Реакция #324368

Уравнение реакции

2,9-dimethyl-1,10-phenanthroline

2-thiophene carboxaldehyde

→

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

Растворители

acetic anhydride

Условия реакции

Обработка

1. 1
   Температураwas refluxed for 5 h
2. 2
   Другоеto give pale yellow solid
3. 3
   ФильтрацияThe solid was filtered off under suction
4. 4
   Промывкаthe filter cake was washed with tetrahydrofuran
5. 5
   ДругоеThis was transferred into a conical flask
6. 6
   Фильтрацияfiltered off under suction
7. 7
   ПромывкаThe solid was again washed with tetrahydrofuran and petroleum ether (40-60° C.)
8. 8
   ДругоеThe product was dried under vacuum at 80° C. for 8 hours
9. 9
   Другоеto give a yellow-orange solid exhibiting intense yellow fluorescence
10. 10
    ДругоеIts absorption and fluorescence spectra in thin film

Методика

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.

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