Réaction #324368

Équation de réaction

2,9-dimethyl-1,10-phenanthroline

2-thiophene carboxaldehyde

→

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

Solvants

acetic anhydride

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed for 5 h
2. 2
   Autreto give pale yellow solid
3. 3
   FiltrationThe solid was filtered off under suction
4. 4
   Lavagethe filter cake was washed with tetrahydrofuran
5. 5
   AutreThis was transferred into a conical flask
6. 6
   Filtrationfiltered off under suction
7. 7
   LavageThe solid was again washed with tetrahydrofuran and petroleum ether (40-60° C.)
8. 8
   AutreThe product was dried under vacuum at 80° C. for 8 hours
9. 9
   Autreto give a yellow-orange solid exhibiting intense yellow fluorescence
10. 10
    AutreIts absorption and fluorescence spectra in thin film

Mode opératoire

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.

Source