2017
DOI: 10.1002/ange.201708429
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Closed Pentaaza[9]helicene and Hexathia[9]/[5]helicene: Oxidative Fusion Reactions of ortho‐Phenylene‐Bridged Cyclic Hexapyrroles and Hexathiophenes

Abstract: Oxidative fusion reactions of ortho‐phenylene‐bridged cyclic hexapyrroles and hexathiophenes furnished novel closed helicenes in a selective manner. X‐Ray diffraction analysis unambiguously revealed the structures to be a closed pentaaza[9]helicene, the longest azahelicene reported so far, and an unexpected double‐helical structure of hexathia[9]/[5]helicene, whose formation was assumed to result from multiple oxidative fusion along with a 1,2‐aryl shift. The pentaaza[9]helicene exhibited well‐defined emission… Show more

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Cited by 26 publications
(19 citation statements)
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“…As imilar fusion reactionw as also used for the synthesis of a,a'-dibromotribenzotetrathia [7]helicene 4 by BF 3 ·OEt 2 -promoted oxidation of linear tetrathiophene 3 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (Scheme 1c). [9] Then,w es et out to examinet he oxidative fusionr eactions of 1,2-phenylene-bridged tripyrrolic precursors as shown in Scheme 1d.H erein, we report the synthesis, structures,a nd optical properties of novela zahelicene and azahepta [8]circulene derivatives, the latter of which were unexpectedly obtained during our course of study.…”
Section: Introductionmentioning
confidence: 93%
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“…As imilar fusion reactionw as also used for the synthesis of a,a'-dibromotribenzotetrathia [7]helicene 4 by BF 3 ·OEt 2 -promoted oxidation of linear tetrathiophene 3 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (Scheme 1c). [9] Then,w es et out to examinet he oxidative fusionr eactions of 1,2-phenylene-bridged tripyrrolic precursors as shown in Scheme 1d.H erein, we report the synthesis, structures,a nd optical properties of novela zahelicene and azahepta [8]circulene derivatives, the latter of which were unexpectedly obtained during our course of study.…”
Section: Introductionmentioning
confidence: 93%
“…[6] In ad ifferent strategy,w er ecently reported an oxidativef usion reactiono f1 ,2-phenylene-bridged cyclic pyrrole oligomers to form fused pyrrolic skeletons. Oxidationr eaction of cyclic tetramer 1 with DDQ in the presence of Sc(OTf) 3 affordedt etraaza [8]circulene TA8C exclusively, [7] while similaro xidationof 1,2-phenylene-bridgedc yclic pyrrole hexamer 2 gave closedpentaaza [9]helicene PA9H in am oderate yield (Scheme 1a,b). [8] As demonstrated in these examples, the resulting PHA productsc an be designed by choice of precursors, which drove us to explore more facile syntheses of pyrrole-incorporated PHAs.…”
Section: Introductionmentioning
confidence: 99%
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