Enhanced Optical Properties of Azaborole Helicenes by Lateral and Helical Extension
Please always quote using this URN: urn:nbn:de:bvb:20-opus-293671
- The synthesis and characterization of laterally extended azabora[5]‐, ‐[6]‐ and ‐[7]helicenes, assembled from N‐heteroaromatic and dibenzo[g,p]chrysene building blocks is described. Formally, the π‐conjugated systems of the pristine azaborole helicenes were enlarged with a phenanthrene unit leading to compounds with large Stokes shifts, significantly enhanced luminescence quantum yields (Φ) and dissymmetry factors (g\(_{lum}\)). The beneficial effect on optical properties was also observed for helical elongation. The combined contributions ofThe synthesis and characterization of laterally extended azabora[5]‐, ‐[6]‐ and ‐[7]helicenes, assembled from N‐heteroaromatic and dibenzo[g,p]chrysene building blocks is described. Formally, the π‐conjugated systems of the pristine azaborole helicenes were enlarged with a phenanthrene unit leading to compounds with large Stokes shifts, significantly enhanced luminescence quantum yields (Φ) and dissymmetry factors (g\(_{lum}\)). The beneficial effect on optical properties was also observed for helical elongation. The combined contributions of lateral and helical extensions resulted in a compound showing green emission with Φ of 0.31 and |g\(_{lum}\)| of 2.2×10\(^{−3}\), highest within the series of π‐extended azaborahelicenes and superior to emission intensity and chiroptical response of its non‐extended congener. This study shows that helical and lateral extensions of π‐conjugated systems are viable strategies to improve features of azaborole helicenes. In addition, single crystal X‐ray analysis of configurationally stable [6]‐ and ‐[7]helicenes was used to provide insight into their packing arrangements.…
Author: | Felix Full, Quentin Wölflick, Krzysztof Radacki, Holger BraunschweigORCiD, Agnieszka Nowak‐Król |
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URN: | urn:nbn:de:bvb:20-opus-293671 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Fakultät für Chemie und Pharmazie / Institut für Organische Chemie | |
Language: | English |
Parent Title (English): | Chemistry – A European Journal |
Year of Completion: | 2022 |
Volume: | 28 |
Issue: | 62 |
Article Number: | e202202280 |
Source: | Chemistry – A European Journal 2022, 28(62):e202202280. DOI: 10.1002/chem.202202280 |
DOI: | https://doi.org/10.1002/chem.202202280 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Tag: | azaborole; circularly polarized luminescence; fluorescence; helicene; π-extension |
Release Date: | 2023/06/19 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |