JACS Au· 2026Q1
Complete Isocyanide Triple Bond Scission by a Silylene Yields an Optoelectronic 1,3-Disilacyclobutene
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- Q1SCImago
- 2026year
Short summary
A hypersilyl-stabilized silylene completely cleaves the C≡N triple bond in aryl isocyanides, forming novel cyclic silenes, one of which functions as a hole-injection layer in a light-emitting diode.
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Key points
- A silylene achieved complete cleavage of the isocyanide C≡N triple bond, setting a new benchmark for main-group element small-molecule activation.
- Aryl isocyanides undergo rearrangement and C≡N/Si–Si bond scission to form novel cyclic silenes (2 and 3).
- Cyclohexyl isocyanide, however, leads to a stable insertion product (4) without oxidizing the silicon center.
- The cyclic silene 2 was successfully used as a hole-injection layer in a functional light-emitting diode.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract The complete scission of strong triple bonds is a definitive hallmark of transition metals, typically remaining beyond the reach of main-group elements. Despite the success of silylenes in activating various inert linkages, the full fragmentation of the isocyanide C≡N moiety by a low-valent silicon center has yet to be realized. Herein, we report that the hypersilyl-stabilized amidinato-silylene, [PhC(NtBu)2SiSi(SiMe3)3] (1), accomplishes the complete cleavage of the C≡N triple bond in xylyl and mesityl isocyanides, providing a new benchmark for silicon-mediated small-molecule activation. We also demonstrate remarkably divergent reactivity where the isocyanide substituent dictates the product formation: aryl isocyanides undergo a complex multistep rearrangement and simultaneous C≡N and Si–Si bond scission to yield novel cyclic silenes (2 and 3) in high yield, whereas cyclohexyl isocyanide leads to a stable insertion product (4) keeping the oxidation state of silicon intact. Such an insertion reaction contrasts with common reports on the reactivity of low-valent silicon compounds, which are regularly oxidized to a more stable higher oxidation state. Finally, we reveal the successful integration of the cyclic silene 2 as a hole-injection layer in a functional light-emitting diode device.
The authors' abstract, as published at the source. JACS Au, 2026 · DOI ↗
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Field: Inorganic Chemistry
Inorganic ChemistryChemistry