4,7-Bis(5-(9-hexyl-9<em>H</em>-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-<em>d</em>]pyridazine

Abstract

Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazoleboronic acid gave 4,7-bis( 5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine. The structure of the newly synthesized compounds was established by high resolution mass-spectrometry, 1H, 13C NMR, IR, and UV spectroscopy and mass-spectrometry. A study of the luminescent properties of the dye showed that it exhibits fluorescence in the near infrared region of the spectrum, which makes it a promising compound for use as an active emitting layer in NIR OLED as well as for other possible applications as an IR luminophore.

Keywords

• [1,2,5]thiadiazolo[3,4-<i>d</i>]pyridazine
• Suzuki cross-coupling
• thiophene
• carbazole
• luminescence