biostudies-literatureDelouche TANRe202205548https://www.ebi.ac.uk/biostudies/studies/S-EPMC9400969biostudies-literatureUnknown61(31)We report the straightforward one-pot synthesis of novel 5- or 6-membered P-heterocycles featuring an internal ylidic bond: P-containing acenaphthylenes and phenanthrenes. The stability of the compounds tolerates post-functionalization through direct arylation to introduce electron-rich/poor substituents and the synthetic strategy is also compatible with the preparation of more elaborate polyaromatic scaffolds such as acenes and helicenes. Using a joint experimental (X-ray analysis, optical and redox properties) and theoretical approach, we perform a full structure-property relationships study on these new platforms. In particular, we show that molecular engineering allows not only tuning their absorption/emission across the entire visible range but also endowing them with chiroptical or non-linear optical properties, making them valuable dyes for a large panel of photonic or opto-electronic applications.Angewandte Chemie (International ed. in English)Straightforward Access to Multifunctional π-Conjugated P-Heterocycles Featuring an Internal Ylidic Bond.PMC9400969ANR-16-CE05-0003-01Taupier GVanthuyne NHissler MRoisnel TMolard YCordier MBouit PADelouche TCaytan EJacquemin DLe Guennic BfalseStraightforward Access to Multifunctional π-Conjugated P-Heterocycles Featuring an Internal Ylidic Bond.We report the straightforward one-pot synthesis of novel 5- or 6-membered P-heterocycles featuring an internal ylidic bond: P-containing acenaphthylenes and phenanthrenes. The stability of the compounds tolerates post-functionalization through direct arylation to introduce electron-rich/poor substituents and the synthetic strategy is also compatible with the preparation of more elaborate polyaromatic scaffolds such as acenes and helicenes. Using a joint experimental (X-ray analysis, optical and redox properties) and theoretical approach, we perform a full structure-property relationships study on these new platforms. In particular, we show that molecular engineering allows not only tuning their absorption/emission across the entire visible range but also endowing them with chiroptical or non-linear optical properties, making them valuable dyes for a large panel of photonic or opto-electronic applications.2022-01-01T00:00:00Z2022 Aug2025-06-01T01:32:28.734Z2025-06-01T01:32:28.734ZS-EPMC94009693565768510.1002/anie.202205548