Tetraphenylethene 9,10‐Diphenylanthracene Derivatives – Synthesis and Photophysical Properties

• Published in: ChemPlusChem (Weinheim, Germany) Vol. 84; no. 6; pp. 746 - 753
• Main Authors: Gao, Can, Seow, Jia Yi, Zhang, Bolong, Hall, Christopher R., Tilley, Andrew J., White, Jonathan M., Smith, Trevor A., Wong, Wallace W. H.
• Format: Journal Article
• Language: English
• Published: Germany 01.06.2019
• Subjects: aggregation induced emission; anthracene; photoluminescence; photon upconversion; tetraphenylethene; anthracene; tetraphenylethene; photoluminescence; photon upconversion; aggregation induced emission
• ISSN: 2192-6506; 2192-6506
• DOI: 10.1002/cplu.201900100

A series of tetraphenylethene 9,10‐diphenylanthracene (TPE‐DPA) derivatives have been synthesized, and their photophysical properties studied. Photoluminescence measurements in PMMA, neat films and nanoparticle dispersions reveal that different aggregation states are formed, which leads to different photophysical behavior. The triplet excited state properties were studied using Pt(II) octaethylporphyrin (PtOEP) as triplet sensitizer. Upconverted emission from the DPA moiety is observed in nanoparticle dispersions of each derivative. A higher upconverted emission intensity is observed in aerated (compared to deaerated) solutions of the derivatives following irradiation, which is attributed to oxidation of the TPE moiety. These results provide valuable insight for the design of AIE luminogens for triplet‐triplet annihilation upconversion (TTA‐UC). Bright idea: Tetraphenylethene 9,10‐diphenylanthracenes (TPE‐DPAs) were synthesized and characterized. The TPE‐DPAs displayed aggregation induced emission behavior and were shown to work as emitters in nanoparticle triplet‐triplet annihilation upconversion systems with platinum porphyrin as triplet sensitizer.