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Near-Infrared Quadrupolar Chromophores Combining Three-Coordinate Boron-Based Superdonor and Superacceptor Units
Please always quote using this URN: urn:nbn:de:bvb:20-opus-180391
- In this work, two new quadrupolar A-π-D-π-A chromophores have been prepared featuring a strongly electron- donating diborene core and strongly electron-accepting dimesitylboryl F(BMes2) and bis(2,4,6-tris(trifluoromethyl)phenyl)boryl (BMes2) end groups. Analysis of the compounds by NMR spectroscopy, X-ray crystallography, cyclic voltammetry and UV-vis-NIR absorption and emission spectroscopy indicated that the compounds possess extended conjugated π-systems spanning their B4C8 cores. The combination of exceptionally potent π-donor (diborene)In this work, two new quadrupolar A-π-D-π-A chromophores have been prepared featuring a strongly electron- donating diborene core and strongly electron-accepting dimesitylboryl F(BMes2) and bis(2,4,6-tris(trifluoromethyl)phenyl)boryl (BMes2) end groups. Analysis of the compounds by NMR spectroscopy, X-ray crystallography, cyclic voltammetry and UV-vis-NIR absorption and emission spectroscopy indicated that the compounds possess extended conjugated π-systems spanning their B4C8 cores. The combination of exceptionally potent π-donor (diborene) and π- acceptor (diarylboryl) groups, both based on trigonal boron, leads to very small HOMO-LUMO gaps, resulting in strong absorption in the near-IR region with maxima in THF at 840 and 1092 nm, respectively, and very high extinction coefficients of ca. 120,000 M-1cm-1. Both molecules also display weak near-IR fluorescence with small Stokes shifts.…
Author: | Tom E. Stennett, Philipp Bissinger, Stefanie Griesbeck, Stefan Ullrich, Ivo Krummenacher, Michael Auth, Andreas Sperlich, Matthias Stolte, Krzysztof Radacki, Chang-Jiang Yao, Frank WürthnerORCiDGND, Andreas Steffen, Todd B. Marder, Holger BraunschweigORCiD |
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URN: | urn:nbn:de:bvb:20-opus-180391 |
Document Type: | Preprint |
Faculties: | Fakultät für Physik und Astronomie / Physikalisches Institut |
Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie | |
Fakultät für Chemie und Pharmazie / Institut für Organische Chemie | |
Language: | English |
Parent Title (English): | Angewandte Chemie, International Edition |
Year of Completion: | 2019 |
Source: | Angewandte Chemie, International Edition 2019, 58, 19, 6449-6454. doi:10.1002/anie.201900889 |
DOI: | https://doi.org/10.1002/anie.201900889 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Tag: | boron; conjugation; low-valent compounds; near-IR chromophores; synthesis |
Release Date: | 2019/05/14 |
EU-Project number / Contract (GA) number: | 669054 |
OpenAIRE: | OpenAIRE |
Note: | This is the pre-peer reviewed version of the following article: T. E. Stennett, P. Bissinger, S. Griesbeck, S. Ullrich, I. Krummenacher, M. Auth, A. Sperlich, M. Stolte, K. Radacki, C.-J. Yao, F. Wuerthner, A. Steffen, T. B. Marder, H. Braunschweig, Angew. Chem. Int. Ed. 2019, 58, 6449. , which has been published in final form at https://doi.org/10.1002/anie.201900889. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
Licence (German): | Deutsches Urheberrecht |