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A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
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https://doi.org/10.1002/anie.202003402Abstract
A representative, low-temperature gas-phase reaction mechanism synthesizing polyacenes via ring annulation exemplified by the formation of pentacene (C22 H14 ) along with its benzo[a]tetracene isomer (C22 H14 ) is unraveled by probing the elementary reaction of the 2-tetracenyl radical (C18 H11 . ) with vinylacetylene (C4 H4 ). The pathway to pentacene-a prototype polyacene and a fundamental molecular building block in graphenes, fullerenes, and carbon nanotubes-is facilitated by a barrierless, vinylacetylene mediated gas-phase process thus disputing conventional hypotheses that synthesis of polycyclic aromatic hydrocarbons (PAHs) solely proceeds at elevated temperatures. This low-temperature pathway can launch isomer-selective routes to aromatic structures through submerged reaction barriers, resonantly stabilized free-radical intermediates, and methodical ring annulation in deep space eventually changing our perception about the chemistry of carbon in our universe.
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