Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties

Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-b][1]benzofuran-10,10′-indeno[1,2-b][1]benzothiophene] as a new family of spiro-fused PACs t...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-08, Vol.27 (16), p.5103
Main Authors: Nakano, Koji, Takase, Ko, Noguchi, Keiichi
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzofuran
Benzothiophene
Chemical engineering
Chemical engineering research
Chemical properties
chiral compound
Chirality
Circular polarization
furan
Furans
Metamorphosis
nucleophilic aromatic substitution
Optical properties
Organic light emitting diodes
Oxidation
Polycyclic aromatic compounds
Production processes
pyrrole
Solvents
spiro π-conjugated compound
thiophene
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Summary:Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-b][1]benzofuran-10,10′-indeno[1,2-b][1]benzothiophene] as a new family of spiro-fused PACs that contains a furan unit. The compound was successfully synthesized in enantiopure form and also transformed to its S,S-dioxide derivative and the pyrrole-containing analog via aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are apparently different from those of their thiophene analogs that have been reported, owing to the increased electron-richness of furan compared to thiophene. All of the furan-containing chiral spiro-fused PACs were found to be circularly polarized luminescent materials.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27165103