Abstract
AbstractA series of C2‐symmetrical aza‐analogous 1,4‐distyrylbenzenes were synthesised via two‐fold PO‐activated olefinations or Heck reactions. Pyridine, pyrimidine and quinoline were used as terminal rings, and the 2,5‐positions of the central benzene ring were substituted with H, alkoxy, or alkylsulfonyl groups. These strongly fluorescent compounds are freely soluble in common solvents such as toluene or chloroform. Whereas the electronic spectra of the pyridine and pyrimidine chromophores were very similar to those of the parent compound 1,4‐distyrylbenzene, the spectra of the former were altered considerably in the presence of trifluoroacetic acid. Depending on the concentration of the acid, protonation of the ground state and/or the excited state caused bathochromic shifts of the absorption and the emission spectra, accompanied by reductions in the fluorescence efficiencies. Copyright © 2004 John Wiley & Sons, Ltd.
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