Synthesis, Crystal Structure and Its Application in Living Cells Imaging of Benz(c)acridine-1,2,3-triazole Derivatives

A highly selective iron ions fluorescent probe based on the benz(c)acridine-1,2,3-triazole derivatives was produced by multi-step reactions. 1-(7-Benz[c]acridinyl)-4-(4-methylphenyl)-1,2,3-triazole (4a), C26H18N4, was structurally determined by single-crystal X-ray diffraction. It crystallizes in the trigonal system, space group R-3 with a = 36.230(10), b = 36.230(10), c = 7.993(3) angstrom, beta = 90 degrees, V = 9086(6) angstrom(3), Z = 18, D-c = 1.271 g/cm(3), F(000) = 3636, mu= 0.602 mm(-1), the final R = 0.0865 and wR = 0.1619 for 3951 observed reflections (I > 2 sigma(I)). X-ray analysis indicated that all four rings of benz(c)acridine are in the same plane, and the 1,2,3-triazole ring and the corresponding linked benzene (C(1)-C(6)-C(7)-C(8)-C(9)-N(1)) are approximately perpendicular with a dihedral angle of 106.5 degrees. The crystal packing of the compound was stabilized by two weak interactions between C(11)-H(10)center dot center dot center dot N(4) and C(18)-H(18)center dot center dot center dot N(1). In fluorescence spectra studies, compound 4c was exhibited good selectivity and sensitivity towards iron ions in DMSO: mops buffer solution. Furthermore, 4c was successfully used for imaging iron ions in living HeLa cervical cancer cells.