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Herstellung, Struktur und Eigenschaften neuartiger kettensubstituierter und chiraler Trimethincyanin‐Farbstoffe mit Indolin‐Endgruppen 1)
Author(s) -
Reichardt Christian,
Engel HorstDetlef,
Allmann Rudolf,
Kucharczyk Damian,
Krestel Magda
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230324
Subject(s) - cyanine , chemistry , indoline , stereochemistry , chirality (physics) , physics , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , fluorescence , quark
Synthesis, Structure, and Properties of Novel Chain‐Substituted and Chiral Trimethine Cyanine Dyes with Indoline End Groups Synthesis and spectroscopic properties of the trimethine cyanine dyes 3, 8a, b , and 13a, b as well as 14a‐c with new substitution patterns are described. Constitutions and configurations of 3, 8a, b and 14c have been determined by X‐ray analyses (Figures 1, 2, and 6). Dye 3 exists in the previously unknown di‐cis ( E, E, Z, Z ) configuration along the methine chain. Attempts to prepare 3 in a base‐catalysed reaction unexpectedly led to the rearranged trimethine cyanine dyes 8a, b with a centre of chirality in one of the indoline end groups. Using this Wagner‐Meerwein rearrangement after resolution, the chiral heterocyclic quaternary salts ( S )‐ 12a‐ c have been prepared, from which the optically active trimethine cyanine dyes ( S,S )‐ 14a‐c have been obtained for the first time. The UV/VIS spectra of 3, 8a and 13a (Figure 7) as well as the CD spectra of 12a and 14a (Figures 3 and 4) are compared and discussed.