The gold(I)-mediated domino reaction to fused diphenyl phosphoniumfluorenes: Mechanistic Consequences for Gold-Catalyzed Hydroarylations and Application in Solar Cells
A domino sequence, involving a phosphinoauration and a gold-catalyzed 6-endo-dig cyclization step, was developed. Starting from modular and simple-to-prepare phosphadiynes, π-extended phosphoniumfluorenes were synthesized. The mechanistic proposal was supported by kinetic measurements and by the tra...
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| Main Authors: | , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
27 February 2018
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| In: |
Chemistry - a European journal
Year: 2018, Volume: 24, Issue: 31, Pages: 7882-7889 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201800460 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201800460 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201800460 
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| Author Notes: | Sebastian Arndt, Jan Borstelmann, Rebeka Eshagh Saatlo, Patrick W. Antoni, Frank Rominger, Matthias Rudolph, Qingzhi An, Yana Vaynzof, A. Stephen K. Hashmi |
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| 520 | |a A domino sequence, involving a phosphinoauration and a gold-catalyzed 6-endo-dig cyclization step, was developed. Starting from modular and simple-to-prepare phosphadiynes, π-extended phosphoniumfluorenes were synthesized. The mechanistic proposal was supported by kinetic measurements and by the trapping of key intermediates. These led to important conclusions for the gold-catalyzed hydroarylation mechanism. Cyclic voltammetry (CV) and UV/Vis spectroscopy measurements indicated interesting properties for materials science. The phosphoniumfluorene structure was tested as a hole-blocking layer in perovskite solar cells of inverted architecture. Devices with the phosphoniumfluorene exhibited an efficiency of 14.2 %, which was much higher than that of devices without (10.7 %). | ||
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