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Synthesis of the First Chiral Bisindolyl Monomethinium Cyanine Dyes

✍ Scribed by Eggers, Lutz ;Buß, Volker

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
485 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The synthesis of the chiral monomethine cyanine dyes 8 and 9 starting with the achiral indole 1 is described. Key intermediates are the new chiral Fischer bases R‐ and S‐4, which were separated after diastereomeric salt formation. The conformation of the dyes 8 and 9 is twisted di‐Z, according to NOE and dynamic NMR spectroscopy. The free energy difference between oppositely twisted conformations is ca. 2.5 kJ mol^−1^.

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