4.7 Article

Double π-Extended Helicene Derivatives Containing Pentagonal Rings: Synthesis, Crystal Analyses, and Photophysics

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 24, Pages 17535-17542

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00989

Keywords

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Funding

  1. National Natural Science Foundation of China [21442010, 21672051, 11704024, 21973024]
  2. Natural Science Foundation of Hebei Province for Distinguished Young Scholar [B2017201072]
  3. Key Project of the Natural Science Foundation of Hebei Province [B2021201043]
  4. Natural Science Foundation of Hebei Province [B2020201044, B2020201006]
  5. Key Research Projects of Science and Technology in Universities of Hebei Province [ZD2020128]
  6. Talent Training Project of Hebei Province [A201902006]
  7. Advanced Talents Incubation Program of the Hebei University [521000981133]
  8. Post-Graduate's Innovation Ability Cultivation Fund Project of Hebei Education Department [HBU2021ss021]

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Two novel double pi-extended [n]helicene (n = 5, 6) derivatives including pentagonal rings were synthesized and characterized, and their crystal structures revealed offset packing models. Optical resolution was performed on one compound, followed by the examination of their chiroptical properties and DFT calculations.
Two novel double pi-extended [n]helicene (n = 5, 6) derivatives (7b and 9) including pentagonal rings have been synthesized and characterized. Both of them have three isomers containing two enantiomers (P-6), (M-6), and a diastereoisomer in a meso form (P,M). X-ray single crystal analyses suggest that molecules 7b and 9 exhibit offset packing models of (P-6,P-5)- and (M-6,M-5)-isomers. Optical resolution of the resultant compound 7b was finished, and their chiroptical properties, as well as the DFT calculations, were also examined.

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