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  The Fluorenyl Cation

Costa, P., Trosien, I., Fernandez-Oliva, M., Sanchez-Garcia, E., & Sander, W. (2015). The Fluorenyl Cation. Angewandte Chemie International Edition, 54(9), 2656-2660. doi:10.1002/anie.201411234.

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ange_201411234_sm_miscellaneous_information.pdf (Supplementary material), 4MB
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ange_201411234_sm_miscellaneous_information.pdf
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Supporting Information
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Copyright Date:
2015
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Wiley-VCH, 69451 Weinheim, Germany
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 Creators:
Costa, Paolo1, Author
Trosien, Iris1, Author
Fernandez-Oliva, Miguel2, Author           
Sanchez-Garcia, Elsa2, Author           
Sander, Wolfram1, Author
Affiliations:
1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, 44780 Bochum (Germany), ou_persistent22              
2Research Group Sánchez-García, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1950289              

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Free keywords: antiaromaticity; carbenium ions; IR spectroscopy; matrix isolation; QM/MM calculations
 Abstract: The fluorenyl cation is a textbook example for a 4π antiaromatic cation. However, contrasting results have been published on how the annelated benzene rings compensate the destabilizing effect of the 4π antiaromatic five-membered ring in its core. Whereas previous attempts to synthesize this cation in superacidic media resulted in undefined polymeric material only, we herein report that it can be generated and isolated in amorphous water ice at temperatures below 30 K by photolysis of diazofluorene. Under these conditions, the fluorenylidene is protonated by water to give the fluorenyl cation, which could be characterized spectroscopically. Its absorption in the visible-light range matches that previously obtained by ultrafast absorption spectroscopy, and furthermore, its IR spectrum could be recorded. The IR bands in amorphous ice very nicely match predictions from DFT and DFT/MM calculations, suggesting the absence of strong interactions between the cation and surrounding water molecules.

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Language(s): eng - English
 Dates: 2014-11-092015-02-052015-02-23
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201411234
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 54 (9) Sequence Number: - Start / End Page: 2656 - 2660 Identifier: ISSN: 1521-3773
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833