We report the role of the molecular structure and molecular interactions of linear shaped bi-1,3,4-oxadiazole derivatives (BOXD-n) on their self-assembly behaviors and optical properties. The terminal chains of BOXD-n (n = 1, 4) play an important role in molecular self-assembling and their optical properties. High fluorescence efficiency (ΦF = 56%) was observed in BOXD-4 single crystal, while relatively low fluorescence efficiency (ΦF = 21%) was observed in BOXD-1 single crystal. Highly polarized fluorescence (Imax/Imin of 23) and deep blue ASE (λ = 403 nm, threshold of about 20 kW cm−2) were observed in BOXD-4 single crystal, in which molecules uniaxially J-type aggregate through both face-to-face and edge-to-edge π–π interactions between 1,3,4-oxadiazole rings and phenyl rings. No polarized fluorescence or ASE phenomenon was observed in BOXD-4 vacuum evaporated films.
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