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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 184-190
DOI: 10.1055/a-1472-6806
Focus Issue: Peter Bäuerle 65th Birthday
Original Article

Reductive Coupling Synthesis of a Soluble Poly(9,10-anthrylene ethynylene)

Isabell Geisler
a   Bergische Universität Wuppertal, Macromolecular Chemistry Group (buwmakro) and Wuppertal Center for Smart Materials & Systems, Gauss-Str. 20, D-42119, Wuppertal, Germany
,
Michael Forster
a   Bergische Universität Wuppertal, Macromolecular Chemistry Group (buwmakro) and Wuppertal Center for Smart Materials & Systems, Gauss-Str. 20, D-42119, Wuppertal, Germany
,
Bujamin Misimi
b   Bergische Universität Wuppertal, Chair of Electronic Devices and Wuppertal Center for Smart Materials & Systems, Rainer-Gruentner-Str. 21, D-42119 Wuppertal, Germany
,
Jakob Schedlbauer 
c   Universität Regensburg, Institut für Experimentelle und Angewandte Physik, Universitätsstrasse 31, D-93053 Regensburg, Germany
,
Thomas Riedl 
b   Bergische Universität Wuppertal, Chair of Electronic Devices and Wuppertal Center for Smart Materials & Systems, Rainer-Gruentner-Str. 21, D-42119 Wuppertal, Germany
,
John M. Lupton 
c   Universität Regensburg, Institut für Experimentelle und Angewandte Physik, Universitätsstrasse 31, D-93053 Regensburg, Germany
,
Ullrich Scherf 
a   Bergische Universität Wuppertal, Macromolecular Chemistry Group (buwmakro) and Wuppertal Center for Smart Materials & Systems, Gauss-Str. 20, D-42119, Wuppertal, Germany
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Abstract

A fully soluble poly(9,10-anthrylene ethynylene), poly[2,6-(2-octyldecyl)-9,10-anthrylene ethynylene] PAAE, with moderate degrees of polymerization Pn of ca. 10 is generated in a reductive, dehalogenative homocoupling scheme, starting from a 2,6-dialkylated 9,10-bis(dibromomethylene)-9,10-dihydroanthracene monomer and n-BuLi/CuCN as the reducing agent. PAAE shows surprisingly broad and unstructured absorption and photoluminescence emission bands with peaks at 506 nm and 611 nm, respectively, both in chloroform solution. The long absorption tail ranging into the 600–700 nm region and the large Stokes shift points to a high degree of geometrical disorder in the arrangement of the 9,10-anthrylene chromophores along the distorted polymer backbone. This disorder is borne out in the unusually strong wavelength dependence of fluorescence depolarisation, both with regards to the excitation and the emission wavelengths. Picosecond fluorescence depolarisation spectroscopy provides clear evidence for the presence of orthogonal transition dipole moments, presumably arising from the off-axis transition of the anthracene unit and the on-axis transition of the polymer backbone. Intramolecular energy relaxation then gives rise to the observed fluorescence depolarization dynamics.

Key words

conjugated polymers - poly(arylene ethynylene)s - reductive coupling - fluorescence anisotropy

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/a-1472-6806.


Dedicated to Professor Peter Bäuerle on the occasion of his 65th birthday.


Supporting Information



Publication History

Received: 13 January 2021

Accepted: 17 March 2021

Accepted Manuscript online:
01 April 2021

Article published online:
28 June 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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