orange luminescence. The experimental photophysical studies are rationalized by DFT and TD-DFT calculations.

Keywords: absoption, Bichromophore, DFT, emission, Energy transfer (ET) dyes, Level-2 functionalization, multicomponent reaction (MCR), pyrrole

Received: 10 Sep 2018; Accepted: 06 Nov 2018.

Edited by:

Lisa Moni, Università di Genova, Italy

Reviewed by:

Eddy Sotelo, Universidade de Santiago de Compostela, Spain
Fabio De Moliner, Queen's Medical Research Institute, University of Edinburgh, United Kingdom  

Copyright: © 2018 Grotkopp, Mayer and Müller. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence: Prof. Thomas J. Müller, Heinrich Heine Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Düsseldorf, 40225, North Rhine-Westphalia, Germany, ThomasJJ.Mueller@hhu.de