Schneider, Rebekka V.;
Waibel, Kevin A.;
Arndt, Andreas P.;
Lang, Mathias;
Seim, Rebecca;
Busko, Dmitry;
Bräse, Stefan;
Lemmer, Uli;
Meier, Michael A. R.
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Media type:
E-Article
Title:
Sequence-definition in stiff conjugated oligomers
Contributor:
Schneider, Rebekka V.;
Waibel, Kevin A.;
Arndt, Andreas P.;
Lang, Mathias;
Seim, Rebecca;
Busko, Dmitry;
Bräse, Stefan;
Lemmer, Uli;
Meier, Michael A. R.
imprint:
Springer Science and Business Media LLC, 2018
Description:
<jats:title>Abstract</jats:title><jats:p>The concept of sequence-definition in the sense of polymer chemistry is introduced to conjugated, rod-like oligo(phenylene ethynylene)s via an iterative synthesis procedure. Specifically, monodisperse sequence-defined trimers and pentamers were prepared via iterative Sonogashira cross-coupling and deprotection. The reaction procedure was extended to tetra- and pentamers for the first time yielding a monodisperse pentamer with 18% and a sequence-defined pentamer with 3.2% overall yield. Furthermore, three novel trimers with a 9<jats:italic>H-</jats:italic>fluorene building block at predefined positions within the phenylene ethynylene chain were synthesised in 23–52% overall yields. Hence, it was confirmed that a functionality of interest can be incorporated selectively at a pre-defined position of these monodisperse oligomers. All respective intermediate structures were fully characterised by proton and carbon NMR, mass spectrometry, size-exclusion chromatography, and IR spectroscopy. Additionally, thermal and optical transitions are reported for the different oligomers.</jats:p>