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- W4387563587 abstract "The first ever case of a tandem intramolecular hydroarylation of alkynes accompanied by a 1,2-aryl shift is described. Harnessing the unique electron-rich character of 1,4-dihydropyrrolo[3,2-b]pyrrole scaffolds, we have demonstrated that the hydroarylation of alkynes proceeds at the already occupied positions 2 and 5 leading to a 1,2-aryl shift. Remarkably, the reaction proceeds only in the presence of cationic gold catalyst, and it leads to heretofore unknown π-expanded, centrosymmetric pyrrolo[3,2-b]pyrroles. The utility is verified in the preparation of 13 products that bear six conjugated rings. The observed compatibility with various functional groups allows for increased tunability with regard to the photophysical properties as well as providing sites for further functionalization. Our computational studies additionally suggest that the formation of the six-membered rings accompanied with a 1,2-aryl shift is a highly exoergic process, whereas the formation of products containing 7-membered rings is endoergic, rationalizing the observed reaction course. Steady-state UV/visible spectroscopy revealed that upon photoexcitation, the prepared S-shaped N-doped nanographenes undergo mostly radiative relaxation leading to large fluorescence quantum yields. Their optical properties were rationalized through TD-DFT calculations. We anticipate that this chemistry will empower the creation of new materials with various functionalities." @default.
- W4387563587 created "2023-10-13" @default.
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- W4387563587 date "2023-10-12" @default.
- W4387563587 modified "2023-10-13" @default.
- W4387563587 title "Unprecedented 1,2‐Aryl Shift Accompanying Double Alkyne Benzannulation" @default.
- W4387563587 doi "https://doi.org/10.1002/anie.202311123" @default.
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- W4387563587 hasPublicationYear "2023" @default.
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