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

Timofey Chmovzh,Ilya Taydakov,Oleg Rakitin,Vladislav Korshunov

doi:10.3390/m1332

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.

Highlights

Organic π-conjugated molecules have attracted significant attention for the construction of various organic optoelectronic devices (OPVs), such as organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), organic solar cells (OSCs), and others [1,2,3]
Of the numerous combinations of donor, acceptor, and π-spacer building blocks, molecules with the D-π-A-π-D configuration are being intensively studied as donors for OPVs due to their low-lying HOMOs and small band gap [4,5,6]
We report the synthesis of 4,7-bis(5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4d]pyridazine 1 by bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine 2 followed by Suzuki cross-coupling with carbazole boronic acid

Summary

Introduction

Organic π-conjugated molecules have attracted significant attention for the construction of various organic optoelectronic devices (OPVs), such as organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), organic solar cells (OSCs), and others [1,2,3]. It was shown that when using N-bromosuccinimide (NBS) in CHCl3 at room temperature, the yield of the bis-bromo The bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine 2 with several brominating agents was studied (Scheme 1, Table 1).

Results

Conclusion