A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Autor:	Mikhail M. Evseev, Eugene K. Bashkirov, Bo Xu, Utuq Ablikim, Musahid Ahmed, Ralf I. Kaiser, Alexander M. Mebel, Long Zhao, Valeriy N. Azyazov
Rok vydání:	2020
Předmět:	Reaction mechanism Annulation 010405 organic chemistry Chemistry General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Phenacene Catalysis 0104 chemical sciences Molecular wire chemistry.chemical_compound Tetracene Helicene Computational chemistry Vinylacetylene
Zdroj:	Angewandte Chemie International Edition. 59:4051-4058
ISSN:	1521-3773 1433-7851
DOI:	10.1002/anie.201913037
Popis:	A unified low-temperature reaction mechanism on the formation of acenes, phenacenes, and helicenes-polycyclic aromatic hydrocarbons (PAHs) that are distinct via the linear, zigzag, and ortho-condensed arrangements of fused benzene rings-is revealed. This mechanism is mediated through a barrierless, vinylacetylene mediated gas-phase chemistry utilizing tetracene, [4]phenacene, and [4]helicene as benchmarks contesting established ideas that molecular mass growth processes to PAHs transpire at elevated temperatures. This mechanism opens up an isomer-selective route to aromatic structures involving submerged reaction barriers, resonantly stabilized free-radical intermediates, and systematic ring annulation potentially yielding molecular wires along with racemic mixtures of helicenes in deep space. Connecting helicene templates to the Origins of Life ultimately changes our hypothesis on interstellar carbon chemistry.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c8d66c2f90f4fbe5cba1062824264a18 https://doi.org/10.1002/anie.201913037 Zobrazit plný text záznamu Plný text