Synthesis and structural features of thiophene-fused analogues of warped nanographene and quintuple helicene

Hsing An Lin, Kenta Kato, Yasutomo Segawa*, Lawrence T. Scott, Kenichiro Itami

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Thiophene-fused analogues of warped nanographene (WNG) and quintuple helicene (QH) were synthesized via a three-step π-extension of corannulene. Similar to the synthetic route to WNG, five hexagons and five heptagons were generated by a Scholl reaction of pentakis(thienylphenyl)corannulene to form pentathiaWNG. In contrast, decathiaWNG could not be obtained from pentakis(thienylthienyl)corannulene, and instead decathiaQH was generated from the photocyclization of the precursor. X-ray crystallography of the products revealed their conformations and packing modes in the solid state. The configurational features of decathiaQH were further examined by DFT calculations. The absorption and fluorescence spectra of the sulfur-containing WNG and QH were shifted relative to those of the corresponding sulfur-free analogues.

Original languageEnglish
Pages (from-to)2326-2330
Number of pages5
JournalChemical Science
Volume10
Issue number8
DOIs
Publication statusPublished - 2019
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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