Synthesis of Pyrrole-Containing Chiral Spiro Molecules and Their Optical and Chiroptical Properties

Abstract

Abstract The pyrrole-containing chiral spiro π-conjugated compounds were successfully synthesized from 10,10′-spirobi[indeno[1,2-b][1]benzothiophene] 5,5-dioxide and 5,5,5′,5′-tetraoxide via a sequential inter/intramolecular nucleophilic aromatic substitution with arylamines. The enantiopure ones were also prepared from the enantiopure substrates. UV-vis absorption and photoluminescence spectroscopies and theoretical calculations revealed that the replacement of thiophene unit(s) of 10,10′-spirobi[indeno[1,2-b][1]benzothiophene] with pyrrole unit(s) has a great impact on photophysical properties. The pyrrole-containing chiral spiro π-conjugated compounds exhibited circularly polarized luminescence with a relatively large dissymmetry factor.