LAUSR

Abstract Circular dichroism (CD) and circular polarized luminescence (CPL) are useful for various applications. However, it is difficult to achieve excellent CD and CPL in differently polar solvents simultaneously. This work provides a simple but efficient way to construct violet-blue fluorescent and water-soluble chromophore through the construction of rigid conformation of the alkyne architecture. By introducing proline pendants into alkyne architecture, the chromophore exhibits reasonable CD and CPL properties in the lowly and highly polar solvents. More importantly, even in water, the chromophore displays effective CD anisotropy factor (g abs  ∼ 1 × 10 −3 ) and luminescence dissymmetry factor (g lum  ∼ 2 × 10 −3 ), as well as high fluorescence quantum yield (Φ up to 35%). Additionally, the chromophore exhibits large two-photon CD according to the theoretically calculated results. The excellent chiroptical properties from the simple organic fluorophore enables its future applications in miniatured optoelectronic devices and CPL-based bioimaging.