This study synthesizes cyclic and acyclic aromatic triamides with conjugated systems to establish molecular design guidelines for obtaining reliable circularly polarized luminescence (CPL)-active materials. For the compounds with the phenylacetylene unit,the acyclic derivative shows a single fluorescence at 381 nm,whereas the cyclic ones show dual fluorescence. The long-wavelength emission at 545 nm is significant for the compound with three π-conjugated systems measured at 25 °C. The fluores-cence quantum yield and lifetime depend on the number of con-jugated systems introduced into the cyclic structure. When the enantiomers of the cyclic compounds is isolated by chiral high-performance liquid chromatography, all of them shows cir-cular dichroism (CD) activity, but only the compound with the three conjugated systems shows CPL with the anisotropy factor glum = 4.0x10. On the other hand, this study also synthesizes two cyclic aromatic triamides with the naphthylacetylene unit and succeeded in optical resolutions. The fluorescence quantum yields (Φ = 0.80 and 0.34) are improved, and a single sky blue emission is observed. The CD and CPL anisotropy factors are larger than those of the phenyl counterpart, and the CPL shows a B CPL value of about 30 M cm
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