Tert-Butyl Bis(4′-(Hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate

Timofey N Chmovzh,Oleg A Rakitin

doi:10.3390/m1247

Timofey N Chmovzh, Oleg A Rakitin

Open Access

https://doi.org/10.3390/m1247

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Abstract

New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki cross-coupling reaction of tert-butyl bis(4-bromophenyl)carbamate and (4-(hexyloxy)phenyl)boronic acid in the presence of tetrakis(triphenylphosphine)palladium(0). The structure of newly synthesized compounds was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, IR and UV spectroscopy and mass-spectrometry.

Highlights

Over the past ten years, small molecules used in photovoltaic devices have evolved from the simplest ones with the structure of D-A, D-π-A, D-A-D, or A-D-A, to more complex ones containing several different donor and acceptor fragments
Synthesis of new effective donor blocks (D), the use of which in various combinations with acceptors and π-bridges will lead to the production of new photovoltaic materials, i.e., organic solar cells (OSCs), organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), and others, is of great interest [2,3,4,5,6,7]
We report the synthesis of bis(40 -(hexyloxy)-[1,10 -biphenyl]-4-yl)amine 2 via its carbamate derivative

Summary

Introduction

Over the past ten years, small molecules used in photovoltaic devices have evolved from the simplest ones with the structure of D-A, D-π-A, D-A-D, or A-D-A, to more complex ones containing several different donor and acceptor fragments (for example, D-A1-π-A2, A-π-D-π-A). The donor fragment plays a significant role in the formation of the properties of small molecules, as well as polymeric materials. Synthesis of new effective donor blocks (D), the use of which in various combinations with acceptors and π-bridges will lead to the production of new photovoltaic materials, i.e., organic solar cells (OSCs), organic light emitting diodes (OLEDs), organic field effect transistors (OFETs), and others, is of great interest [2,3,4,5,6,7]. We report the synthesis of bis(40 -(hexyloxy)-[1,10 -biphenyl]-4-yl)amine 2 via its carbamate derivative

Results and Discussion

Reaction of tert-butyl bis

Materials and Methods