Journal
POLYCYCLIC AROMATIC COMPOUNDS
Volume 41, Issue 4, Pages 795-804Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10406638.2019.1622134
Keywords
Aromatic CC coupling; crystal structures; oxidative CH bond activation; polyaromatic hydrocarbons; silver(II) oxidizer
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Funding
- National Science Center of the Republic of Poland (NCN) [UMO-2015/19/B/STS/02863]
- Slovenian Research Agency (ARRS) [P1-0045]
- European Union within the ERDF Project [POIG.02.01.00-14-122/09]
- EU - the European Regional Development Fund within the Operational Program Innovative economy for 2007-2013 [POIG.02.02.00-14-024/08-00]
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9,9 '-bianthryl and 9,9 '-biphenanthryl were synthesized by direct oxidative C-C coupling using divalent silver sulfate Ag(II)SO4 at ambient temperature conditions. Despite low yields of 6-10%, they present a competitive advantage compared to more complex synthetic pathways due to their single-pot process and lower waste generation. X-ray structures of adducts revealed that the aromatic hydrocarbon guest molecules were accommodated in cavities formed by the host 9,9 '-bianthryl molecule, primarily stabilized by C-H···π interactions.
9,9 '-bianthryl and 9,9 '-biphenanthryl were synthesized by direct oxidative C-C coupling of anthracene and phenanthrene, respectively, using divalent silver sulfate Ag(II)SO4 under ambient temperature conditions. Syntheses proceed with rather low yields 6-10%, however, they are competitive to more complex synthetic pathways due to single-pot process and lower waste. The single crystal structures of 9,9 '-bianthryl, 9,9 '-biphenanthryl and adducts of 9,9 '-bianthryl with benzene, toluene and o- and p-xylene were obtained. X-ray structure of the adducts attested that the guest molecules of aromatic hydrocarbons were accommodated in cavities formed by the host 9,9 '-bianthryl molecule. The adducts are stabilized mostly by the C-H center dot center dot center dot pi interactions, as indicated by analysis of crystal structures and Hirschfeld surfaces.
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