A series of terpyridine-based zinc(ii) complexes assembled for third-order nonlinear optical responses in the near-infrared region and recognizing lipid membranes.

Two-photon (TP) microscopy has advantages for biological imaging in that it allows deeper tissue-penetration and excellent resolution compared with one-photon (OP) microscopy. Herein, two-photon activated nonlinear optical (NLO) materials, a terpyridine derivative ligand with a donor-acceptor (D-A) model and its corresponding four zinc(ii) complexes (Z1-Z4), were assembled and fully characterized. Based on their systematic photophysical investigations, it was found that the third-order NLO response in the near-infrared (NIR) region was significantly enhanced for the symmetrical complex Z4 compared with the other asymmetric complexes (Z1-Z3). To further explore its utility in biological systems, Z4 was selected as a two-photon probe for cellular lipid membranes, which was confirmed both by two-photon confocal microscopy and transmission electron microscopy (TEM). Furthermore, it was found that the fluorescence intensity was enhanced for complex Z4 with the addition of bioactive liposomes (1 μg mL). Its recognition mechanism was demonstrated by experimental methods, as well as molecular modeling calculations. These findings should open a new pathway for functional metal complexes as lipid membrane targeting probes.