Thioalkyl- and sulfone-substituted poly(p-phenylene vinylene)s

Abstract

Poly(p-phenylene vinylene)s (PPVs) have been studied for decades, but new applications like in bioimaging keep emerging and even simple structural variations are still waiting to be explored, as we highlight by this work.

Post-polymerisation approaches for the rapid modification of conjugated polymer properties

“…12 Sulfone-substituted polymers P25-31 prepared via post-polymerisation oxidation of sulfur atoms in polythiophenes and alkylthio-substituted polymers. [84][85][86][87][88] solution, no change in the absorption wavelengths was observed in this case, but the emission was red shifted by B80 nm, from blue to yellow.…”

“…In some more recent follow-up work, the use of DMDO to alter the photophysical properties of alkylthio-substituted conjugated polymers was demonstrated in donor–acceptor type materials ( P28–30 ) as well as alkylthio-substituted poly( p -phenylene vinylene)s P31 . 87,88…”

“…The first reaction -the oxidation of sulfur atoms in the backbone or in functional groups attached to the backbone to the corresponding sulfoxides or sulfones -has been shown to be a particularly fast and selective approach for post-polymerisation functionalisation of conjugated polymers. [84][85][86][87][88] The approach is especially useful to obtain polymers with significantly altered properties from a starting polymer in just one step, as the electron-donating sulfur is transformed into electron-withdrawing groups by the oxidation. Fig.…”

“…By making use of this post-polymerisation oxidation, n-type conjugated polymers can be obtained that may not be accessible by polymerisation of the oxidised monomer. 88 Using this approach, a continuous junction design for organic electronic devices relying on postprocessing oxidation of electron-donor polymer thin films has been proposed, as discussed in more detail below. 85 In 2014, Campos and colleagues reported the use of Rozen's reagent (HOFÁCH 3 CN) for the oxidation of thiophene in order to obtain thiophene-1,1-dioxide (TDO)-containing polymers P25.…”

Controlling the molecular weight of poly(2,5‐bis[N‐methyl‐N‐hexylamino]phenylene vinylene) using nitrobenzene as an inhibitor

“…13,14 The most commonly studied PPVs contain alkoxy-substituents on the phenylene ring, but other substituent functionalities such as thio-alkyl and amino groups have also demonstrated unique properties with promising applications. [15][16][17] Specifically, poly(2,5-bis[N-methyl-N-hexylamino]phenylene vinylene) (BAM-PPV, Scheme 1) has shown superior corrosion protection for aluminum alloys with performance matching hexavalent chromium primers in laboratory and field testing. [18][19][20][21] Therefore, BAM-PPV has potential as a low toxicity alternative to conventional yet toxic metal coatings.…”