An efficient and facile synthesis of highly substituted 2,6-dicyanoanilines.
A one-pot procedure for the synthesis of substituted 2,6-dicyanoanilines starting from readily available ynones and malononitrile has been developed. For instance, penta-1,4-diyn-3-one is converted into the acetylene-substituted aniline derivative 1 in good yield. Upon photoexcitation, this chromophore shows a strong blue emission with a high quantum yield. The ground- and the excited-state geometries, charge distributions, and excitation energies of 1 have been evaluated by ab initio calculations.
Yi
Chenyi
C
Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Blum
Carmen
C
Liu
Shi-Xia
SX
Frei
Gabriela
G
Neels
Antonia
A
Renaud
Philippe
P
Leutwyler
Samuel
S
Decurtins
Silvio
S
D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003485:Cyanates / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013057:Spectrum Analysis
D000814:Aniline Compounds; D003485:Cyanates; D008314:Malonates; C030290:malonic acid; C023650:aniline