New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties.

Daria G Selivanova,Georgii G Abashev,Georgii G Abashev,Igor V Lunegov,Alexander N Vasyanin,Olga A Mayorova,Elena V Shklyaeva,Elena V Shklyaeva,Alexei A Gorbunov

doi:10.3762/bjoc.13.158

Daria G Selivanova, Georgii G Abashev + Show 7 more

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https://doi.org/10.3762/bjoc.13.158

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Abstract

In this paper we present a synthetic approach to six new D–π–A–D conjugated chromophores containing the N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment. Such readily functionalizable heterocycle as carbazole was used as a main starting compound for their preparation. The investigation of the optical properties has shown that the positive solvatochromism is inherent to the chromophores containing an electron-withdrawing prop-2-en-1-one fragment, while the compounds containing a 2-aminopyrimidine moiety exhibit both positive and negative solvatochromism. The fluorescence quantum yields were experimentally determined for some of the synthesized chromophores; e.g., 1-(5-arylthiophen-2-yl)ethanones quantum yields were found to lie in an interval of 60–80%. Electrochemical oxidation of the synthesized chromophores has resulted in the formation of colored thin oligomeric films that became possible due to the presence of carbazole or pyrrole fragments with free electron-rich positions.

Highlights

Nowadays a great number of research projects concerning the synthesis of organic conjugated systems with a wide scope of their applications, primarily as materials for organic electronic devices such as light-emitting diodes, field-effect transistors, and electrochromic devices exist
The objective of the presented work involves the design and further synthesis of 4,6-diaryl-substituted 2-(pyrrol-1-yl)pyrimidines, embedding 9-[ω-(4-methoxyphenoxy)alkyl]carbazole moieties as substituents, one of which is directly linked with a central pyrimidine core and another one is linked by a rigid thiophene cycle as a π-conjugated bridge
In this paper we describe a synthetic approach to some new D–π–A–D conjugated systems which include 9-[ω-(4-methoxyphenoxy)alkyl]carbazole as a donor fragment (D) and prop-2enone and pyrimidine units as electron acceptor moieties (A)

Summary

Introduction

Nowadays a great number of research projects concerning the synthesis of organic conjugated systems with a wide scope of their applications, primarily as materials for organic electronic devices such as light-emitting diodes, field-effect transistors, and electrochromic devices exist. Nowadays some new synthetic procedures [3,5,6,7] have given the opportunity to prepare conjugated systems which include 1,8-, 2,7- or 9(3)carbazolylene units The incorporation of such moieties changes the optical and electrochemical properties of the resulted conjugated systems [5]. The optical and electrochemical properties of the prepared compounds were investigated by UV–vis absorption spectroscopy and cyclic voltammetry Electrochemical oxidation of these heterocycles resulted in the formation of thin films on the surface of an ITO working electrode. The morphology of grown films has been investigated by means of scanning tunneling microscopy

Results and Discussion

Conclusion

Organic Electronics for a Better Tomorrow