Reacción #324368

Ecuación de reacción

2,9-dimethyl-1,10-phenanthroline

2-thiophene carboxaldehyde

→

2,9-Bis(2-thiophen-2-yl-vinyl)-[1,10]phenanthroline

Disolventes

acetic anhydride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 5 h
2. 2
   Otroto give pale yellow solid
3. 3
   FiltraciónThe solid was filtered off under suction
4. 4
   Lavadothe filter cake was washed with tetrahydrofuran
5. 5
   OtroThis was transferred into a conical flask
6. 6
   Filtraciónfiltered off under suction
7. 7
   LavadoThe solid was again washed with tetrahydrofuran and petroleum ether (40-60° C.)
8. 8
   OtroThe product was dried under vacuum at 80° C. for 8 hours
9. 9
   Otroto give a yellow-orange solid exhibiting intense yellow fluorescence
10. 10
    OtroIts absorption and fluorescence spectra in thin film

Procedimiento

A mixture of 2,9-dimethyl-1,10-phenanthroline (neocuproine hydrate) (10 g, 0.048 mole) and 2-thiophene carboxaldehyde (9.4 ml, 0.188 mole) in acetic anhydride (15 ml) was refluxed for 5 h. The solution was allowed to cool to room temperature to give pale yellow solid. The solid was filtered off under suction and the filter cake was washed with tetrahydrofuran. This was transferred into a conical flask, stirred with de-ionised water for 15 minutes and filtered off under suction. The solid was again washed with tetrahydrofuran and petroleum ether (40-60° C.). The product was dried under vacuum at 80° C. for 8 hours. Yield: 5.9 g. The product was sublimed to give a yellow-orange solid exhibiting intense yellow fluorescence. Its absorption and fluorescence spectra in thin film and in solution in THF are shown in FIGS. 1 and 2.

Fuente