- Titel
- Pushing Up the Size Limit of Boron-doped peri-Acenes
- Untertitel
- Modular Synthesis and Characterizations
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa2-944110
- Quellenangabe
- Angewandte Chemie
Erscheinungsjahr: 2023
Jahrgang: 62
Heft: 48
E-ISSN: 1521-3773
Artikelnummer: e202312055 - Erstveröffentlichung
- 2023
- Abstract (EN)
- Heteroatom-doped peri-acenes (PAs) have recently attracted considerable attention considering their fascinating physical properties and chemical stability. However, the precise sole addition of boron atoms along the zigzag edges of PAs remains challenging, primarily due to the limited synthetic approach. Herein, we present a novel one-pot modular synthetic strategy toward unprecedented boron-doped PAs (B-PAs), including B-[4,2]PA (1 a-2), B-[4,3]PA (1 b-2) and B-[7,2]PA (1 c-3) derivatives, through efficient intramolecular electrophilic borylation. Their chemical structures are unequivocally confirmed with a combination of mass spectrometry, NMR, and single-crystal X-ray diffraction analysis. Notably, 1 b-2 exhibits an almost planar geometry, whereas 1 a-2 displays a distinctive bowl-like distortion. Furthermore, the optoelectronic properties of this series of B-PAs are thoroughly investigated by UV/Vis absorption and fluorescence spectroscopy combined with DFT calculation. Compared with their parent all-carbon analogs, the obtained B-PAs exhibit high stability, wide energy gaps, and high photoluminescence quantum yields of up to 84 %. This study reveals the exceptional ability of boron doping to finely tune the physicochemical properties of PAs, showcasing their potential applications in optoelectronics.
- Andere Ausgabe
- Link zum Artikel, der zuerst in der Zeitschrift „ Angewandte Chemie” im Verlag Wiley-VCH erschienen ist.
DOI: 10.1002/anie.202312055 - Verweis
- Ergänzendes Material ist unter folgendem Link zu finden.
Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.202312055#support-information-section - Freie Schlagwörter (EN)
- Boron Doping, Electrophilic Borylation, Peri-Acenes, Polycyclic Aromatic, Hydrocarbon
- Klassifikation (DDC)
- 540
- Verlag
- Wiley-VCH, Weinheim
- Förder- / Projektangaben
- European Commission (EC)
H2020 | SGA-RIA
Graphene Flagship Core Project 3
(GrapheneCore3)
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 - European Commission (EC)
H2020 | RIA
Multi-Electron processes for light driven electrodes and electrolytes in conversion and storage of solar energy
(LIGHT-CAP)
ID: 101017821 - Deutsche Forschungsgemeinschaft (DFG)
DFG-SNSF Joint Switzerland- German Research Project
EnhanTopo
ID: 429265950 - Version / Begutachtungsstatus
- publizierte Version / Verlagsversion
- URN Qucosa
- urn:nbn:de:bsz:14-qucosa2-944110
- Veröffentlichungsdatum Qucosa
- 04.11.2025
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis
CC BY 4.0