Highly Conjugated Bis(benzo[b]phosphole)‐P‐oxides: Synthesis and Electrochemical, Optical, and Computational Studies. Issue 4 (30th December 2022)

• Record Type: Journal Article
• Authors: D'Imperio, Nicolas; Pelliccioli, Valentina; Grecchi, Sara; Bossi, Alberto; Vasile, Francesca; Cauteruccio, Silvia; Arkhypchuk, Anna I.; Kumar Gupta, Arvind; Orthaber, Andreas; Ott, Sascha; Licandro, Emanuela
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 4(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-30
• Subjects: benzophospholes -- cyclic voltammetry -- diastereomers -- fluorescence -- π-conjugation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201209
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The first examples of a π‐conjugated benzo[ b ]phosphole P ‐oxide in which two phosphole P ‐oxide units are connected by a carbon‐carbon double bond are described. The molecules are synthesized as E isomers with respect to the carbon‐carbon double bond and exist as stable cis and trans isomers (chiral and meso one respectively) relatively to the two stereogenic P atoms. The optical and electrochemical properties of both isomers have been investigated by experiment and computations. Abstract : The synthesis of the two diastereoisomers cis ‐( E )‐1 and trans ‐( E )‐1 (the chiral and meso one respectively) containing two stereogenic P atoms has been accomplished in three different ways. This highly conjugated bis‐(benzo[ b ]phosphole) P ‐oxide has been characterized by means of electrochemical and photophysical studies and the relative configuration of the two diastereoisomers assigned through CV and NMR studies.