[1]Benzothiophene-Fused Chiral Spiro Polycyclic Aromatic Compounds: Optical Resolution, Functionalization, and Optical Properties

Spiro polycyclic aromatic compounds
have been known as rigid chiral
scaffolds. In order to extend their applications, an efficient preparation
route to enantiopure derivatives is highly required. Here, we design
10,10′-spirobi­[indeno­[1,2-b]­[1]­benzothiophene]-7,7′-diol
to achieve efficient optical resolution. The compound was successfully
synthesized and resolved by chiral HPLC on a semipreparative scale.
The absolute configuration of its enantiopure isomer was determined
through single-crystal X-ray structure analysis of its derivative.
The compound was also transformed into its derivatives with donor–acceptor
(D–A) type systems. The obtained chiral D–A type molecules
exhibited remarkable solvent-dependence fluorescence and were found
to be solvent-sensitive circularly polarized luminescent materials.
These results clearly demonstrated the utility of 10,10′-spirobi­[indeno­[1,2-b]­[1]­benzothiophene]-7,7′-diol as a versatile building
block for chiral spiro polycyclic aromatic compounds.