Zitieren Sie bitte immer diesen URN: urn:nbn:de:kobv:b43-642400
Ester‐Aroyl‐S,N‐Ketene Acetals with Solid‐State Luminescence: AIEgens from Sequential Three‐Component Desymmetrization
- AbstractDi(hetero)aroyl dichlorides are desymmetrized upon sequential reaction with alcohols and 2‐methyl N‐benzyl thiazolium salts within the course of a one‐pot three‐component reaction yielding ester‐substituted aroyl‐S,N‐ketene acetals under mild conditions in good yields. A prerequisite for the concise one‐pot process is the different nucleophilicity of the alcohols and in situ generated S,N‐ketene acetals. The resulting compounds are merocyanines with dominant charge‐transfer absorption bands which are fluorescent in the solid state, but not in solution. In water/ethanol solvent mixtures of increasing water content, the water‐insoluble dyes display typical aggregation‐induced emission (AIE) characteristics. The water fraction inducing AIE as well as the emission color, and fluorescence quantum yield (Φf) of the aggregated dyes can be controlled by the alcohol part of the ester moiety. Encapsulation into polystyrene nanoparticles can lead to a considerable increase of theAbstractDi(hetero)aroyl dichlorides are desymmetrized upon sequential reaction with alcohols and 2‐methyl N‐benzyl thiazolium salts within the course of a one‐pot three‐component reaction yielding ester‐substituted aroyl‐S,N‐ketene acetals under mild conditions in good yields. A prerequisite for the concise one‐pot process is the different nucleophilicity of the alcohols and in situ generated S,N‐ketene acetals. The resulting compounds are merocyanines with dominant charge‐transfer absorption bands which are fluorescent in the solid state, but not in solution. In water/ethanol solvent mixtures of increasing water content, the water‐insoluble dyes display typical aggregation‐induced emission (AIE) characteristics. The water fraction inducing AIE as well as the emission color, and fluorescence quantum yield (Φf) of the aggregated dyes can be controlled by the alcohol part of the ester moiety. Encapsulation into polystyrene nanoparticles can lead to a considerable increase of the fluorescence quantum yield Φf to 30% as shown for a representatively chosen dye revealing the highest Φf of 11% within the dye series in the water/ethanol mixtures and enabling the usage of these dyes as fluorescent reporters in aqueous environments.…


| Autor*innen: | Yannic Hartmann, Abdelouahad El Abbassi, Bernhard Mayer, Ute Resch-GengerORCiD, Thomas J. J. MüllerORCiD |
|---|---|
| Dokumenttyp: | Zeitschriftenartikel |
| Veröffentlichungsform: | Verlagsliteratur |
| Sprache: | Englisch |
| Titel des übergeordneten Werkes (Englisch): | Chemistry – A European Journal |
| Jahr der Erstveröffentlichung: | 2025 |
| Organisationseinheit der BAM: | 1 Analytische Chemie; Referenzmaterialien |
| 1 Analytische Chemie; Referenzmaterialien / 1.2 Biophotonik | |
| Veröffentlichende Institution: | Bundesanstalt für Materialforschung und -prüfung (BAM) |
| Verlag: | Wiley-VCH |
| Verlagsort: | Weinheim |
| Aufsatznummer: | e02071 |
| Erste Seite: | 1 |
| Letzte Seite: | 10 |
| DDC-Klassifikation: | Naturwissenschaften und Mathematik / Chemie / Analytische Chemie |
| Technik, Medizin, angewandte Wissenschaften / Ingenieurwissenschaften / Ingenieurwissenschaften und zugeordnete Tätigkeiten | |
| Freie Schlagwörter: | Aggregation; Characterization; Dye; Fluorescence; Lifetime; Mechanism; Nano; Particle; Photophysics; Polarity; Probe; Quantum yield; Sensor; Signal enhancement |
| Themenfelder/Aktivitätsfelder der BAM: | Chemie und Prozesstechnik |
| Chemie und Prozesstechnik / Chemische Charakterisierung und Spurenanalytik | |
| Umwelt | |
| DOI: | 10.1002/chem.202502071 |
| URN: | urn:nbn:de:kobv:b43-642400 |
| ISSN: | 0947-6539 |
| Verfügbarkeit des Dokuments: | Datei für die Öffentlichkeit verfügbar ("Open Access") |
| Lizenz (Deutsch): | Creative Commons - CC BY - Namensnennung 4.0 International |
| Datum der Freischaltung: | 01.10.2025 |
| Referierte Publikation: | Ja |
| Datum der Eintragung als referierte Publikation: | 01.10.2025 |
| Schriftenreihen ohne Nummerierung: | Wissenschaftliche Artikel der BAM |


