Easy access to polyaromatics featuring stable internal ylidic bond: toward electronic/photonic applications

A straightforward one-pot synthesis of novel P-heterocycles featuring an internal ylidic bond is reported. These unprecedented pi-systems appears as valuable dyes for photonic and opto-electronic applications.
Easy access to polyaromatics featuring stable internal ylidic bond: toward electronic/photonic applications

In the field of molecular materials based on phosphorus-containing π-systems, little attention was devoted to phosphacycles featuring an internal P-ylide (negative carbon atom adjacent to a positive P atom). Hence, this bond was supposed to be too reactive. Actually, organic chemists use this reactivity since decades to create C-C bond with the Wittig reaction. Chemists from the Rennes Institute of Chemical Sciences recently developed a rapid one-pot synthesis of 5 or 6-membered P-heterocycles featuring an internal ylidic bond, which are fully air and moisture stable, thanks to judicious substitution. Such stability offers the possibility to perform post-functionalization using P-catalysed direct arylation to introduce various chemical functions. The synthetic approach is fully compatible with the synthesis of larger polyaromatic systems such hetero-acenes and hetero-helicenes. Finally, in collaboration with colleagues from ScanMat (UAR 2001), CEISAM Lab (UMR 6230) and iSm2 (UMR7313), they show that these chemical modifications allow efficiently tuning their spectroscopic/redox properties but also endowing them with non-linear optical properties (two-photon absorption) or chiroptical properties, making them attractive dyes for opto-electronic or photonic applications.

 

Reference

Straightforward Access to Multifunctional p-Conjugated P-Heterocycles Featuring an Internal Ylidic Bond
T. Delouche, E. Caytan, M. Cordier, T. Roisnel, G. Taupier, Y. Molard, N. Vanthuyne, B. Le Guennic, M. Hissler, D. Jacquemin, P.-A. Bouit
Angew. Chem. Int. Ed, 2022, 10.1002/anie.202205548 - https://doi.org/10.1002/anie.202205548

Contact

Pierre-Antoine Bouit, Univ Rennes, CNRS, ISCR-UMR 6226, F-35000 Rennes, France
pierre-antoine [dot] bouitatuniv-rennes1 [dot] fr

 

Published June 29, 2022