Effect of different electronic properties on 9-aryl-substituted BMVC derivatives for new fluorescence probes

We have previously illustrated that the electron donor of carbazole moiety and the electron acceptor of methyl pyridinium cation in 3,6-bis(1-methyl-4-vinylpyridinium) carbazole diiodide (BMVC) molecule could form an intramolecular charge-transfer state. The intramolecular twist of the vinyl group in bridging the donor and acceptor plays an important role in the BMVC fluorescence. Here, we have synthesized three 9-aryl-substituted BMVC derivatives with different electronic properties for the design of the second generation of fluorescence probes. The steady-state solvatochromic studies show no appreciable change to the charge transfer of BMVC by substituting an anisole electron-donating group at 9-position of BMVC. However, substituting a 9-nitrobenzyl electron-withdrawing group in BMVC could restrict the charge transfer in the excited state. Moreover, the increase of the fluorescence yields of 9-anisole BMVC and 9-phenyl BMVC upon interaction with DNA is even higher than that in glycerol, while the fluorescence yield of 9-nitrobenzyl BMVC upon interaction with DNA is much lower than that in glycerol. Although 9-nitrobenzyl BMVC is a good G-quadruplex stabilizer, substituting an electron-withdrawing group at 9-position of BMVC is not recommended for the design of fluorescence probes. On the other hand, colocalization between 9-phenyl BMVC and MitoTracker Red in the merged image of cells indicates that the 9-phenyl BMVC is a potential fluorescent mitochondrial probe. (C) 2007 Elsevier B.V. All rights reserved.