Click polymerization: Synthesis of novel σ-π conjugated organosilicon polymers

Poly[silylene-1,4-phenylene-(1,2,3-triazol-4-yl)-1,4-phenylene]s were prepared via step-growth Click coupling polymerization of bis(p-ethynylphenyl)silanes and 1,4-diazidobenzene. The organosilicon units in the backbones may contribute to an electronic communication among the π-conjugated units and improve the solubility of the polymers. Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR) were used to confirm the polymers structure. The UV–vis absorption wavelength of silicon-containing compounds red-shifted ca. 15 nm when compared with the compounds without silicon atoms. The fluorescence emission of polymers in CHCl3 solutions was observed in visible blue region (ca. 440 nm), and the intensity and quantum yield (Φ) were enhanced due to the influence of σ-π interaction. The results of the absorption and emission supported the weak σ-π conjugation between the silylene and aromatic segments, and these polymers can be potentially applied in organic light emitting devices (OLEDs).

Graphical abstractPoly[silylene-1,4-phenylene-(1,2,3-triazol-4-yl)-1,4-phenylene]s (P1, P2) were prepared from bis(p-ethynylphenyl)silanes and 1,4-diazidobenzene by Click polymerization. The fluorescence spectrum of the products in dilute CHCl3 solutions exhibit emission in visible blue region (ca. 440 nm) with moderate quantum yields (Φ＞0.4), showing these polymers may be potentially applied as emission materials in OLEDs.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► The σ-π conjugated organosilicon polymers were obtained via Click polymerization. ► The polymers emit in visible blue region with moderate quantum yields. ► The polymers could be used as potential optical materials in OLEDs.