7,7’-(4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole)

Nikita S Gudim,Ekaterina A Knyazeva,Олег А Ракитин

doi:10.3390/m1310

Nikita S Gudim, Ekaterina A Knyazeva + Show 1 more

Open Access

https://doi.org/10.3390/m1310

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Abstract

2,6-Bis(benzo[c][1,2,5]thiadiazol-4-yl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophenes are of interest for the synthesis of molecules which can be employed in optoelectronic devices. In this communication, 7,7’-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole) was obtained by direct C–H cross-coupling of 4,7-dibromobenzo[c][1,2,5]thiadiazole with 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene in the presence of palladium(II)acetate and potassium pivalate. The structure of newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy.

Highlights

Π-Conjugated molecules have been often used in organic optoelectronic devices such as organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), organic solar cells (OSCs) and others [1,2]
Direct C–H arylation has been developed as a method for synthesis conjugated materials for use in organic electronics from simple building blocks [15,16,17,18]
This method offers shorter and cheaper reaction paths for intermediates and the final synthesis of materials, and leads to less toxic waste compared to classical cross-coupling protocols

Summary

Introduction

Π-Conjugated molecules have been often used in organic optoelectronic devices such as organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), organic solar cells (OSCs) and others [1,2]. Direct C–H arylation has been developed as a method for synthesis conjugated materials for use in organic electronics from simple building blocks [15,16,17,18]. This method offers shorter and cheaper reaction paths for intermediates and the final synthesis of materials, and leads to less toxic waste compared to classical cross-coupling protocols. We report the synthesis of 7,7’-(4,4-bis(2-ethylhexyl)-4Hcyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole) by direct C–H cross-coupling of 4,7-dibromobenzo[c][1,2,5]thiadiazole with 4,4-bis(2-ethylhexyl)4H-cyclopenta[2,1-b:3,4-b’]dithiophene.

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Materials and Methods