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Issue 8, 2019
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Synthesis and structural features of thiophene-fused analogues of warped nanographene and quintuple helicene

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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.

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

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Publication details

The article was received on 08 Oct 2018, accepted on 18 Dec 2018 and first published on 19 Dec 2018


Article type: Edge Article
DOI: 10.1039/C8SC04470H
Citation: Chem. Sci., 2019,10, 2326-2330
  • Open access: Creative Commons BY-NC license
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    Synthesis and structural features of thiophene-fused analogues of warped nanographene and quintuple helicene

    H. Lin, K. Kato, Y. Segawa, L. T. Scott and K. Itami, Chem. Sci., 2019, 10, 2326
    DOI: 10.1039/C8SC04470H

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