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Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties

Chenchen Li, Haiyang Huang, Longgen Sun, Mingqing Huang, Haixin Ding, Jiang Bai, Banpeng Cao, Qiang Xiao

2022Angewandte Chemie International Edition14 citationsDOI

Abstract

Rigidly planar polycyclic phosphacycles featuring an internal dioxaphosphorane are promising photofunctional materials. However, the lack of efficient synthetic methods resulted in limited structural diversities which significantly hampered extensive study. Herein, we report a straightforward three-component synthesis of novel dioxaphosphorane-fused diphosphacycles with distinctive photophysical properties. Control experiments and theory calculations were performed to account for a plausible reaction mechanism. We also systematically investigated the structure-property relationships of these unprecedented platforms by combining experiments (X-ray analysis, optical and redox properties) and theoretical computations. Based on their unique structure and properties, a novel fluorescent switch for pH sensing was revealed by a dynamic ring-opening/ring-closing process.

Topics & Concepts

FluorescencePlanarComponent (thermodynamics)Ring (chemistry)Closing (real estate)Biological systemMaterials scienceNanotechnologyCombinatorial chemistryRedoxChemistryComputer scienceOpticsPhysicsOrganic chemistryPolitical scienceBiologyLawMetallurgyThermodynamicsComputer graphics (images)Synthesis and characterization of novel inorganic/organometallic compoundsOrganoboron and organosilicon chemistrySynthetic Organic Chemistry Methods
Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties | Litcius