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

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 p...

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Detalles Bibliográficos
Autores principales: Lin, Hsing-An, Kato, Kenta, Segawa, Yasutomo, Scott, Lawrence T., Itami, Kenichiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385676/
https://www.ncbi.nlm.nih.gov/pubmed/30881659
http://dx.doi.org/10.1039/c8sc04470h
Descripción
Sumario: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.