European Journal of Chemistry

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

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Published: Dec 31, 2020
DOI: https://doi.org/10.5155/eurjchem.11.4.298-303.2032
Keywords:
Dyes, Alkylations, Azobenzene, Bromohexyl unit, Carboxylic acids, Photo-regulation
Section
Research Article
Issue
Vol. 11 No. 4 (2020): December 2020
Dates
Received 2020-08-21
Accepted 2020-10-03
Published 2020-12-31
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Alina Madalina Darabut
Department of Surface and Plasma Science, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague, 18000, Czech Republic
http://orcid.org/0000-0002-1595-6094
Olha Hennadiivna Purikova
Institute of Macromolecular Chemistry, National Academy of Sciences of Ukraine, Kharkivske shosse 48, Kyiv, 02160, Ukraine
http://orcid.org/0000-0002-4606-8815
Yevheniia Volodymyrivna Lobko
Department of Surface and Plasma Science, Faculty of Mathematics and Physics, Charles University, V Holešovičkách 2, Prague, 18000, Czech Republic
http://orcid.org/0000-0003-1796-7691

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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Darabut, A. M.; Purikova, O. H.; Lobko, Y. V. Synthesis of Bis-Azobenzene Derivatives With Reactive Bromohexyl Unit and Carboxylic Acid Group Based on Disperse Yellow 7. Eur. J. Chem. 2020, 11, 298-303.

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References

[1]. Merino, E. Chem. Soc. Rev. 2011, 40, 3835-3853.
https://doi.org/10.1039/c0cs00183j

[2]. Beharry, A. A.; Woolley, G. A. Chem. Soc. Rev. 2011, 40, 4422-4437.
https://doi.org/10.1039/c1cs15023e

[3]. Fihey, A.; Perrier, A.; Browne, W. R.; Jacquemin, D. Chem. Soc. Rev. 2015, 44, 3719-3759.
https://doi.org/10.1039/C5CS00137D

[4]. Lu, X.; Guo, S.; Tong, X.; Xia, H.; Zhao, Y. Adv. Mater. 2017, 29, 1606467.
https://doi.org/10.1002/adma.201606467

[5]. Imen, H.; Xiaonan, S.; Denis, F.; Frederic, L.; Jean-Christophe, L. Nanoscale 2019, 11, 23042-23048.
https://doi.org/10.1039/C9NR06350A

[6]. Bandara, H. D.; Burdette, S. C. Chem. Soc. Rev. 2012, 41, 1809-1825.
https://doi.org/10.1039/C1CS15179G

[7]. Sin, S. L.; Gan, L. H.; Hu, X.; Tam, K. C.; Gan, Y. Y. Macromolecules 2005, 38, 3943-3948.
https://doi.org/10.1021/ma050097f

[8]. Mahimwalla, Z.; Yager, K. G.; Mamiya, J. I.; Shishido, A.; Priimagi, A.; Barrett, C. J. Polym. Bull. 2012, 69, 967-1006.
https://doi.org/10.1007/s00289-012-0792-0

[9]. Barrett, C. J.; Mamiya, J. I.; Yager, K. G.; Ikeda, T. Soft Matter. 2007, 3, 1249-1261.
https://doi.org/10.1039/b705619b

[10]. Ferri, V.; Elbing, M.; Pace, G.; Dickey, M. D.; Zharnikov, M.; Samorì, P.; Mayor, M.; Rampi, M. A. Angew. Chem. Int Edit. 2008, 47, 3407-3409.
https://doi.org/10.1002/anie.200705339

[11]. Oscurato, S. L.; Salvatore, M.; Maddalena, P.; Ambrosio, A. Nanophotonics-Berlin 2018, 7, 1387-1422.
https://doi.org/10.1515/nanoph-2018-0040

[12]. Sun, S.; Liang, S.; Xu, W. C.; Xu, G.; Wu, S. Polym. Chem. UK 2019, 10, 4389-4401.
https://doi.org/10.1039/C9PY00793H

[13]. Cisnetti, F.; Ballardini, R.; Credi, A.; Gandolfi, M. T.; Masiero, S.; Negri, F.; Pieraccini, S.; Spada, G. P. Chem. Eur. J. 2004, 10, 2011-2021.
https://doi.org/10.1002/chem.200305590

[14]. Homocianu, M.; Serbezeanu, D.; Carja, I. D.; Macsim, A. M.; Vlad-Bubulac, T.; Airinei, A. RSC Adv. 2016, 6, 49980-49987.
https://doi.org/10.1039/C6RA07803F

[15]. Sheng, C.; Norwood, R. A.; Wang, J.; Thomas, J.; Wu, Y.; Zheng, Z.; Tabirian, N.; Steeves, D. M.; Kimball, B. R.; Peyghambarian, N. Appl. Optics 2008, 47, 5074-5077.
https://doi.org/10.1364/AO.47.005074

[16]. Vapaavuori, J.; Bazuin, C. G.; Priimagi, A. J. Mater. Chem. C 2018, 6, 2168-2188.
https://doi.org/10.1039/C7TC05005D

[17]. Barrio, J.; Sanchez-Somolinos, C. Adv. Opt. Mater. 2019, 7, 1900598.
https://doi.org/10.1002/adom.201900598

[18]. Dudziec, B.; Zak, P.; Marciniec, B. Polymers-Basel 2019, 11, 504.
https://doi.org/10.3390/polym11030504

[19]. Vapaavuori, J.; Goulet-Hanssens, A.; Heikkinen, I. T.; Barrett, C. J.; Priimagi, A. Chem. Mater. 2014, 26, 5089-5096.
https://doi.org/10.1021/cm5023129

[20]. Koskela, J. E.; Vapaavuori, J.; Hautala, J.; Priimagi, A.; Faul, C. F.; Kaivola, M.; Ras, R. H. J. Phys. Chem. C 2012, 116, 2363-2370.
https://doi.org/10.1021/jp210706n

[21]. Slavov, C.; Yang, C.; Schweighauser, L.; Boumrifak, C.; Dreuw, A.; Wegner, H. A.; Wachtveitl, J. Phys. Chem. Chem. Phys. 2016, 18, 14795-14804.
https://doi.org/10.1039/C6CP00603E

[22]. Salisu, A. A.; Ab Rahman, M. Z.; Silong, S.; Lutfor, M. R.; Ahmad, M. B. Liq. Cryst. 2011, 38, 423-431.
https://doi.org/10.1080/02678292.2010.550141

[23]. Samanta, S.; Woolley, G. A. ChemBioChem 2011, 12, 1712-1723.
https://doi.org/10.1002/cbic.201100204

[24]. Zhang, Y.; Pei, S.; Wang, Y.; Cui, Z.; Li, N.; Zhu, Y.; Zhang, H.; Jiang, Z. Dyes Pigments 2013, 99, 1117-1123.
https://doi.org/10.1016/j.dyepig.2013.08.004

[25]. Tkachenko, I. M.; Kobzar, Ya. L.; Purikova, O. G.; Tolstov, A. L.; Shekera, O. V.; Shevchenko, V. V. Tetrahedron Lett. 2016, 57, 5505-5510.
https://doi.org/10.1016/j.tetlet.2016.10.101

[26]. Galanti, A.; Santoro, J.; Mannancherry, R.; Duez, Q.; Diez-Cabanes, V.; Valassek, M.; De Winter, J.; Cornil, J.; Gerbaux, P.; Mayor, M.; Samori, P. J. Am. Chem. Soc. 2019, 141, 9273-9283.
https://doi.org/10.1021/jacs.9b02544

[27]. Tecilla, P.; Bonifazi, D. ChemistryOpen 2020, 9, 5291.
https://doi.org/10.1002/open.202000045

[28]. Baek, J. B.; Chien, L. C. J. Polym. Sci. Polym. Chem. 2004, 42, 3587-3603.
https://doi.org/10.1002/pola.20163

[29]. Wal, S.; Kuil, J.; Valentijn, A. R. P. M.; Leeuwen, F. W. B. Dyes Pigments 2016, 132, 7-19.
https://doi.org/10.1016/j.dyepig.2016.03.054

[30]. Tkachenko, I. M.; Belov, N. A.; Kobzar, Ya. L.; Dorokhin, A. V.; Shekera, O. V.; Shantarovich, V. P.; Bekeshev V. G.; Shevchenko, V. V. J. Fluorine Chem. 2017, 195, 1-12.
https://doi.org/10.1016/j.jfluchem.2017.01.008

[31]. Yazici, A.; Dalbul, N.; Salih, B. J. Chem. Soc. Pakistan 2014, 36, 707-711.

[32]. Abdulla, H. A.; Minor, E. C.; Dias, R. F.; Hatcher, P. G. Geochim. Cosmochim. Acta 2010, 74, 3815-3838.
https://doi.org/10.1016/j.gca.2010.04.006

[33]. Ledin, P. A.; Tkachenko, I. M.; Xu, W.; Choi, I.; Shevchenko, V. V.; Tsukruk, V. V. Langmuir 2014, 30, 8856-8865.
https://doi.org/10.1021/la501930e

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