Self-assembly of new arene-ruthenium rectangles containing triptycene building block and their application in fluorescent detection of nitro aromatics

A suite of two new tetraruthenium metallarectangles 5 and 6 have been obtained from [2+2] self-assemblies between dipyridylethynyltriptycene 2 and one of the two dinuclear arene ruthenium clips, [Ru-2 (mu-eta(4)-OO boolean AND OO) (eta(6)-p-cymene)(2)][OTf](2); (OO boolean AND OO = oxalate 3; 6,11-dihydroxy-5,12-naphthacenedionato (dotq) 4; OTf = triflate). These molecular rectangles are fully characterized by H-1 NMR spectroscopy, electrospray mass spectrometry. A single crystal of 6 was suitable for X-ray diffraction structural characterization. These new metallarectangles showed fluorescence behavior in solution, have been examined for emission quenching effects with various aromatic compounds, and show high quenching selectivity and sensitivity towards nitroaromatics, particularly picric acid and 1,3,5-trinitrobenzene. Excited-state charge transfer from the rectangles to nitro aromatic substrates can be used to develop selective fluorescent sensors for nitro aromatics. (C) 2014 Elsevier B.V. All rights reserved.