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Photochromism of dihydroindolizines. Part XV: Synthesis and photophysical properties of dihydroindolizine photoswitches bearing a conjugated aryleneethynylene tripodal linker system

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Abstract

Different photochromic dihydroindolizines (DHIs) bearing conjugated aryleneethynylene tripodal linker systems were synthesized using several Sonogashira coupling reactions. The spirocyclopropene precursors incorporating different acetylenic bridge moieties at the 2-position of the fluorene moiety were synthesized via chemical and photochemical routes. Multiaddressable photochromic properties of the DHI derivatives substituted in the fluorene (region A) and pyridazine (region C) parts were studied. Optimization of the formation of the DHIs was also done by applying different palladium-mediated Sonogashira coupling reactions. Irradiation of the photochromic DHIs with polychromatic light led to colored betaines which undergo thermal 1,5-electrocyclization. The kinetics of the thermal 1,5-electrocyclization were studied by using a multichannel FT–UV–Vis spectrophotometer. A pronounced effect on the kinetic behavior of the 1,5-electrocyclization process of the betaines was observed by changing substitution from non-substituted to dimethyl-substituted pyridazines. Photodegradation experiments and the bleaching and fading cycles revealed high photostability of the betaines under investigation. These properties of betaines of tripodal linker conjugates will help these materials to find applications.

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Acknowledgments

The authors are highly indebted to the Taibah University (project no. 479/430) and Alexander von Humboldt foundation (AvH) for financial support of this work. Many thanks to Professor Dr Heinz Dürr (University of Saarland, Saarbrücken, Germany), Professor Dr Aboel-Magd A. Abdel-Wahab (Assiut University, Egypt), Henri Bouas-Laurent, and Professor Dr Jean-Luc Pozzo (University of Bordeaux, France) for their continuous helpful discussions and carrying out some measurements.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Taibah University, Al-Madena Al-Mounawara, 30002, Saudi Arabia

    Saleh A. Ahmed & Shaya Y. Al-Raqa

  2. Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Saleh A. Ahmed

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  1. Saleh A. Ahmed
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  2. Shaya Y. Al-Raqa
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Correspondence to Saleh A. Ahmed.

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Ahmed, S.A., Al-Raqa, S.Y. Photochromism of dihydroindolizines. Part XV: Synthesis and photophysical properties of dihydroindolizine photoswitches bearing a conjugated aryleneethynylene tripodal linker system. Monatsh Chem 141, 357–372 (2010). https://doi.org/10.1007/s00706-010-0267-7

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