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Ti‐Catalyzed Hydroamination for the Synthesis of Amine‐Containing π‐Conjugated Materials
Author(s) -
Hao Han,
Thompson Kyle A.,
Hudson Zachary M.,
Schafer Laurel L.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704500
Subject(s) - hydroamination , conjugated system , solvatochromism , chemistry , catalysis , tautomer , amine gas treating , enamine , photochemistry , molecule , combinatorial chemistry , organic chemistry , polymer
A series of conjugated enamines were prepared by Ti catalyzed anti‐Markovnikov hydroamination. The synthetic route is efficient with yields of up to 94 % and the 100 % atom efficiency of the reaction means that these products are easily isolated and purified. Due to the extended conjugated system, the enamine tautomers were observed exclusively in both solid and solution phases, as determined by X‐ray crystallography and NMR spectroscopy. These new conjugated molecules, with N incorporated into the backbone, show interesting photophysical properties including photo‐luminescent quantum yields of up to 0.26. Notably, through the incorporation of B to give a donor–acceptor π‐conjugated system, a redshift of approximately 100 nm is observed for the emission maximum along with the anticipated solvatochromic shifts.