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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 103-118
DOI: 10.1055/s-0041-1725075
Focus Issue: Peter Bäuerle 65th Birthday
Original Article

Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers

Irina Zharinova 
a   ARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, Australia
,
Nicolau Saker Neto 
a   ARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, Australia
,
Tze Cin Owyong 
a   ARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, Australia
,
Jonathan M. White 
a   ARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, Australia
,
Wallace W. H. Wong 
a   ARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, Australia
› Author Affiliations Funding Information This work was funded by the Australian Research Council through the ARC Centre of Excellence in Exciton Science (CE170100026).
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Abstract

Oligo(p-phenylene)s with a donor phenol group and an acceptor pyridinium moiety separated by one and two p-phenylene units were synthesized by the linear iterative Suzuki–Miyaura coupling method using aryl nonaflates as effective coupling reagents. Zwitterionic forms of these push–pull molecules were generated upon deprotonation of the phenol leading to large redshifts in absorbance maxima. UV-vis absorbance studies also revealed strong dependence of the band position on solvent polarity: a smooth bathochromic shift can be observed with the decrease of the solvent polarity. The molecule with one p-phenylene bridging unit showed the strongest solvatochromic characteristics in the series, spanning the range of 167 nm while moving from polar water to less polar N,N-dimethylformamide. The magnitude of this shift was close to Reichardt's dye — one of the most solvatochromic organic dyes known.

Key words

conjugated molecules - cross-coupling - electron donor–acceptor systems - solvatochromism

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/s-0041-1725075.


Dedicated to Prof. Peter Bäuerle on his 65th birthday.


Supporting Information



Publication History

Received: 15 January 2021

Accepted: 01 February 2021

Article published online:
01 April 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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