Repercussions of multi-electron uptake by a twistacene: a reduction-induced double dehydrogenative annulation
Literature Information
Publication Date
2023-09-22
DOI
10.1039/D3QO01282D
Impact Factor
5.281
Authors
Matthew Pennachio, Zheng Wei, Robert G. Clevenger, Kathleen V. Kilway, Alexandra Tsybizova, Renana Gershoni-Poranne, Marina A. Petrukhina
View Original
Abstract
Chemical reduction of highly-twisted 9,10,11,20,21,22-hexaphenyltetrabenzo[a,c,l,n]pentacene (C74H46, 1) was investigated using Li and Cs metals as the reducing agents. The Cs-induced reduction of 1 in the presence of 18-crown-6 ether enabled the isolation of a solvent-separated ion pair (SSIP) with a “naked” monoanion. Upon reduction with Li metal, a double reductive dehydrogenative annulation of 1 was observed to afford a new C74H422− dianion. The latter was shown to undergo a further reduction to C74H424− without additional core transformation. All products were characterized by single-crystal X-ray diffraction and spectroscopic methods. Subsequent in-depth theoretical analysis of one vs. two and four electron uptake by 1 provided insights into how the changes of geometry, aromaticity and charge facilitated the core transformation of twistacene observed upon two-fold reduction. These experimental and theoretical results pave the way to understanding of the reduction-induced core transformations of highly twisted and strained π-systems.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate
CAS Number:
211429-79-7
Molecular Formula:
C15H17NO3
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