Synthesis and Properties of BODIPY Appended Tetraphenylethylene Scaffolds as Photoactive Arrays
Open Access
- 7 July 2021
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2021 (29), 4136-4143
- https://doi.org/10.1002/ejoc.202100629
Abstract
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 dipyrromethanes (BODIPYs) are a class of pyrrolic fluorophore of interest with myriad application in both material science and biomedicine. Through the combination of Pd-catalyzed cross-coupling reactions and traditional dipyrromethane chemistry, we present the syntheses of novel tetra-BODIPY-appended TPE derivatives with different ‘arm’ lengths. The TPE-BODIPY arrays 6 and 9 show vastly differing AIE properties in THF/H 2 O systems, with 9 exhibiting dual-AIE, along with both conjugates being found to produce singlet oxygen ( 1 O 2 ). We presume the synthesized BODIPY-appended TPE scaffolds to be utilized for potential applications in the fields of light harvesting systems and delivery of photosensitizers and for the construction of porous materials.Keywords
Funding Information
- Science Foundation Ireland (IvP 13/IA/1894)
- Irish Research Council (GOIPD/2017/1395)
This publication has 58 references indexed in Scilit:
- Ethynyl-Capped Hyperbranched Conjugated Polytriazole: Click Polymerization, Clickable Modification, and Aggregation-Enhanced EmissionMacromolecules, 2012
- OLEX2: a complete structure solution, refinement and analysis programJournal of Applied Crystallography, 2009
- A short history of SHELXActa Crystallographica Section A Foundations of Crystallography, 2007
- FRET-Nachweis geometrisch präzise definierter Expansions-Kontraktions-Bewegungen im Multinanometerbereich eines Resorcin[4]aren-Cavitand-basierten SchaltersAngewandte Chemie, 2005
- Synthesis of Highly Conjugated Two-Dimensional Molecular Scaffolds via Pd-Catalyzed Reactions on a Tetraphenylethylene CoreSynlett, 2004
- Singlet oxygen formation and photostability of meso-tetraarylporphyrin derivatives and their copper complexesJournal of Photochemistry and Photobiology A: Chemistry, 2001
- Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsiloleChemical Communications, 2001
- Reduction of Acetylated Tetraphenylethylenes: Electrochemical Behavior and Stability of the Related Reduced AnionsThe Journal of Organic Chemistry, 1996
- The Excited State Potential Energy Surface for the Photoisomerization of Tetraphenylethylene: A Fluorescence and Picosecond Optical Calorimetry InvestigationJournal of the American Chemical Society, 1994
- Zur Konstitution des TriphenylmethylsEuropean Journal of Inorganic Chemistry, 1907