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Article Dans Une Revue Journal of Organic Chemistry Année : 2022

Planar Chiral Analogues of PRODAN Based on a [2.2]Paracyclophane Scaffold: Synthesis and Photophysical Studies

Résumé

We describe the synthesis and photophysical characterization of differently substituted planar chiral analogues of PRODAN based on a [2.2]paracyclophane scaffold. This experimental and theoretical study highlights that the (chir)optical properties of the new "phane" compounds, which incorporate an electron-withdrawing propionyl moiety and an electron-donating dimethylamino group at their para or pseudo Para positions, strongly depend on their substitution patterns. In particular, for this series of molecules, a more pronounced solvatochromism and clear chiroptical behaviors are observed when the two substituents are placed on the two rings of the pCp core in a non-"co-planar" arrangement (pseudo Para derivative). This observation may help design new pCp-based luminophores with finely tuned photophysical properties.
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Dates et versions

hal-03512519 , version 1 (07-02-2022)

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Simon Felder, Marie-Leonie Delcourt, Manon H. E. Bousquet, Denis Jacquemin, Rafael Rodriguez, et al.. Planar Chiral Analogues of PRODAN Based on a [2.2]Paracyclophane Scaffold: Synthesis and Photophysical Studies. Journal of Organic Chemistry, 2022, 87 (1), pp.147-158. ⟨10.1021/acs.joc.1c02071⟩. ⟨hal-03512519⟩
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