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Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties

Abstract : Ynamides are useful and versatile building blocks in organic synthesis, from which 1,1,4,4-tetracyanobutadienes (TCBD) can be prepared for application in molecular electronics. However, their insertion onto multi-functional molecular scaffold remains a synthetic challenge. In this work, we report the two-steps synthesis in good isolated yield (64% overall, 89 degrees o stepwise) of a tetraphenylethylene (TPE) bearing four ynamides, and its further one-step conversion into the tetra-TCBD derivative through a [2 + 2] cycloaddition-retroelectrocyclization sequence. The concomitant formation of the four ynamides required a specific optimisation of the reaction conditions. Although a poor fluorescent emitter in solution, the tetra-TCBD compound displayed near-infrared luminescence in the solid state, which is an attractive optoelectronic feature when considering future applications in molecular electronic devices.
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https://hal.archives-ouvertes.fr/hal-03657696
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Tuesday, July 19, 2022 - 2:50:02 PM
Last modification on : Friday, August 5, 2022 - 10:37:42 AM

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Distributed under a Creative Commons Attribution - NonCommercial 4.0 International License

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Clotilde Philippe, Maëva Coste, Yann Bretonnière, Loïc Lemiègre, Sebastien Ulrich,, et al.. Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2022, 2022 (21), pp.e202200049. ⟨10.1002/ejoc.202200049⟩. ⟨hal-03657696⟩

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