Design, synthesis, linear and nonlinear photophysical properties and biological imaging application of a novel Λ-type pyrimidine-based thiophene derivative

• A novel D–π–A–π–D type thiophene pyrimidine derivative (L) was obtained.
• L belongs to P212121 non-centrosymmetric space group.
• L shows strong third-order nonlinear optical response.
• L is capable of detecting the cytoplasm section in HepG2 cells.

A novel D–π–A–π–D type thiophene pyrimidine derivative, 2,2′-thiophene-4, 6-bis (4-N,N-diethylbenzene ethenyl) pyrimidine (L), was designed, synthesized via Knoevenagel and Suzuki coupling reactions, and fully characterized. The results of X-ray diffraction analysis revealed that single crystal of L belongs to P212121 non-centrosymmetric space group, and the whole molecular skeleton exhibits a good coplanarity. Systematic photophysical properties were investigated for L. The connections between the properties and structure were explained relying on theoretical calculation. The thiophene pyrimidine derivative shows strong third-order nonlinear optical response and large two-photon absorption (2PA) cross section in high polar solvents. Finally, preliminary exploration in biological imaging also has been carried out, it shows a good biological application prospect.

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