Circularly polarized luminescence of talarolactones (+)/(-)-A and (+)/(-)-C: The application of CPL-calculation in stereochemical assignment

Two pairs of fluorescent natural products, talarolactones (+)/(-)-A and (+)/(-)-C [(+)/(-)-1 and (+)/(-)-2], were discovered and characterized as a new family of circularly polarized luminescence-active small organic molecules (CPL-SOMs) with high fluorescence efficiency and fascinating CPL properties. The CPL (I vertical bar g(lum)vertical bar) levels of enantiomerically pure (+)/(-)-1 and (+)/(-)-2 in solution falls into the usual range (10(-5)-10(-3)) considering their pure organic nature, but the sign of CPL were found to be closely related to the absolute configuration of C-8. The high agreement of the measured CPL spectra of (+)/(-)-1 and (+)/(-)-2 with the time-dependent density functional theory (TDDFT) calculated ones demonstrated the usefulness of CPL-calculation as a unique method for stereochemical assignment. This study may open up a new perspective for the stereochemical studies and the future development of CPL materials. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

A new family of circularly polarized luminescence-active small organic molecules (CPL-SOMs) with high fluorescence efficiency and fascinating CPL properties was discovered and characterized. The usefulness of CPL-calculation as a unique method for stereochemical assignment was demonstrated. This study may open up a new perspective for the future development of stereochemical studies and CPL materials.