Monoazo Dyes: Coupling Reactions between Indanone Compounds and Heterocyclic Aminothiophene-Containing Spiro Group

Year 2024, Volume: 1 Issue: 1, 1 - 7, 31.07.2024

Naki Çolak , Gülnihal Erten , Aynur İzancı , Umut Sancur

Abstract

In this study, firstly, 2-amino-spiro[benzo]thiophene derivatives were prepared using the Gewald method. Subsequently, monoazo dyes were synthesized using conventional diazotization method, with 2-indanone or 1,3-indandione compounds as preferred coupling components. The chemical structures of the monoazo dyes have been characterized using several spectroscopic methods (FT-IR, 1H-NMR, 13C-APT NMR). The tautomeric forms of the dyes were discussed, and it was concluded that the hydrazo form is the dominant tautomer.

Keywords

2-Aminothiophene, Spiro[benzo]thiophene, Azo dyes, Heterocyclic components

Ethical Statement

It is declared that scientific and ethical principles have been followed while carrying out and writing this study and that all the sources used have been properly cited.

Supporting Institution

TÜBİTAK

Project Number

1919B012224050

Thanks

This work was supported by TUBITAK through a research Grant No. 1919B012224050.

References

• Christie RM. Colour Chemistry. 2nd ed. Cambridge: The Royal Society of Chemistry; 2015. Chapter 3, Azo Dyes and Pigments; p. 72-98.
• Mishra VR, Ghanovatkar CN, Sekar N. UV protective heterocyclic disperse azo dyes: Spectral properties, dyeing, potent antibacterial activity on dyed fabric and comparative computational study. Spectrochim Acta A: Mol Biomol Spectrosc. 2019;223:117353. doi:10.1016/j.saa.2019.117353
• Mohammadi A, Khalili B, Tahavar M. Novel push-pull heterocyclic azo disperse dyes containing piperazine moiety: Synthesis, spectral properties, antioxidant activity and dyeing performance on polyester fibers. Spectrochim Acta A: Mol Biomol Spectrosc. 2015;150:799-805. doi:10.1016/j.saa.2015.06.024
• Manjunatha B, Bodke YD, Nagaraja O, Lohith TN, Nagaraju G, Sridhar MA. Coumarin-Benzothiazole based azo dyes: Synthesis, characterization, computational, photophysical and biological studies. J Mol Struct. 2021;1246:131170. doi: 10.1016/j.molstruc.2021.131170
• Sujamol MS, Athira CJ, Sindhu Y, Mohanan K. Synthesis, spectroscopic characterization, dyeing performance and corrosion inhibition study of transition metal complexes of a novel azo derivative formed from 2-aminothiophene. Chem Data Coll. 2021;31:100634. doi: 10.1016/j.cdc.2020.100634
• Karcı F, Bakan E. New disazo pyrazole disperse dyes: synthesis, spectroscopic studies and tautomeric structures. J Mol Liq. 2015;206:309-315. doi: 10.1016/j.molliq.2015.02.032
• Khedr AM, El-Ghamry H, Kassem MA, Saad FA, El-Guesmi N. Novel series of nanosized mono- and homobi-nuclear metal complexes of sulfathiazole azo dye ligand: Synthesis, characterization, DNA-binding affinity and anticancer activity. Inorg Chem Commun. 2019;108:107496. doi:10.1016/j.inoche.2019.107496
• Mughal EU, Raja QA, Alzahrani AYA, Naeem N, Sadiq A, Bozkurt E. Pyrimidine-based azo dyes: Synthesis, photophysical investigations, solvatochromism explorations and anti-bacteral activity. Dyes Pigm. 2023;220:111762. doi:10.1016/j.dyepig.2023.111762
• Yıldırım F, Demirçalı A, Karcı F, Bayrakdar A, Taşlı PT, Kart, HH. New coumarin-based disperse disazo dyes: synthesis, spectroscopic properties and theoretical calculations. J Mol Liq. 2016;223:557-565. doi:10.1016/j.molliq.2016.08.008
• Karabacak Ç, Dilek Ö. Synthesis, solvatochromic properties and theoretical calculation of some novel disazo indole deys. J Mol Liq. 2014;199:227-236. doi:10.1016/j.molliq.2014.09.019
• Harisha S, Keshavayya J, Kumara Swamsy BE, Viswanath CC. Synthesis, characterization and electrochemical studies of azo dyes derived from barbituric acid. Dyes Pigm. 2017 Jan;136:742-753. doi:10.1016/j.dyepig.2016.09.004
• Erten G, Karcı F, Demirçalı A, Söyleyici S. 1H-pyrazole-azomethine based novel diazo derivative chemosensor for the detection of Ni2+. J Mol Struct. 2020 Apr 15;1206:127713. doi:10.1016/j.molstruc.2020.127713
• Derkowksa-Zielinska B, Skowronski L, Biitseva A, Grabowski A, Naparty MK, Smokal V, Kysil A, Krupka O. Optical characterization of heterocyclic azo dyes containing polymers thin films. Appl Surf Sci. 2017;421(B):361-366. doi: 10.1016/j.apsusc.2016.12.080
• Ayare NN, Sharma S, Sonigara KK, Prasad J, Soni SS, Sekar N. Synthesis and computational study of coumarin thiophene-based-π-A azo bridge colorants for DSSC and NLOphoric application. J Photochem Photobiol A. 2020;394:112466. doi: 10.1016/j.jphotochem.2020.112466
• Karabulut YK, Gürkan YY. Investigation of some azo dyes by QSAR method and acute toxicity test with Daphnia Magna. J Ins Sci Tech. 2023;13(2):1110-1119. doi:10.21597/jist.1214772
• Karcı F, Karcı F. Synthesis and tautomeric structures of some novel thiophene-based bis-heterocyclic monoazo dyes. J Mol Struct. 2012;1024:117-122. doi: 10.1016/j.molstruc.2012.05.021
• Singh MV, Tiwari AK, Sharma YK, Chauhan MS, Sethi M, Guo Z. Synthetic procedures, properties, and applications of thiophene-based azo scaffolds. ES Food Agrofor. 2023;12:887. doi: 10.30919/esfaf887
• Abdou MM. Thiophene-based azo dyes and their applications in dyes chemistry. Am.J. Chem. 2013;3(5):126-135. doi:10.5923/j.chemistry.20130305.02
• Nassar HS. New azo disperse dyes with thiophene moiety for dyeing polyester fibers. Int. J. Text. Sci. 2015;4(5):102-112. doi: 10.5923/j.textile.20150405.02
• Sharma SJ, Khan ZN, Zambare AA, Bagal MS, Barshi AS, Rindle SM, Sekar N. Synthesis, spectroscopic, DFT, TD-DFT, and dyeing studies of 2-amino-3-cyano thiophene-based azo dyes on wool and nylon. Dyes Pigm. 2024;228:112209. doi: 10.1016/j.dyepig.2024.112209
• Mezgebe K, Mulugeta E. Synthesis and pharmacological activities of azo dye derivatives incorporating heterocyclic scaffolds: a rewiev. RSC Adv. 2022;12(40):25932-25946. doi: 10.1039%2Fd2ra04934a
• Gouda MA, Eldien HF, Girges MM, Berghot MA. Synthesis and antitumor evaluation of thiophene based azo dyes incorporating pyrazolone moiety. J. Saudi Chem. Soc. 2016;20(2):151-157. doi:10.1016/j.jscs.2012.06.004
• Al-Azmi A, John E. Synthesis of 4-arylazo-2-(N-pyrazolylcarboxamido)thiophene disperse dyes for dyeing of polyester and their antibacterial evaluation. Text. Res. J. 2020;90(23-24):1-11. doi: 10.1177/0040517520931476
• Ayare NN, Sharma S, Sonigara KK, Prasad J, Soni SS, Sekar N. Synthesis and computational study of coumarin thiophene-based D-π-A azo bridge colorants for DSSC and NLOphoric application. J. Photochem. Photobiol. A Chem. 2020;394:112466. doi: 10.1016/j.jphotochem.2020.112466
• Sharma SJ, Sekar N. Exploration of 4-substituted thiophene-based azo dyes for dye-senditized solar cells and non-linear optical materials: synthesis and an in silico approach. Phys. Chem. Chem. Phys. 2024; Advance article. doi: 10.1039/D4CP00918E
• El-Haddad MN, Fouda AS, Mostafa HA. Corrosion inhibition of carbon steel by new thiophene azo dye derivatives in acidic solution. J. Materi. Eng. Perform. 2013; 22:2277-2287. doi: 10.1007/s11665-013-0508-0
• Gadow HS, Fawzy A, Khairy M, Sanad MMS, Toghan A. Experimental and theoretical approaches to the inhibition of carbon steel corrosion by thiophene derivative in 1 M HCl. Int. J. Electrochem. Sci. 2023;18(7):100174. doi: 10.1016/j.ijoes.2023.100174
• Peet NP, Sunder S, Barbuch RJ, Vinogradoff AP. Mechanistic observations in the Gewald syntheses of 2-aminothiophenes. J Heterocycl Chem. 1986;23(1):129–134. doi: 10.1002/jhet.5570230126
• Gewald K. Methods for the synthesis of 2-aminothiophenes and their reactions (review). Chem Hetrocycl Compd. 1976;12:1077-1090. doi: 10.1007/BF00945583
• Gewald K, Schinke E, Bottcher H. Heterocyclen aus CH-aciden Nitrilen, VIII. 2-Amino-thiophene aus methylenaktiven Nitrilen, Carbonylverbindungen und Schwefel. Chem Ber. 1966;99(1): 94-100. doi: 10.1002/cber.19660990116
• Buldurun K, Turan N, Savci A, Alan Y, Colak N. Synthesis, characterization, X-ray diffraction analysis of a tridentate Schiff base ligand and its complexes with Co (II), Fe (II), Pd (II) and Ru (II): Bioactivity studies. Iran J Chem Chem. Eng. 2022;41(8):2635-2649. doi: 10.30492/ijcce.2021.531629.4775
• Çolak N, Gündüzalp AB, Mamaş S, Akkaya D, Kaya K. Synthesis, spectroscopic studies and electrochemical properties of Schiff bases derived from 5-chloro-2-hydroxybenzaldehyde with methyl 2-amino-6-methyl-4, 5, 6, 7-tetrahydrobenzo [b] thiophene-3-carboxylate. Bulg Chem Commun. 2016;48(Special C):20-26.
• Çolak N, Altıner S, Şahin ZS, Gündüzalp AB. Synthesis, Spectroscopic and Computational Studies of (E)-2-(2,3-dihydroxy)-benzylidene)amino)-6-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile. Gazi University Journal of Science. 2017;30(3):245 – 254.
• Maradiya HR. Synthesis of azobenzo[b]thiophene derivatives and their dyeing performance on polyester fibre. Turk J Chem. 2001;25(4):441-450.