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Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way
Author(s) -
Zhao Long,
Prendergast Matthew B.,
Kaiser Ralf I.,
Xu Bo,
Ablikim Utuq,
Ahmed Musahid,
Sun BingJian,
Chen YueLin,
Chang Agnes H. H.,
Mohamed Rana K.,
Fischer Felix R.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909876
Subject(s) - triphenylene , biphenyl , fluoranthene , radical , carbon fibers , acetylene , naphthalene , photochemistry , hydrogen atom abstraction , chemistry , aromaticity , materials science , organic chemistry , molecule , composite number , composite material , anthracene
Abstract Polycyclic aromatic hydrocarbons (PAHs) represent the link between resonance‐stabilized free radicals and carbonaceous nanoparticles generated in incomplete combustion processes and in circumstellar envelopes of carbon rich asymptotic giant branch (AGB) stars. Although these PAHs resemble building blocks of complex carbonaceous nanostructures, their fundamental formation mechanisms have remained elusive. By exploring these reaction mechanisms of the phenyl radical with biphenyl/naphthalene theoretically and experimentally, we provide compelling evidence on a novel phenyl‐addition/dehydrocyclization (PAC) pathway leading to prototype PAHs: triphenylene and fluoranthene. PAC operates efficiently at high temperatures leading through rapid molecular mass growth processes to complex aromatic structures, which are difficult to synthesize by traditional pathways such as hydrogen‐abstraction/acetylene‐addition. The elucidation of the fundamental reactions leading to PAHs is necessary to facilitate an understanding of the origin and evolution of the molecular universe and of carbon in our galaxy.