We review the present status of experiments and calculations for circularly polarized luminescence (CPL) of simple organic molecules and of stimuli-responsive organic molecules. Together with the historical report of the main instrumental approaches, a few crucial points about experiments are tackled, with the aim of defining measurement protocols, in view of the wide availability of commercial apparatuses in the near future. The calculations aimed at interpreting the CPL spectra, mostly based on time-dependent Density Functional Theory (TD-DFT) calculations, which started around 2010, are reviewed, limiting the discussion to small to mid-sized molecules. Some applications of CPL spectra of organic molecules-based systems are presented, with a focus especially on two fields: material science and biology. Chirality 28:696-707, 2016. © 2016 Wiley Periodicals, Inc.

The new inherently chiral material shows outstanding chirality manifestations with chiral probes, as well as with circularly polarized light components and electron spins.

The absolute configuration (AC) of the bioactive metabolites phyllostin (1) and scytolide (2), two hexahydro-1,4-benzodioxines produced by Phyllosticta cirsii, and oxysporone (3), a dihydrofuropyranone recently isolated from a strain of Diplodia africana, has been assigned by computational analysis of their optical rotatory dispersion (ORD), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) spectra. Computational prediction of ORD, ECD, and VCD allowed us to assign (3S,4aR,8S,8aR) AC to naturally occurring (-)-1, while (4aR,8S,8aR) AC was assigned to (-)-2 employing only ECD and VCD, because in this case ORD analysis turned out to be unsuitable for AC assignment. Theoretical prediction of both ORD and ECD spectra of 3 led to assignment of (4S,5R,6R) AC to (+)-3. In this case a satisfactory agreement between experimental and calculated VCD spectra was obtained only after taking into account solvent effects. This study shows that in the case of flexible and complex natural products only a concerted application of more than a single chiroptical technique permits unambiguous assignment of absolute configuration.