- Unsymmetric leuco-TAM dyes, (2E, 2′E)-2,2′-{(E)-4-phenylpent-2- ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives. Part II: X-ray crystal structure
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The unequivocal solid-state structure and stereochemistry of the unsymmetric leuco-triarylmethane (Un-LTAM) dye 2,2′-{(E)-4-(phenyl)pent-2- ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives were established using X-ray single-crystal analysis. Th
- Keum, Sam-Rok,Ma, So-Young,Kim, Do-Kyung,Lim, Hyun-Woo,Roh, Se-Jung
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body text
p. 490 - 495
(2012/06/18)
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- Novel unsymmetrical leuco-TAM, (2E, 2′E)-2,2′-{(E)-4- phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives: Synthesis and structure elucidation
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Novel unsymmetrical leuco-TAM, (2E, 2′E)-2,2′-{(E)-4- phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives were synthesized from a reaction of commercially available 2-methylene-1,3,3- trimethylindoline (FB) and substituted cinnamaldehyde derivatives. The chemical structures of the resulting molecules were determined using 1D and 2D NMR spectroscopy experiments, including COSY, HMBC and NOESY. The compounds had the EEE configuration and were potent precursors for Cy5 TAM+ dyes. This is different from the Malachite green FB-analogs, which generally have a ZE configuration and are precursors to Cy3 TAM+ dyes. The formation of unsymmetrical LTAM molecules as the sole product suggests that the Michael-type addition of a FB molecule occurs on the δ-carbon of the α, β, γ, δ-unsaturated imminium salts, which were formed as an intermediate at the first step.
- Keum, Sam-Rok,Lee, Min-Hyung,Ma, So-Young,Kim, Do-Kyung,Roh, Se-Jung
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experimental part
p. 233 - 238
(2011/12/21)
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