European Journal of Chemistry 2020, 11(4), 298-303 | doi: https://doi.org/10.5155/eurjchem.11.4.298-303.2032 | Get rights and content

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Synthesis of bis-azobenzene derivatives with reactive bromohexyl unit and carboxylic acid group based on Disperse Yellow 7


Alina Madalina Darabut (1) orcid , Olha Hennadiivna Purikova (2) orcid , Yevheniia Volodymyrivna Lobko (3,*) orcid

(1) Department of Surface and Plasma Science, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague, 18000, Czech Republic
(2) Institute of Macromolecular Chemistry, National Academy of Sciences of Ukraine, Kharkivske shosse 48, Kyiv, 02160, Ukraine
(3) Department of Surface and Plasma Science, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague, 18000, Czech Republic
(*) Corresponding Author

Received: 21 Aug 2020 | Revised: 02 Oct 2020 | Accepted: 03 Oct 2020 | Published: 31 Dec 2020 | Issue Date: December 2020

Abstract


In this work, two types of azobenzene derivatives based on Disperse Yellow 7 (DY7, 4-[4-(phenylazo)phenylazo]-o-cresol) were synthesized, which are bis-azobenzenes bearing flexible functional 6-bromohexyl chain or carboxylic acid moiety. The first one was synthesized by alkylation of DY7 with an excess of 1,6-dibromohexane in the presence of a mild base (K2CO3). The second one (azo dye with carboxylic acid functionality) was obtained by the alkaline hydrolysis of the ester bond of the newly obtained DY7 derivative with the ethoxycarbonyl group. The synthesized compounds were characterized by different spectral analytical techniques such as 1H NMR, 13C NMR, FT-IR, and UV-Vis. They can be employed for the synthesis of a wide variety of azo-based materials, which may be suitable for photochromic systems and molecular electronics applications.


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Keywords


Dyes; Alkylations; Azobenzene; Bromohexyl unit; Carboxylic acids; Photo-regulation

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DOI: 10.5155/eurjchem.11.4.298-303.2032

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Citations

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[1]. Şeyda YALÇIN, Barış SEZGİN, Tahir TİLKİ
Hidroksi Benzoik Asit Sübstitüeli Disazo Boyarmaddelerin Sentezi, Karakterizasyonu ve Absorpsiyon Özelliklerinin İncelenmesi
Deu Muhendislik Fakultesi Fen ve Muhendislik  24(71), 383, 2022
DOI: 10.21205/deufmd.2022247105
/


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How to cite


Darabut, A.; Purikova, O.; Lobko, Y. Eur. J. Chem. 2020, 11(4), 298-303. doi:10.5155/eurjchem.11.4.298-303.2032
Darabut, A.; Purikova, O.; Lobko, Y. Synthesis of bis-azobenzene derivatives with reactive bromohexyl unit and carboxylic acid group based on Disperse Yellow 7. Eur. J. Chem. 2020, 11(4), 298-303. doi:10.5155/eurjchem.11.4.298-303.2032
Darabut, A., Purikova, O., & Lobko, Y. (2020). Synthesis of bis-azobenzene derivatives with reactive bromohexyl unit and carboxylic acid group based on Disperse Yellow 7. European Journal of Chemistry, 11(4), 298-303. doi:10.5155/eurjchem.11.4.298-303.2032
Darabut, Alina, Olha Hennadiivna Purikova, & Yevheniia Volodymyrivna Lobko. "Synthesis of bis-azobenzene derivatives with reactive bromohexyl unit and carboxylic acid group based on Disperse Yellow 7." European Journal of Chemistry [Online], 11.4 (2020): 298-303. Web. 26 Nov. 2022
Darabut, Alina, Purikova, Olha, AND Lobko, Yevheniia. "Synthesis of bis-azobenzene derivatives with reactive bromohexyl unit and carboxylic acid group based on Disperse Yellow 7" European Journal of Chemistry [Online], Volume 11 Number 4 (31 December 2020)

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