AIE‐Active Difluoroboron Complexes with N,O‐Bidentate Ligands: Rapid Construction by Copper‐Catalyzed C−H Activation
Open Access
- 26 July 2021
- journal article
- research article
- Published by Wiley in Advanced Science
- Vol. 8 (18) , 2101814
Abstract
The development of organic materials with high solid‐state luminescence efficiency is highly desirable because of their fundamental importance and applicability in optoelectronics. Herein, a rapid construction of novel BF2 complexes with N,O‐bidentate ligands by using Cu(BF4)2•6H2O as a catalyst and BF2 source is disclosed, which avoids the need for pre‐composing the N,O‐bidentate ligands and features a broad substrate scope and a high tolerance level for sensitive functional groups. Moreover, molecular oxygen is employed as the terminal oxidant in this transformation. A library of 36 compounds as a new class of BF2 complexes with remarkable photophysical properties is delivered in good to excellent yields, showing a substituent‐dependency on the photophysical properties, derived from the π–π* character of the photoexcited state. In addition, aggregation‐induced emission (AIE) is observed and quantified for the brightest exemplars. The excited state properties are fully investigated in solids and in THF/H2O mixtures. Hence, a new series of photofunctional materials with variable photophysical properties is reported, with potential applications for sensing, bioimaging, and optoelectronics.Keywords
Funding Information
- Deutsche Forschungsgemeinschaft (SPP2102, SFB 858, INST 211/915‐1)
- Ministerium für Innovation, Wissenschaft und Forschung des Landes Nordrhein-Westfalen (INST 211/915‐1 FUGG)
This publication has 96 references indexed in Scilit:
- Azadipyrromethenes: from traditional dye chemistry to leading edge applicationsChemical Society Reviews, 2016
- BODIPY-based probes for the fluorescence imaging of biomolecules in living cellsChemical Society Reviews, 2015
- Structural modification strategies for the rational design of red/NIR region BODIPYsChemical Society Reviews, 2014
- Fluorescent indicators based on BODIPYChemical Society Reviews, 2011
- The Chemistry of Fluorescent Bodipy Dyes: Versatility UnsurpassedAngewandte Chemie International Edition, 2008
- BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic PropertiesChemical Reviews, 2007
- Excimers and Exciplexes of Conjugated PolymersScience, 1994
- Difluorboryl‐Komplexe von Di‐ und TripyrrylmethenenEuropean Journal of Organic Chemistry, 1968
- Concentration Quenching of Fluorescence in Chlorophyll SolutionsNature, 1948
- FLUORESCENCE OF ORGANIC MOLECULES*Nature, 1943