322 © Published by College of Education for Pure Science (Ibn Al-Haitham), University of Baghdad. This is an open-access article distributed under the terms of the Creative Commons Attribution 4.0 International License Heterocyclic Azo Dyes Derived from Adenine: Synthesis, Spectral Characterization, a wool Dying Zaid Zuhair Abd1* and Alyaa Khider Abbas2 1,2 Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq. *Corresponding Author. Received: 8 February 2023 Accepted: 31 May 2023 Published: 20 July 2024 doi.org/10.30526/37.3.3280 Abstract The novel (La-PAA) of the ligand 8-[3-(pyrazoyl)azo]Adenine (PAA) was synthesized with the molar ratio (1:3), which was appointed by using the mole ratio method. The C.H.N.S elemental analysis, magnetic measurement, thermal analysis, and spectral methods (UV-Vis, FTIR, and HNMR) were employed to support the mode of binding and geometrical structure for ligand (PAA) and (La-PAA) complex. The FTIR and 1H N.M.R. spectral results showed that the (PAA) acts as neutral N, N-bidentate with La (III), as well as the absorption results in specific octahedral structures for (La-PAA) complex. The thermal decomposition of the (PAA) ligand and its (La-PAA) complex performed many steps, and the (La-PAA) complex is more thermal stable than the free ligand. The dyeing performance of the free ligand and (La-PAA) complex was tested, and they have straightforward and bright colors. The photostability of the free ligand (PAA) and [La(PAA)3]Cl3.3H2O complex in ethanol at a concentration of (10-4M) and subjecting them to ultraviolet (U.V.) radiation for two hours at room temperature. Finally, this research aimed to synthesize and characterize the ligand (PAA) and its complex, as well as test the ability of the ligand (PAA) and its complex on wool fiber. Keywords: Azo, dyeing, adenine, spectral study, ligand, complex. 1. Introduction There are two separate kinds of azo compounds, depending on whether the R1 and R2 are alkyl or aryl groups. The word "azo" is derived from the word "azote," a French word for nitrogen [1,2]. The azo dye era began with the development of Bismarck brown and aniline yellow in the 1860s. [3]. Numerous studies on the synthesis, spectral analysis, physical characteristics, and elemental analysis of various azo dye types and their complexes with lanthanide elements, the lanthanide metal complexes, have been published. In azo dye- containing synthesis in both industrial and inorganic chemistry, ligands constitute a crucial topic of study [4]. Since azo dyes' metal complexes have been extensively researched for use in industrial and spectral analytical applications, there has been a significant interest in azo dyes as chelating ligands and their metal complexes in coordination chemistry [5]. https://creativecommons.org/licenses/by/4.0/ https://orcid.org/0009-0007-3743-7395 mailto:zaid93zuhair@gmail.com https://orcid.org/0000-0002-8400-0926 mailto:alyaa.abbas@sc.uobaghdad.edu.iq IHJPAS. 2024, 37( 3 ) 323 As 60–80% of all organic colorants, azo colorants are the most important category of synthetic dyes. They are widely employed in substrates such as plastic, waxes, textile fibers, mineral oils, papers, food products, cosmetic, and molecular memory storage [6]. Assembling a new ligand (PAA) and applying [La (III)] in this investigation. Dying performance for wool was investigated for the ligand (PAA) and La-complex. 2. Materials and Methods In each instance, the best materials and solvents that were available were used. Analyses of the ligand's elements, metal content, and (La-PAA) complex are evaluated utilizing the (C.H.N.S) (Eure EA 3000 Elemental Analyzer). Infrared Fourier Transform of the series spectrophotometry includes (FT-IR) spectrophotometry, which employs this technique. CsI was utilized to record infrared spectra in the (250-4000) cm-1 range using the spectrophotometer SHIMADZU 8400s. In order to record UV-Vis spectra for the ligand and (La-PAA) complex under investigation in the range of (200-1100) nm, a (SHIMADZU 1800 UV-Vis spectrophotometer) was utilized. On a BRUKER AV 400 Avance-III, the 1H-NMR spectra were measured (400 MHz and 100 MHz). The use of thermal analysis (TGA) is to ascertain the amount of metal present in the synthesized ligands and (La-PAA) complex (SDT Q600 V20.9 Build). The melting points of each chemical were calculated using the Gallenkamps melting point instrument. The molar conductance of metal ion complexes in deionized distilled water (10-3 M). A Sherwood scientific auto-magnetic susceptibility balance model was used to test the complex magnetic susceptibility at room temperature. 2.1 Synthesis of azo dyes ligands At first, the diazonium salt was prepared from 3-aminopayrazol (0.83 g; 0.01), which was dissolved in a mixture of 10 mL of distilled water and 10 ml of conc. CH3COOH and diazotized at 5 ℃ with a 10% solution of NaNO2. The solution was then put in an ice bath for 20–30 minutes with stirring. After that, diazonium salt solution was gradually added to (1.351 g; 0.01 mole) of an alkaline alcoholic solution [10%, 12 mL, NaOH in ethanol] adenine. The resultant mixture was neutralized at pH 5–6, as in Scheme 1, and the solution was left to precipitate overnight. This residue was filtrated and washed a number of times with a mixture (1:1) of ethanol and H2O. The color precipitate was subsequently left for during [7]. Scheme 1. Mechanisms of of PAA ligand synthesis. IHJPAS. 2024, 37( 3 ) 324 2.2 Synthesis of La- PAA complex The [La(PAA)3]Cl3.3H2O complex was synthesized in a mole ratio of (M:L) (1:3) by adding (0.693 g; 0.003 mole) of the (PAA) ligand in absolute ethyl alcohol to an aqueous solution of metal ion salt [La (III)] (0.245; 0.001 mole). After 3 hours of refluxing using ethanol: acetone (3:1) as the solvent, the combined solution's outcome was modified using thin layer chromatography (TLC). The colorful precipitate produced was filtered, repeatedly washed with water and ethanol (1:1), and then allowed to dry. 3. Results 3.1 Physicochemical feature The novel is a yellow-colored azo ligand (PAA) with an adenine core, which was sketched in Scheme 1. [La(PAA)3] Cl3.3H2O complex is dark yellow, solid, amorphous in nature, non- hygroscopic, and stable at room temperature, as well as soluble in water, ethanol, methanol, DMSO, etc. The analytical and physical results are displayed in Table 1. The elemental analysis data was found to be in good agreement with the calculated data, and the metal-to-ligand ratio (M:L) is (1:3) stoichiometry. The molar conductance measurement was proposed for the (1:3) electrolytic nature of the complexes in (10-3 M) water, as in Table 1. Table 1. Physicochemical advantage of the synthesized compounds. Comp. (M.wt) (gm/mol) M:L Color λ (nm) % Experimental % (Theoretical) M.P (Cº) Ʌm (S.mol-1 .cm2) PAA(C8H9N9) (231.22) - Brown 322 C H N M Cl 110 - 41.51 (41.87) 3.89 (3.82) 54.49 (54.88) - - [La(PAA)3]Cl3.3H2O (991.57) 1:3 Yellow 334 29.04 (28.45) 3.32 (3.89) 38.12 (37.54) 17.88 18.23 10.45 10.08 360 118.33 3.2 Nature of (La-PAA) The most often used technique for identifying the kind of complexes formed in a solution that requires separation is the mole ratio approach [8], which was utilized to examine the stoichiometric reaction between the ligand (PAA) and the [La(PAA)3] Cl3.3H2O. The absorbance versus molar ratio of the sample was measured using this method (M: L) when the ligand concentration is adjusted to 0.25 mL while the metal ion concentration remains same, this type of figure permits a significant break. This is because the complex was created, and there is no retable dissociation. Currently, this shows the composition of complexes. The outcomes are shown in Figure 1 along with the link between absorbance and (M: L) ratio Table 2 shows the results for [La(PAA)3] Cl3.3H2O are (1:3) (M:L). IHJPAS. 2024, 37( 3 ) 325 Table 2. Absorbance versus mole ratio for (PAA) and (La-PAA) complex solutions at (λ max). M:L Absorbance at λ max (nm) La (PAA) (402) 1:0.25 0.28 1:0.5 0.47 1:0.75 0.48 1:1 0.49 1:1.25 0.502 1:1.5 0.55 1:1.75 0.564 1:2 0.588 1:2.25 0.59 1:2.5 0.61 1:2.75 0.62 1:3 0.632 1:3.25 0.63 1:3.5 0.64 1:3.75 0.65 1:4 0.654 Figure 1. Molar ratio curves for PAA-La ion solutions at λ max and [La(PAA)3]Cl3.3H2O 3.3 Thermogravimetric analysis (TGA) The ligand thermal degradation (PAA) and [La(PAA)3] Cl3.3H2O complex were discussed by TGA in the range (25-800) °C with argon gas. The suggested formula was verified using thermal analysis, which was also used to examine the thermal stability of the synthesized ligand (PAA) with the [La(PAA)3] Cl3.3H2O complex. The results seem to agree with the formula suggested by the analytical data [9]. Figures 2 , 3 and Table 3 explained that the ligand (PAA) was decomposed in three steps, but [La(PAA)3] Cl3.3H2O complexes decomposed in four steps. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.5 1 1.5 2 2.5 3 3.5 4 La(PAA) La(PAA) IHJPAS. 2024, 37( 3 ) 326 There is no mass loss up to 270 °C in the case of the ligand, an indication of a lack of moisture, while in the case of [La(PAA)3] Cl3.3H2O, the decomposition was up to 25–90.5 °C due to lattice water. The residues of (PAA) and [La(PAA)3] Cl3.3H2O were (26.9%) and (34.17%), respectively, which is an indication that the (La-PAA) is more stable than the ligand. Table 3. TGA of ligand (PAA) and [La(PAA)3] Cl3.3H2O complex. Comp. Molecular formula (molecular weight) g/mole Step TG. Range of the decompositi on on (0 Cº) Suggested assignment Calculate % Found % PAA C8H9N9 (231.22) 1 25-270 C4H9N2.75 41.3 42.21 2 270-360 C2 10.37 10.23 3 360-800 C2N1.75 20.97 20.66 Residue <800 Cº N4.5 27.24 26.9 [La(PAA)3]Cl3.3H2O LaC24H33N27Cl3O3 (991.57) 1 (25-90.5) Cº H33O3 8.06 8.04 2 90.5- 196.71 C8N3Cl3 23.80 23.88 3 196.71- 543.95 C8N8 20.67 20.41 4 543.95- 800 C8N2 12.30 13.08 Residue < 800 Cº LaN14 34.17 34.58 Figure 2. Thermogram of PAA ligand. IHJPAS. 2024, 37( 3 ) 327 Figure 3. Thermogram of the [La(PAA)3]Cl3.3H2O complex 3.4 The 1H NMR Spectra of the ligand PAA The HNMR investigation for the free ligand PAA was displayed in Figure 4 (DMSO-d6). A singlet signal is attributed to the δ (NH, H) of the pyrazole moiety at (11.86) ppm and the δ (CH) of the pyrimidine moiety at (3.3 ppm) ppm [10]. The signals at (8.09 and 8.25 ppm) were indicative of δ (-NH2, 2H) in adenine [11], whereas the chemical shift at (8.45 ppm) was traced back to δ (-NH) in the imidazole moiety [12]. The several signals that were seen between (7.00 and 7.9) ppm belonged to the proton of the naphthalene ring [13]. Figure 4. 1HNMR Spectrum for the PAA ligand IHJPAS. 2024, 37( 3 ) 328 3.5 Electronic spectra and magnetic properties The UV-Vis spectra of the free ligand (PAA) in the solvent ethanol [10-4] with extend (200-1100) nm show two bands at 274 nm, 36496.35 cm-1 and 322 nm, 31152.65 cm-1, which were attributed to the (π → π*) transition for intramolecular charge transfer taking place via the azo moiety, as in Figure 5 [14]. Figure 6 shows the electronic spectra of the [La(PAA)3] Cl3.3H2O complex, while the data obtained are included in Table 4. Chelating to the lanthanide ion causes both chromic shifts in the absorption band. Due to the partially filled 4f- orbital, most lanthanide ions absorb electromagnetic energy, particularly in the visible region of the spectrum, which excites the ions from their ground state to a higher electronic state. Electric radiation and magnetic dipoles can both excite f-f transitions. Transitions of the electric dipole are prohibited by parity (Laporte-forbidden) and much weaker than the magnetic dipole transitions, which are often parity-allowed and not visible. These transitions were, therefore, absent from the spectra of the [La(PAA)3] Cl3.3H2O complex because they were fragile and obliterated by the severe band absorption (PAA) [15]. The magnetic properties of the [La(PAA)3] Cl3.3H2O complex are paramagnetic. Table 4. Electronic spectra for the ligand (PAA) and [La(PAA)3]Cl3.3H2O complex. Compound λmax (nm) Absorption band (cm-1) Transition Geometry PAA 274 36496.35 (π → π*) - 321 31152.65 (π → π*) - [La(PAA)3]Cl3.3H2O 402 24875.62 C.T O.h Figure 5. The PAA ligand. IHJPAS. 2024, 37( 3 ) 329 Figure 6. The [La(PAA)3]Cl3.3H2O. 3.6 FT-IR spectra of PAA ligand and [La(PAA)3]Cl3.3H2O complex Azo dye ligands (PAA) and the [La(PAA)3]Cl3.3H2O complex were characterized by FTIR spectra with samples produced as KBr discs. The influential FT-IR vibration bands of the (PAA) ligand and [La(PAA)3]Cl3.3H2O complex are shown in Table 5, which may be used to investigate the coordination between the ligand and [La(PAA)3]Cl3.3H2O complex. Their spectra were captured between (250 and 4000 cm-1), through Figures 7 and 8. 1) The most important band for the azo compound is the azo moiety in the spectrum of the free ligand, which appeared at (1413) cm-1, which was displaced to a higher wavelength at ʋ (1542) cm-1 in the spectra of the [La(PAA)3]Cl3.3H2O complex, showing that the pair of electrons on the nitrogen atom for the azo moiety is in a state of coordination with the metal ion [16]. So, the intensity of this band was reduced with a doublet shape in the spectrum of the [La(PAA)3]Cl3.3H2O complex when compared to the spectrum of a free ligand (PAA) [16]. 2) The FT-IR spectrum of the free ligand (PAA) was allocated to the band with the symbol (N- H), but the spectrum of the complex's symmetric (NH2) moiety remained unchanged in Table 5. The little shift in position or form, which is frequently ascribed to a decrease or rise in resonance as a result of chelating, suggests that this moiety did not chelate [17]. 3) The imine moiety (C=N) for the imidazole ring in adenine was referenced by the ligand (PAA) in a band at (1701-1687) cm-1. As compared to the spectra of the ligand, this band was pushed to its most excellent wavelength in the region of (1745) cm-1 in the [La(PAA)3]Cl3.3H2O complex because of the coordination with the metal ion [18]. 4) The bands were attributed to ʋ (C=N) pyr. and ʋ (C=N) prm has little effect on complexation [19] Table 5 and Figures 7, 8. 5) The spectra of [La(PAA)3]Cl3.3H2O complex were recorded new bands in the (420457) cm- 1 and (615-661) cm-1, respectively, which belong to ʋ (Ln-Nazo) and (Ln-Nimd.) [17]. 6) According to the information above, the ligand (PAA) functions as a neutral N, N-bidentate through the nitrogen atoms in the azo and imidazole moiety of adenine. IHJPAS. 2024, 37( 3 ) 330 Table 5. Vibration bands of the (PAA) ligand and [La(PAA)3]Cl3.3H2O complex. Assessment center ν (N-H) ν (C=N)pyr. ν (C=N)imd ν (C=N)pyrm . ν (N=N)azo ν (M-N)azo ν (M-N)imd. PAA 3355 st. 3431 b,st 1639 sh,m 1701 d,m 1687 d,m 1558 st. 1413 st,sh - - [La(PAA)3]Cl3.3H2O 3404 b,st 3423b , st. 1623sh, m - 1745 1554 st. 1542 m. . 420 w 457 w. 615 w. 661 w. s=strong, m=medium, w=weak, sh=sharp, prm.=Pyrimidine , imd.=Imidazole pyr=Pyrazole. Figure 7. The FTIR spectrum of (PAA) ligand. Figure 8. The FTIR spectrum of [La(PAA)3]Cl3.3H2O complex. 3.7 Wool dying The free ligand (PAA) and [La(PAA)3]Cl3.3H2O complex were tested on wool fiber. Wool fiber is a complicated structure that contains protein filaments, the majority of which are keratin amino groups and carboxyl groups [20]. Numerous polar groups, including -OH, -NH, and -SH groups, are present in wool fiber. In polyamide fiber, there may be an amino group at the end IHJPAS. 2024, 37( 3 ) 331 of the chain as well as a sizable number of -NH groups [21]. The kind of metal and its valence state, washing time (60 min), solution concentration, solution length, pH, temperature (40 Co), and other factors all affect how quickly and how much metal is absorbed. Particularly at alkaline pHs, the nitrogen atoms of amino and amide groups are capable of forming coordination bonds. The hue of the wool textile was in the range of yellow to brown after being dyed with the ligand (PAA) and [La(PAA)3]Cl3.3H2O complex Figure 9. Figure 9. The wool textile dyeing of ligand (PAA) with its metal complexes wash fastness. When soap with a 2% concentration was used to test the textile color fastness for washing, the outcomes were excellent Table 6. According to the Iraqi Standard No. 3610 for wool textiles, the findings were converted to a grayscale, as shown in Table 6. The results of dyeing and different fastness characteristics of the [La(PAA)3]Cl3.3H2O complex and azo ligand (PAA) on wool textile. Table 6. Results of dyeing and various fastness feature of azo ligand (PAA) and [La(PAA)3]Cl3.3H2O complex on wool textile. compound color fastness Staining PAA 4 4 [La(PAA)3]Cl3.3H2O. 4 4 Grading:5-4 (good), 3(moderate), 1-2(not good) 3.8 Photo stability By soaking the ligand (PAA) and [La(PAA)3]Cl3.3H2O complex in ethanol at a concentration of (10-4M) and subjecting them to ultraviolet (UV) radiation for two hours at room temperature, their photostability was examined, as in Table 7. The photostability % was calculated [22] using the difference between the initial absorbance (i.e., before irradiation and the final absorbance, to the beginning absorbance). The following findings were obtained from the photostability test: (PAA)> [La(PAA)3]Cl3.3H2O. IHJPAS. 2024, 37( 3 ) 332 Table 7. Photo degradation details of ligands and [La(PAA)3]Cl3.3H2O under irradiation (𝝀 =256 nm). Compound Time (min) Abs (nm) Photo stability percentage PAA 0 1.955 6.08% 10 1.845 20 1.934 30 1.994 40 1.91 50 1.973 60 1.977 75 1.934 90 1.922 105 1.925 120 1.836 [La(PAA)3]Cl3.3H2O 0 1.897 3.42% 10 1.985 20 1.942 30 1.933 40 1.955 50 1.99 60 1.962 75 1.944 90 1.952 105 1.988 120 1.962 5. Conclusion Following spectral and analytical physicochemical studies on the ligand (PAA) and [La(PAA)3]Cl3.3H2O, certain conclusions have been drawn that establish the following points: The ligand (PAA), which acted as a neutral N, N-bidentate chelating ligand that bonded to La (III), produced an octahedral chelating complex through the nitrogen atoms of imidazole in adenine and with a nitrogen atom in the azo moiety. Acknowledgment The authors thank the Department of Chemistry, College of Science, University of Baghdad for research approval. 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