Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c10865
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Funding
- Julius-Maximilians-Universitat Wurzburg
- Alexander von Humboldt Foundation
- German Research Foundation (DFG) [1459/1-1]
- Hector Fellow Academy (HFA)
- HFA
- CNPq
- FAPERJ
- CAPES
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The intrinsic relationship between helicenes and circulenes is of fundamental interest and importance in molecular engineering. In this study, electrophilic borylation of phenanthroline-derived aza[5]helicenes was performed, resulting in the incorporation of a boryl unit into two termini of helicenes to form quasi-[7]circulenes. Their bowl-shaped structures were determined by X-ray diffraction. UV-vis absorption and fluorescence spectroscopy, electrochemical measurements, and DFT calculations provided insights into their electronic properties. Variable-temperature NMR studies and DFT calculations revealed the bowl-to-bowl inversion at room temperature and bowl-to-helix equilibria at elevated temperature, highlighting the important role of B <- N bond strength in tuning their dynamic properties.
The intrinsic relationship between helicenes and circulenes is of fundamental interest and importance in molecular engineering. Herein, electrophilic borylation of phenanthroline-derived aza[5]helicenes is presented, resulting in the incorporation of a boryl unit into two termini of helicenes to afford quasi-[7]circulenes. Their bowl-shaped structures were determined by X-ray diffraction. UV-vis absorption and fluorescence spectroscopy, as well as electrochemical measurements and DFT calculations, gave insight into their electronic properties. Variable-temperature NMR studies and DFT calculations revealed bowl-to-bowl inversion at room temperature and bowl-to-helix equilibria at elevated temperature, highlighting the important role of B <- N bond strength in tuning their dynamic properties.
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