- Titel
- Modular Synthesis of Structurally Diverse Azulene-Embedded Polycyclic Aromatic Hydrocarbons by Knoevenagel-Type Condensation
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa2-943854
- Quellenangabe
- Angewandte Chemie
Erscheinungsjahr: 2023
Jahrgang: 62
Heft: 21
E-ISSN: 1521-3773
Artikelnummer: e202219091 - Erstveröffentlichung
- 2023
- Abstract (EN)
- The research interest in azulene-embedded polycyclic aromatic hydrocarbons (PAHs) has significantly increased recently, but the lack of efficient synthetic strategies impedes the investigation of their structure-property relationships and further opto-electronic applications. Here we report a modular synthetic strategy towards diverse azulene-embedded PAHs by a tandem Suzuki coupling and base-promoted Knoevenagel-type condensation with good yields and great structural versatility, including non-alternant thiophene-rich PAHs, butterfly- or Z-shaped PAHs bearing two azulene units, and the first example of a two-azulene-embedded double [5]helicene. The structural topology, aromaticity and photophysical properties were investigated by NMR, X-ray crystallography analysis and UV/Vis absorption spectroscopy assisted by DFT calculations. This strategy provides a new platform for rapidly synthesizing unexplored non-alternant PAHs or even graphene nanoribbons with multiple azulene units.
- Andere Ausgabe
- Link zum Artikel, der zuerst in der Zeitschrift „Angewandte Chemie” im Verlag Wiley-VCH erschienen ist.
DOI: 10.1002/anie.202219091 - Verweis
- Link zur englischen Ausgabe des Artikels, der zuerst in der Zeitschrift „Angewandte Chemie” bei Wiley erschienen ist.
Modulare Synthese von strukturell diversen polyzyklischen aromatischen Kohlenwasserstoffen mit eingebetteten Azulenen durch Knoevenagelartige Kondensation - Freie Schlagwörter (EN)
- Aromaticity, Azulene, Helicenes, Polycyclic Aromatic Hydrocarbons, Structure Elucidation
- Klassifikation (DDC)
- 540
- Verlag
- Wiley-VCH, Weinheim
- Förder- / Projektangaben
- European Commission (EC)
H2020 | SGA-RIA
Flagship Core Project 3
(GrapheneCore3 Graphene)
ID: 881603 - European Commission (EC)
H2020 | ERC | ERC-COG
Development of Thiophene Based Conjugated Polymers in Two Dimensions
(T2DCP)
ID: 819698 - European Commission (EC)
H2020 | MSCA-ITN-ETN
Bottom-Up generation of atomicalLy precise syntheTIc 2D MATerials for high performance in energy and Electronic applications – A multi-site innovative training action
(ULTIMATE)
ID: 813036 - Center for Advancing Electronics Dresden (cfaed)
H2020-EU.1.2.2.—FET
ID: 101017821 - Deutsche Forschungsgemeinschaft (DFG)
ID: 429265950 - Version / Begutachtungsstatus
- publizierte Version / Verlagsversion
- URN Qucosa
- urn:nbn:de:bsz:14-qucosa2-943854
- Veröffentlichungsdatum Qucosa
- 04.11.2025
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis
CC BY 4.0