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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201909876
Subject(s) - triphenylene , biphenyl , radical , fluoranthene , chemistry , carbon fibers , acetylene , hydrogen atom abstraction , photochemistry , naphthalene , aromaticity , organic chemistry , molecule , materials science , anthracene , composite number , composite material
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.