| Title: |
Benzoyl‐Xanthenoxanthenes: Versatile Chromophores for Light‐Engaging Applications |
| Authors: |
Cristian De Luca (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna); El Czar Galleposo (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna); Rúben R. Ferreira (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna); Chiara Puccinelli (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna); Herwig Peterlik (Faculty Center for Nano Structure Research, Faculty of Physics, University of Vienna); Pradip Kumar Mondal (Elettra Sincrotrone Trieste S.C.p.A.); Laurens van Dam (Department of Theoretical Chemistry, Faculty of Chemistry, University of Vienna); Johannes C. B. Dietschreit (Department of Theoretical Chemistry, Faculty of Chemistry, University of Vienna); Yoshimichi Shimomura (Department of Chemical Science and Engineering, Institute of Science Tokyo); Gen‐ichi Konishi (Department of Chemical Science and Engineering, Institute of Science Tokyo); Davide Bonifazi (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna) |
| Source: |
Angewandte Chemie International Edition ; issn:1433-7851 |
| Publisher Information: |
Wiley |
| Publication Year: |
2026 |
| Collection: |
University of Vienna: Phaidra |
| Subject Terms: |
Heteroatom doping; Light-harvesting system; NIR emitters; Polyaromatic hydrocarbons; π-Conjugated architectures |
| Description: |
In this work, we present a modular donor–acceptor strategy that produces oxidatively stable, benzoyl-fused peri-xanthenoxanthene (PXX) ribbons with near-infrared (NIR) emission and light-harvesting properties. Benzoyl fusion at the pseudo-peri positions, achieved through intramolecular Friedel–Crafts planarization, creates the first benzoyl-functionalized PXX monomers, dimers, and trimers that exhibit deep red–NIR absorption and emission without significantly raising the HOMO level. The ribbons display strong, tunable absorption and fluorescence bands, with up to 63% of emission in the NIR and an NIR fluorescence quantum yield reaching 0.36 in solution. Lewis adducts formed between boron-based Lewis acids and carbonyl acceptor sites further enhance the electron-accepting nature of the ketones, producing pure NIR emission ((Formula presented.) ≈ 0.15–0.16). Spectroelectrochemical investigations uncover reversible electrochromism and electrofluorochromism, allowing redox-gated switching and NIR absorption signatures, useful for sensing and display technologies. When embedded in a nematic liquid crystal phase, the ribbons function as cascaded Förster resonance energy transfer (FRET) antennas, achieving near-quantitative single-step energy transfer ((Formula presented.) FRET = 0.97) and highly efficient two-step transfer ((Formula presented.) FRET = 0.70), enabling directional energy funneling. Their complementary absorption broadens the excitation window to cover the entire visible spectrum, making them highly efficient panchromatic light-harvesting materials. |
| Document Type: |
article in journal/newspaper |
| File Description: |
application/pdf |
| Language: |
English |
| Relation: |
https://phaidra.univie.ac.at/o:2319549 |
| DOI: |
10.1002/anie.202523349 |
| Availability: |
https://doi.org/10.1002/anie.202523349; https://phaidra.univie.ac.at/o:2319549 |
| Rights: |
http://creativecommons.org/licenses/by/4.0/ ; © 2026 The Author(s) ; open access |
| Accession Number: |
edsbas.4930E805 |
| Database: |
BASE |