Synthesis of the First Chiral Bisindolyl Monomethinium Cyanine Dyes | Zendy

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Synthesis of the First Chiral Bisindolyl Monomethinium Cyanine Dyes

Author(s) -

Eggers Lutz,

Buß Volker

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960618

Subject(s) - cyanine , chemistry , diastereomer , salt (chemistry) , indole test , stereochemistry , proton nmr , nuclear magnetic resonance spectroscopy , spectroscopy , organic chemistry , physics , quantum mechanics , fluorescence

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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