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Updated: Oct 26, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Electronic Control of Scholl Cyclization Trajectories Enables Direct Access to Trihetero-Quasi[8]circulenes
Raseswari Dash1, Parthasarathy Venkatakrishnan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu600 036, India.
Abstract:
Quasi[8]circulenes remain challenging to access directly from polyaryl precursors because competing Scholl-type cyclization pathways obscure control over the annulation sequence. Here, we demonstrate that (hetero)aryl electronic programming directs oxidative cyclodehydrogenation to selectively generate S-, O-, and N-embedded quasi[8]circulenes from tailored tetrarylthiophenes. The resulting twisted π-architecture possesses induced paratropic COT cores, tunable optoelectronic properties, and persistent π-delocalized radical cations with near-infrared (NIR) absorption. Beyond hetero-quasi[8]circulenes, this work establishes electronic programming as a design principle for controlling complexity in oxidative π-framework construction.
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