Soluble Oligo- and Polythienyl Sulfides and Sulfones: Synthesis and Photophysics

Abstract

Oligomers and soluble polymers incorporating conjugated α-oligothiophene units bridged by sulfide and sulfone groups are reported. The oligomers and polymers are characterized by solution 1 H NMR spectroscopy, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, gel permeation chromatography, and photophysical methods. The energies of the frontier orbitals, the physical properties, and the optical absorption and emission of these oligomers and polymers were found to be dependent on the oxidation state of the bridging sulfur.

Selective removal of toxic organic dyes using Trӧger base-containing sulfone copolymers made from a metal-free thiol-yne click reaction followed by oxidation

“…The oxidation of thioether copolymers into their corresponding sulfone derivatives has proven to be an effective technique to increase the polarity of the resulting copolymers 53 and bestow them with improved thermal, mechanical, and electrical properties. 54–56 Copolymers bearing sulfone groups are widely utilized in fuel cells, 57 organic light emitting diodes (OLEDs), 54,58 chemosensors, 59 proton exchange, 60 organic solvent nanofilters, 61 and gas separation membranes.…”

Controlling ultralong room temperature phosphorescence in organic compounds with sulfur oxidation state

“… 25,26 The concept of tuning the electronics of a species by varying the sulfur oxidation state has since been applied to various molecular systems including oligomers, polymers and metal complexes. 27–32 …”

“…25,26 The concept of tuning the electronics of a species by varying the sulfur oxidation state has since been applied to various molecular systems including oligomers, polymers and metal complexes. [27][28][29][30][31][32] In the bridged terthiophene compounds, the bridging sulfur lone pairs (n(S)) are low in energy compared to the p HOMO of terthiophene, and thus do not participate signicantly in the low-lying excited states. Their involvement is indirect, through the screening effect of the lone pairs.…”

Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State

“…(Hetero)aromatic sulfoxides (SO) and sulfones (SO 2 ), the oxidized analogs of the corresponding sulfides (S), have recently been investigated as low molecular weight and polymeric materials in optoelectronic devices, such as: organic light-emitting diodes [1-8], solar cells [9,10], chemosensors [11][12][13], photosensitizers [14], photoreactive inks [15], redox switches [16] and as compounds exhibiting other interesting electronic and photophysical properties [17][18][19][20][21]. They have also been reported as useful pharmaceuticals [22,23] and agrochemicals [24].…”