950207-96-2Relevant academic research and scientific papers
Thiophene ring-fragmentation reactions: Principles and scale-up towards NLO materials
Lumpi, Daniel,Steindl, Johannes,Steiner, Sebastian,Carl, Victor,Kautny, Paul,Sch?n, Michael,Gl?cklhofer, Florian,Holzer, Brigitte,St?ger, Berthold,Horkel, Ernst,Hametner, Christian,Reider, Georg,Mihovilovic, Marko D.,Fr?hlich, Johannes
, p. 472 - 480 (2017)
A systematic study on the thiophene ring-fragmentation (TRF) reaction, yielding the Z-isomer of ene-yne type compounds, is presented. The investigations focus on the origins and pathways of potential side-reactions, resulting in an advanced synthetic protocol featuring enhanced selectivity and efficiency. The fragmentation threshold temperatures as well as reaction kinetics have been investigated utilizing inline infrared spectroscopy revealing unexpected results particularly concerning the reaction order (zero-order process). With regard to safety, selectivity, and up-scaling a flow-chemistry procedure for the TRF reaction has been developed. Finally, the technological relevance of the ene-yne structural motif is extended by a new design concept for NLO-chromophores showing the highest second harmonic generation efficiencies reported for these scaffolds.
The irreversible thermo-bleaching function of a photochromic diarylethene having trimethylsilyl groups
Kobatake, Seiya,Imagawa, Hiroyuki,Nakatani, Hidenori,Nakashima, Seiichiro
experimental part, p. 1362 - 1367 (2009/09/24)
A new function of a photochromic diarylethene, having trimethylsilyl groups at the reactive positions, has been developed. Upon alternating ultraviolet and visible light irradiation, the diarylethene showed photoreversible photochromism in a polymer film, as well as in solution. The colored state changed to colorless immediately upon heating at 100 °C. The colorless state, which is different from the open-ring isomer, was stable under both ultraviolet and visible light irradiation. Such photochromic materials could potentially be used in applications as secret display materials. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.
