Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition.

A new efficient method was proposed for the synthesis of (18-crown-6)stilbene; the structure of the product was confirmed by X-ray diffraction analysis. In MeCN, this compound forms pseudodimeric complexes with -(2-ammonioethyl)-4-styrylpyridinium and -(3-ammoniopropyl)-4-styrylpyridinium diperchlorates via hydrogen bonding between the ammonium group and the crown ether oxygen atoms. The ammonioethyl derivative was synthesized for the first time.

Relaxation Photoprocesses in a Crowned Styryl Dye and its Metal Complex.

The effects of solvent and crown-ether moiety on spectral properties of pyridinium styryl dye were studied by steady-state absorption and fluorescent spectroscopy. Analysis of viscosity and polarity effects on fluorescence quantum yield and Stokes shift permitted us to suggest that there is a two stage process of excited state relaxation. The macrocyclic moiety has a little influence on the first stage of relaxation, which manifests itself in a magnitude of Stokes shift, but suppresses considerably the second stage, which manifests itself in a magnitude of fluorescence quantum yield.

Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes.

Novel 2-benzothiazole-, 4-pyridine-, and 2- and 4-quinoline-based styryl dyes containing an N-methylbenzoaza-15(18)-crown-5(6)-ether moiety were synthesized. A detailed electronic spectroscopy study revealed high performance of these compounds as optical molecular sensors for alkali and alkaline-earth metal cations. They were shown to considerably surpass analogous chromoionophores based on N-phenylaza-crown ethers regarding both the ionochromism and the cation-binding ability.