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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: Arndt, Sebastian (Author) , Antoni, Patrick W. (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , An, Qingzhi (Author) , Vaynzof, Yana (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 27 February 2018
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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Summary: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 %).
Item Description:Gesehen am 29.08.2018
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201800460

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