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Synthesis of Water‐Soluble Blue‐Emissive Tricyclic 2‐Aminopyridinium Salts by Three‐Component Coupling‐(3+3)‐Anellation
Author(s) -
Bakulina Olga,
Merkt Franziska K.,
Knedel TimOliver,
Janiak Christoph,
Müller Thomas J. J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808665
Subject(s) - tricyclic , dichloromethane , chemistry , component (thermodynamics) , luminophore , luminescence , organic chemistry , materials science , optoelectronics , physics , solvent , thermodynamics
The (3+3) anellation of alkynones and cyclic amidines is a novel and unexpected approach to generate intensively blue luminescent tricyclic 2‐aminopyridinium salts with quantum yields Φ f up to 63 % in water. By implementation into a consecutive three‐component reaction, these title compounds are obtained rapidly and efficiently in a diversity‐oriented fashion. Most interestingly, these bi‐ and tricyclic 2‐aminopyridinium salts emit in dichloromethane and water solutions, thus making them interesting novel luminophore probes for bioanalytics, as well as in the solid state, thus making them blue emitters with tunable efficiency.