Synthesis and Properties of BODIPY Appended Tetraphenylethylene Scaffolds as Photoactive Arrays
Item Type:Journal Article
Citation:Sample, Harry C., Emandi, Ganapathi, Twamley, Brendan, Grover, Nitika, Khurana, Bhavya, Sol, Vincent, Senge, Mathias, 'Synthesis and Properties of BODIPY Appended Tetraphenylethylene Scaffolds as Photoactive Arrays', European Journal of Organic Chemistry, 2021, 29
Tetraphenylethylene (TPE) and its derivatives exhibit excellent aggregation-induced emission (AIE) properties. The TPE unit is easily accessible, and many functional groups can be introduced in a facile manner to yield effective luminescent materials in both solution and the solid-state. It is because of this, several TPE-based compounds have been developed and applied in many areas, such as OLEDs and chemical sensors. Boron dipyrromethenes (BODIPYs) are a class of pyrrolic fluorophore of great interest with myriad application in both material science and biomedical applications. Through the combination of Pd-catalyzed cross-coupling reactions and traditional dipyrromethene chemistry, we present the syntheses of novel tetra-BODIPY-appended TPE derivatives with different distances between the TPE and BODIPY cores. The TPE-BODIPY arrays 6 and 9 show vastly differing AIE properties in THF/H2O systems, with 9 exhibiting dual-AIE, along with both conjugates being found to produce singlet oxygen (1O2). We presume the synthesized BODIPY-appended TPE scaffolds to be utilized for potential applications in the fields of light-emitting systems and theranostics.
Science Foundation Ireland
Author: Senge, Mathias; Khurana, Bhavya; Grover, Nitika; Twamley, Brendan; Emandi, Ganapathi; Sample, Harry C.
Type of material:Journal Article
Series/Report no:European Journal of Organic Chemistry;
Availability:Full text available