Synthesis and Properties of Bis(naphthofuran)-Fused [7]Helicene Derivatives
Issued Date
2023-01-24
Resource Type
ISSN
1434193X
eISSN
10990690
Scopus ID
2-s2.0-85146311989
Journal Title
European Journal of Organic Chemistry
Volume
26
Issue
4
Rights Holder(s)
SCOPUS
Bibliographic Citation
European Journal of Organic Chemistry Vol.26 No.4 (2023)
Suggested Citation
Hashmi Y., Thongpanchang T. Synthesis and Properties of Bis(naphthofuran)-Fused [7]Helicene Derivatives. European Journal of Organic Chemistry Vol.26 No.4 (2023). doi:10.1002/ejoc.202201373 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/81755
Title
Synthesis and Properties of Bis(naphthofuran)-Fused [7]Helicene Derivatives
Author(s)
Author's Affiliation
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Abstract
Novel benzo[1,2-b:4,3-b′]dinaphthofuran (oxa[7]helicene) with various substituents in the central ring were designed and successfully synthesized based on the late stage central ring formation strategy from naphthofuranoneby using an efficient McMurry coupling or Friedel-Crafts acylation. The photochemical properties of helicenes were evaluated by UV-Visible absorption spectroscopy and fluorescence spectroscopy, while electrochemical behaviour including their energy profile were investigated by cyclic voltammetry and DFT calculations. According to the computational study, substituents on the central ring could influence both electron delocalization and MO distribution of oxa[7]helicenes resulting in the change in charge transporting ability. In comparison to the parent carbo[7]helicene, the furan unit in conjunction with substituents on helical system caused the bathochromic shift with different absorption pattern and exhibited higher fluorescence quantum yield (ϕf up to 0.63). These new materials showed promising characteristics in optoelectronic application.