Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
Zitieren Sie bitte immer diese URN: urn:nbn:de:bvb:20-opus-225775
- Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All‐ortho‐fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (Φ\(_{fl}\)) of 18–24 % in solution, green or yellow solid‐state emission (Φ\(_{fl}\) up to 23 %), and strong chiroptical response with large dissymmetryTwo types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All‐ortho‐fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (Φ\(_{fl}\)) of 18–24 % in solution, green or yellow solid‐state emission (Φ\(_{fl}\) up to 23 %), and strong chiroptical response with large dissymmetry factors of up to 1.12×10\(^{-2}\). Azabora[9]helicenes consisting of angularly and linearly fused rings are blue emitters exhibiting Φ\(_{fl}\) of up to 47 % in CH\(_{2}\)Cl\(_{2}\) and 25 % in the solid state. As revealed by the DFT calculations, their P–M interconversion pathway is more complex than that of H1. Single‐crystal X‐ray analysis shows clear differences in the packing arrangement of methyl and phenyl derivatives. These molecules are proposed as primary structures of extended helices.…
Autor(en): | Julian Full, Santosh P. Panchal, Julian Götz, Ana‐Maria Krause, Agnieszka Nowak‐Król |
---|---|
URN: | urn:nbn:de:bvb:20-opus-225775 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Angewandte Chemie International Edition |
Erscheinungsjahr: | 2021 |
Band / Jahrgang: | 60 |
Heft / Ausgabe: | 8 |
Erste Seite: | 4350 |
Letzte Seite: | 4357 |
Originalveröffentlichung / Quelle: | Angewandte Chemie International Edition 2021, 60(8):4350–4357. DOI: 10.1002/anie.202014138 |
DOI: | https://doi.org/10.1002/anie.202014138 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Freie Schlagwort(e): | chirality; circular dichroism; fluorescence; helicene; organoboron |
Datum der Freischaltung: | 15.10.2021 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |