Novel stilbene-based Fischer base analog of leuco-TAM - (2E,2′Z)-{2-(4-(E)-styrylphenyl)propane-1,3-diylidene}bis(1,3,3-trimethylindoline) - derivatives: synthesis and structural consideration by 1D NMR and 2D NMR spectroscopy

We report the synthesis of a series of novel stilbene‐based (St) Fischer base analogs of leuco‐triarylmethane (LTAM) dyes by treating Fischer base with (E)‐4‐styrylbenzaldehyde derivatives. All St‐LTAM molecules examined herein are characterized by 1D and 2D NMR. They were found to exhibit ZE config...

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Bibliographic Details
Published in:Magnetic resonance in chemistry 2016-02, Vol.54 (2), p.143-150
Main Authors: Keum, Sam-Rok, Lim, Hyun-Woo
Format: Article
Language:English
Subjects:
COSY
diastereomeric isomerization
Fischer base analogs of leuco-TAM dyes
Heck reaction
HETCOR
HMBC
malachite green
NMR
NOESY
photochemotherapy agents
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Summary:We report the synthesis of a series of novel stilbene‐based (St) Fischer base analogs of leuco‐triarylmethane (LTAM) dyes by treating Fischer base with (E)‐4‐styrylbenzaldehyde derivatives. All St‐LTAM molecules examined herein are characterized by 1D and 2D NMR. They were found to exhibit ZE configuration and isomerize to their diastereomers EE and ZZ in 2–3 h. They exhibit type I behavior of diastereomeric isomerization. Copyright © 2015 John Wiley & Sons, Ltd. Novel stilbene‐based Fischer base analogs of leuco‐TAM were synthesized and characterized by 1D and 2D NMR spectroscopy. All St‐LTAM molecules exhibited ZE configuration and type 1 behavior, namely, to isomerize to EE and ZZ diastereomers in 2–3 h.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.4359