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A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
Author(s) -
Zhao Long,
Kaiser Ralf I.,
Lu Wenchao,
Ahmed Musahid,
Evseev Mikhail M.,
Bashkirov Eugene K.,
Azyazov Valeriy N.,
Tönshoff Christina,
Reicherter Florian,
Bettinger Holger F.,
Mebel Alexander M.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202003402
Subject(s) - pentacene , tetracene , annulation , chemistry , gas phase , fullerene , ring (chemistry) , carbon nanotube , photochemistry , carbon fibers , computational chemistry , anthracene , nanotechnology , organic chemistry , materials science , catalysis , electrode , composite material , composite number , thin film transistor
A representative, low‐temperature gas‐phase reaction mechanism synthesizing polyacenes via ring annulation exemplified by the formation of pentacene (C 22 H 14 ) along with its benzo[ a ]tetracene isomer (C 22 H 14 ) is unraveled by probing the elementary reaction of the 2‐tetracenyl radical (C 18 H 11 . ) with vinylacetylene (C 4 H 4 ). 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.