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

HRID 237186

Reaktionsgleichung

Reaktionsgleichung von HRID 237186
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][C:7]([CH3:16])=[N:6]3)[N:3]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH:22]=O>C(OC(=O)C)(=O)C>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH:22]=[CH:16][C:7]1[CH:8]=[CH:9][C:10]2[C:5](=[C:4]3[C:13](=[CH:12][CH:11]=2)[CH:14]=[CH:15][C:2]([CH:1]=[CH:22][C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)=[N:3]3)[N:6]=1

Komponenten

4

Edukt 2

HCID 73642-ThiophenecarboxaldehydeHCID 652372,9-Dimethyl-1,10-phenanthroline

Produkt 1

HCID 668665812,9-Bis(2-thiophen-2-yl-vinyl)-[1,10]phenanthroline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturewas refluxed for 5 h
  2. customto give pale yellow solid
  3. filtrationThe solid was filtered off under suction
  4. washthe filter cake was washed with tetrahydrofuran
  5. customThis was transferred into a conical flask
  6. filtrationfiltered off under suction
  7. washThe solid was again washed with tetrahydrofuran and petroleum ether (40-60° C.)
  8. customThe product was dried under vacuum at 80° C. for 8 hours
  9. customto give a yellow-orange solid exhibiting intense yellow fluorescence
  10. customIts absorption and fluorescence spectra in thin film

Quellen und Nachweise

ORD-Eintrag
ord-e35efaca0df54e60a48fb2dce82304d9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642188B2

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