Supramolecular Assembly of An Organoplatinum(II) Complex with Ratiometric Dual Emission for Two-Photon Bioimaging

The organoplatinum(II) complex [Pt((CNN)-N-boolean AND-N-boolean AND)(Cl)] ((CNN)-N-boolean AND-N-boolean AND=5,6-diphenyl-2,2 '-bipyridine, Pt1) can assemble into nanoaggregates via pi-pi stacking and complementary hydrogen bonds, rather than Pt-Pt interactions. Pt1 exhibits ratiometric dual emission, including rare blue emission (lambda(em)=445 nm) and assembly-induced yellow emission (lambda(em)=573 nm), under one- and two-photon excitation. Pt1 displays blue emission in cells with an intact membrane due to its low cellular uptake. In cells where the membrane is disrupted, uptake of the complex is increased and at higher concentrations yellow emission is observed. The ratio of yellow to blue emission shows a linear relationship to the loss of cell membrane integrity. Pt1 is, to our knowledge, the first example of an assembly-induced two-photon ratiometric dual emission organoplatinum complex. The excellent and unique characteristics of the complex enabled its use for the tracking of cell apoptosis, necrosis, and the inflammation process in zebrafish.