congo red spectroscopic studies.pdf

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Cyclic Voltammetric and Ultrasonic Technique on disodium 4-amino-3-[(E) -2-(4-{4-[(E) -2-(1-amino-4sulfonatonaphthalen-2-Yl) diazen-1-Yl] phenyl} phenyl) diazen-1-Yl] naphthalene-1-sulfonate dye with Cu (II), Ni (II), Zn (II) and Pb (II) complexes Jayandran. M Department of Chemistry, Center of Research, Mahendra Engineering College, Namakkal Tamilnadu, India [email protected]

ABSTRACT The organic dye has synthesized between disodium 4-amino-3-[(E)-2-(4-{4-[(E)-2-(1-amino4-sulfonatonaphthalen-2-Yl) reacted with Diazen-1-Yl] phenyl} phenyl)diazen-1-Yl] and naphthalene1-sulfonate disodium and formed 4-amino-3-[(E) -2-(4-{4-[(E) -2-(1-amino-4-sulfonatonaphthalen-2Yl) diazen-1-Yl] phenyl} phenyl) diazen-1-Yl] naphthalene-1-sulfonate. The compound was crystallized by a solution method with slow evaporation technique. The newly synthesized ligand crystal was complexes with Cu (II), Ni (II), Zn (II) and Pb (II) metals. The chemical degradation of the dye was observed spectrophotometric methods, Ultrasonic and Cyclic voltammetric technique.The results reveal the successful formation of crystallization of these dyes could culminate in good complex formation with transition metals and degradation processes, this part of the work was attempted and successfully implemented.

KEYWORDS Congo red, complexes, FTIR, UV, Ultrasonic, Cyclic voltammetric technique and degradation techiques.

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1. INTRODUCTION Dyes are widely used in the textile industry. They are many sources of colored organics emanating as a waste from the textile dyeing process. The dye compound disodium 4amino-3-[(E)-2-(4-{4-[(E)-2-(1-amino-4-sulfonatonaphthalen2-Yl) diazen-1-Yl] phenyl} phenyl) diazen-1-Yl] naphthalene1-sulfonate reported the details of the crystal structure and it is observed from the various properties of crystal report. Hence the aim of this paper is to report the crystal growth, metal complexes, degradation techniques, electro and spectroscopic studies of Congo-Red for the first time. The modern techniques of the present Technical studies, namely ultrasonic technique for the adiabatic compressibility study have become a powerful tool for studying the molecular behavior of liquid mixtures [13]. This is because of its ability of characterizing physicchemical behavior of liquid medium [4, 5] .The another technical measurement of the ultrasonic velocity has been adequately

employed

in

understanding

the

molecular

interactions in the liquid mixtures. Molecular interaction

Figure-1: Metal complexes of Disodium 4-Amino-3-[(E)-2-(4{4-[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl)

Diazen-1-

Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (M= Cu, Ni, Pb and Zn)

2.1.

Fourier

Transforms

Infrared

(Ftir)

studies can be carried out by spectroscopic [6-8] and non-

Spectroscopy

spectroscopic [9, 10] techniques. However, ultrasonic velocity

The FTIR spectra of the dyes and metallo dyes were recorded

[11, 12] measurements have been widely used in the field of

in the 400-4000cm-1 range on a Perkin Elmer FTIR on KBr

interactions and spectral aspect evaluation studies [13, 14].

disc.FTIR spectra of dyes and metallo dyes were recorded

In this present investigation the electrochemical

using KBR pellet (Table 1).IR spectra of the ligand show a

behavior of Cu(II), Ni(II), Zn(II) and Pb(II) complexes of

broad at 3936 cm-1due to the OH groups (Figure-2). In the

disodium

4-amino-3-[(E)-2-(4-{4-[(E)-2-(1-amino-4-

metal complexes, this broad band is still broad due to other

sulfonatonaphthalen-2-Yl)diazen-1-Yl] phenyl}phenyl)diazen-

groups. The stretching vibration of the phenothiazine γ (C=N)

1-Yl] naphthalene-1-sulfonate (Congo red) compound was

is observed in the form of an intense band at 1576 cm-1 in the

technically investigated by Ultrasonic and Cyclic voltammetric

free ligand. The involvement of the deprotonated γ (C-N)

technique. Therefore, in this present investigation the

napthalein-1-ol (Disodium 4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1-

degradation, spectrometrics and electrochemical studies of this

Amino-4-Sulfonatonaphthalen-2-Yl)

dye with metal complexes work have never been reported else

Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate and the spectra

where.

region at 1650 cm-1 is complicated because of the stretching

2. Structural analysis of dyes and its metal complexes: Since the structure of the metal complexes

Diazen-1-Yl]

Phenyl}

modes of –C=C and –N=N- which are superimposed in the same region. However, the band appearing at 1570 cm-1 for Disodium

4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1-Amino-4-

Sulfonatonaphthalen-2-Yl)

Diazen-1-Yl]

Phenyl}

Phenyl)

has been obtained, we characterized the complexes

Diazen-1-Yl] Naphthalene-1-Sulfonate

and determined its possible structure by various

Table 1: Selected IR data (4000-400 cm-1) of Disodium 4-

technical analyses. The suggested structure of the

Amino-3-[(E)-2-(4-{4-[(E)-2-(1-Amino-4-

complexes is shown in Figure-1.

Sulfonatonaphthalen-2-Yl) Diazen-1-Yl] Phenyl} Phenyl)


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Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo red) and its

Compound

Maximum wavelength (nm)

metal complexes

Congo Red

217,311,613

Lead complex of Congo Red

238,329,477

Cobalt complex of Congo Red

239,310,483

Nickel

complex of Congo

Red Copper complex of Congo Red Table:2 -

212,331,620

224,350,

Electronic of Disodium 4-Amino-3-[(E)-2-(4-{4-

[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl) Phenyl}

Phenyl)

Diazen-1-Yl]

Diazen-1-Yl]

Naphthalene-1-Sulfonate

(Congo Red) and its metal complexes.

Figure-3. UV spectral data of Disodium 4-Amino-3-[(E)-2-(4{4-[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl)

Diazen-1-

Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate Figure-2: IR spectral data of 4-amino-3,6-bis[[4-[[4-chloro-6-

(Congo Red) and its complexes.

[(3-sulfophenyl)amino]-1,3,5-triazin-yl]amino]-2-

2.3 ULTRASONIC STUDIES OF DYES

sulfophenyl]azo]-5-hydroxy-2,7-naphthalenedisulfonic

acid

hexasodium compound and its complexes.

2.2. ULTRAVIOLET-VISIBLE SPECTRA The electronic spectra for dyes and its complexes recorded in EtOH are given in the Table 2. The electronic spectral date shows three bands in the region 218-258 nm (Figure-3). When compared with the pure ligand spectrum, a shift in the bands is noticed, due to the formation of the complexes. A peak or shoulder in the region 260-475 nm can be assigned to the nitrogen (imino) to lead, Zinc, nickel and copper transitions. The band at 288 nm corresponds to n-π * and the one at 217-224 nm to π -π * transitions. A broad band around 680 nm is assigned to a d-d transition in the metal complexes (15-17).

The present work deals with ultrasonic velocity and density measurements of solutions of Disodium-4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1-Amino-4Sulfonatonaphthalen-2-Yl)

Diazen-1-Yl]

Phenyl}

Phenyl)

Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo red) Salt) and its metal (II) complexes at various concentrations by keeping temperature constant. The dependence of these parameters is found to be useful in understanding the nature and extent of interaction between molecules. The Acoustical parameters of dyes and its metal (II) complexes are shown in Table 3-7 and Figure 4-8. I can be seen that the average values of ultrasonic velocity may be increases and average values of adiabatic compressibility factor may be decreases in all the pH solution, non-linearly with 46 | IJBRITISH

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increasing concentration of dyes. This can be explained by

2-(1-Amino-4-Sulfonatonaphthalen-2-Yl)Diazen-1-Yl]Phenyl}

resorting to flickering cluster model of water. When the dye is

Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) at

dissolved in water, the dye molecules would first disrupt the

303K

open structure organization leaving the molecules in closely fitted helical cavities. The dye molecules can occupy both the nodes and voids of the water framework. Such an increase in close packed structures of water result in increased cohesion of water molecules leading to decrease in compressibility. This also results in may be increase of ultrasonic velocity. However, the adiabatic compressibility (β ), intermolecular free length (Lf) and acoustic impedance (Z) may be decrease with increase of concentration at constant temperature. The ultrasonic velocity of metal dye complex is higher than dye of same concentration. The may be increase in velocity and may be decrease of free length may be due to strong solute-solute-solvent interaction [18-21]. In all the metal-dye complexes, the adiabatic

Table 5: Ultrasonic velocity and related acoustical parameters

compressibility factor (β ) is may be less than the

in the solution of Zinc-Disodium-4-Amino-3-[(E)-2-(4-{4-[(E)-

corresponding dyes of similar concentration. These suggest

2-(1-Amino-4-Sulfonatonaphthalen-2-Yl)Diazen-1-Yl]Phenyl}

that salvation of dye complex may be increases which is

Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) at

indicated by the may be decrease of adiabatic compressibility

303K

factor. Table 3: Ultrasonic velocity and related acoustical parameters in the solution of Disodium -4-Amino-3-[(E)-2-(4-{4-[(E)-2(1-Amino-4-Sulfonatonaphthalen-2-Yl) Diazen-1-Yl] Phenyl} Phenyl) Diazen-1-Yl]Naphthalene-1-Sulfonate (Congo Red) at 303K

Table 6: Ultrasonic velocity and related acoustical parameters in the solution of nickel-Disodium-4-Amino-3-[(E)-2-(4-{4[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl) Phenyl}

Phenyl)

Diazen-1-Yl]

Diazen-1-Yl]


(Congo Red) at 303K

Table 4: Ultrasonic velocity and related acoustical parameters in the solution of lead-Disodium-4-Amino-3-[(E)-2-(4-{4-[(E)47 | IJBRITISH Vol.1 2014 Issue 1 May-June

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Figure-4: Metal complexes of Disodium 4-Amino-3-[(E)-2-(4{4-[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl)Diazen-1-Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene--Sulfonate (Congo Red) Solution (Ultrasonic Velocity Vs Solvents (DMSO and pH solutions)) in different Concentration at 303 K. (Table5.4.1-5.4.5) (where a=0.2 and b=0.4)

Table 7: Ultrasonic velocity and related acoustical parameters in the solution of copper-Disodium-4-Amino-3-[(E)-2-(4-{4[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl) Phenyl}

Phenyl)

Diazen-1-Yl]

Diazen-1-Yl]


(Congo Red) at 303K

(c)


Diazen-1-

Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) Solution (Ultrasonic Velocity Vs Solvents (DMSO and pH solutions)) in different Concentration at 303 K. (Table- 5.4.1-5.4.5) (where c=0.6)

(a)

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Diazen-1-

Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) (Adiabatic Compressibility Vs Solvents (DMSO and pH solutions)) in different Concentration at 303 K. (where a=0.2 and b=0.4)

Figure-8: Metal complexes of of Disodium 4-Amino-3-[(E)-2(4-{4-[(E)-2-(1-Amino-4-Sulfonatonaphthalen-2-Yl) Diazen-1Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) Solution (Intermolecular Free Length Vs Solvents (DMSO and pH solutions)) in different Concentration at 303 K. (Where a=0.2, b=0.4 and c=0.6)

2.6 CYCLIC VOLTAMETRIC STUDIES OF (c)

DYES WITH METAL


Diazen-1-

Yl] Phenyl} Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) (Adiabatic Compressibility Vs Solvents (DMSO and pH solutions)) in different Concentration at 303 K. (where c=0.6)

COMPLEXES Organic chemists have applied the technique to the study of biosynthesis reaction pathways and to study the electro chemically generated free radicals. An increasing number of inorganic chemists have been using CV to elevate the effects of ligand on the oxidation/reduction potential of the central metal ion in complexes and multinuclear clusters. This type of information plays an integral part in many of the approaches directed toward solar energy conversion and in metal studies of enzymatic catalysis. Knowledge of the electro chemistry of a metal complex can be useful in the selection of the proper oxidising agent to put the metal complex in an intermediate oxidation state. Electrochemical methodology has also been exploited as a novel means of introducing functional

(a)

group and removing blocking agents. Solid-state

analysis

relies

largely

on

various

spectroscopic and diffraction methods there are no functional reasons for the lack of electro chemical methods for solid-state analysis. However, there are practical reasons for this situation most importantly, until recently, there were no handy methods available for the study of the electro chemistry of any solid sample independent of its electrical conductivity, solubility etc.

(b) 49 | IJBRITISH Vol.1 2014 Issue 1 May-June

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Since

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electro

chemistry

always

mirrors

the

thermodynamic and kinetics of interfacial reactions it follows


Diazen-1-Yl]

Phenyl}

Phenyl)

Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red).

thus electro chemical measurements on solid compounds may provide valuable information concerning and quantitative composition, chemical equlibria and kinetics of a solid compound. Of course, it is clear that we cannot get direct information concerning crystal structure, bond length, bond angles etc. CV consists of cycling the potential of an electrode, which is immersed in an unstirred solution and measuring the resulting current. The potential of this working electrode is controlled versus a reference electrode (SCE or a silver/ silver

(c)

chloride electrode (Ag/AgCl)). The controlling potential, which is applied across these two electrodes, can be considered as excitation signal. The cyclic voltagramm of all metallo complexes are shown in the figure.9 and 10. The reduction process of the metallo dyes are quasi reversible in nature evidenced from the following criteria

(d) Figure -10: Cyclic voltagram of (c) nickel and (d) copper complexes of of Disodium 4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1Amino-4-Sulfonatonaphthalen-2-Yl)

Diazen-1-Yl]

Phenyl}

Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo red).

(a)

The cyclic voltammogram of the nickel and cobalt complexes of Disodium 4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1Amino-4-Sulfonatonaphthalen-2-Yl)

Diazen-1-Yl]

Phenyl}

Phenyl) Diazen-1-Yl] Naphthalene-1-Sulfonate (Congo Red) shows fig 5.4.3 (c and d) that the oxidation (anodic) and reduction of Ni (II) in the complex is characterized by a welldefined redox peaks at -825 V (anodic) and -750 V (cathodic) vs. SCE that remained stable after the cycle. This reversible process

is

usually

assumed

to

be

a

single-electron

reduction/oxidation of the couple Ni2+/Ni3+//Ni3+/Ni2+in the metallic centre of the complexes, and that the oxidation (anodic) and reduction of Cu (II) in the complex is

(b)

characterized by a well defined redox peaks at -825 V (anodic)

Figure-9: Cyclic voltagram of (a) lead and (b) Zinc complexes

and -725 V (cathodic) vs. SCE that remained stable after the

of of Disodium 4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1-Amino-4-

cycle. This reversible process is usually assumed to be a single50 | IJBRITISH

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electron reduction/oxidation of the couple Cu3+/ Cu2+ // 2+

3+

4.

S.B. Monaco, L.E. Davis, S.P. Velsko, F.T. Wong and D.

Cu /Cu in the metallic centre of the complexes (22-26).

Eimerl, J. Cryst. Growth, 85,

CONCLUSIONS

252(1987).

In the present investigation, the crystal growth of

5.

P. Gunter, Ch. Bosshard, K. Sutter, H. Arend, G.Chapuis,

marine Disodium 4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1-Amino-4-

R.J. Twieg and D. Dobrowolski,Appl. Phys. Lett., 50, 486


(1997).

Diazen-1-Yl]

Phenyl}

Phenyl)

Diazen-1-Yl] Naphthalene-1-Sulfonate dye (Congo red) was

6.

successfully carried out under standard laboratory conditions.

Lett., 62, 4414 (2008).

Since the crystallization of these dyes could culminate in good

7.

complex formation with transition metals, this part of the work

Lett., 64, 2477(1994).

was attempted and successfully implemented. The marine dye

8.

was made to form complex with the transition elements such as

F.E.A. Melo, J.Mendes Filho and

Ni, Cu, Pb and Zn in order to study about their complexing

S.C.Zilio, Opt. Mater., 6, 147 (1996).

ability degradation behaviour.

9.

The dye with metals shows the formation of a

C. Krishnan, P. Selvarajan and T.H. Freeda, Mater.

M. Kitazawa, R. Higuchi and M. Takahashi, Appl. Phys.

L. Misoguti, A.T. Varela, F. D. Nunes, V.S. Bagnato,

S.K. Kurtz and T.T. Perry, J. Appl. Phys., 39, 3798

(1968).

coordination complex with a tetrahedral geometry. The FTIR

10. X.Q. Wang, D. Xu, M. Lu, D. Yuan, J. Huang, X.Cheng, T.

spectrum shows the successful incorporation of Ni metal inside

Xie, G.H. Zhang, S.L.Wang,

the tetrahedral sites. The UV-Vis spectrum obtained for this

Wang, J. Crystal Growth 234 (2002) 469.

complex demonstrates its strong degradation behaviour besides

11. X.L. Duan, D.R. Yuan, X.Q.Wang, S.Y. Guo, J.G.Zhang,

proves the formation of stoichiometric complex. The redox

D. Xu, M.K. Lu, Cryst.

behaviour of the complex was amply substantiated by the

S.Y.Guo, J.R. Liu, Z.H. Yang, P.

Res.Technol. 37 (2002) 1066.

cyclic voltammetric studies. The degradation behaviour of the

12. C.C. Frazier, M.P. Cockerhamn, E.A. Chauchard,C.H.

samples was also substantiated by performing ultrasonic

Lee, J. Opt. Soc. Am. B 4

studies which shows that all the samples possess magnificent

(1987) 1899.

degradation behaviour.

13. S.B. Monaco, L.E. Davis, S.P. Velsko, F.T. Wong,D.

ACKNOWLEDGMENT

Eimerl, J. Crystal Growth 85(1987) 252.

The authors are thankful to Head of the department of chemistry,

Mahendra

Engineering

College

and

AMET

University to do the present work and also very thankful to Cochin University, Kerala for providing to utilize research lab for all the analysis. REFERANCES 1.

1X.Q. Wang, D. Xu, M. Lu, D. Yuan, J. Huang, X.Cheng,

T. Xie, G.H. Zhang, S.L. Wang, S.Y. Guo, J.R. Liu, Z.H. Yang and P. Wang, J. Cryst.Growth, 234, 469 (2002). 2.

X.L. Duan, D.R. Yuan, X.Q. Wang, S.Y. Guo, J.G. Zhang,

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14. P. Gunter, Ch. Bosshard, K. Sutter, H. Arend, G.Chapuis, R.J. Twieg, D. Dobrowolski, Appl. Phys.Lett. 50 (1997) 486.78 15. C. Krishnan, P. Selvarajan, T. H. Freeda, Material Letters, 62 (2008) 4414. 16. Jayandran M., and Balasubramanian V., “Growth and characterization of new organic marine dye NLO material: 6amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,

2,4,7,8,8a,8b-

octahydroazireno[2',3':3,4] pyrrolo [1,2-a] Indol- 8-yl] methyl carbamate”, E-Journal of chemistry., 8(4) (2011) 1797- 1067. 17. Jayandran M., and Balasubramanian V., “Growth and characterization of a neworganic marine dye NLO material: 7bromo-6-chloro-3-[3-[(2r, oxopropyl]-

3s)-3-hydroxy-2-piperidyl]-2

4(3h)-Quinazolinone”,

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18. Jayandran M.,and. Balasubramanian V., Crystal growth and spectroscopic stdies of marine dye NLO material: 4amino-3,6-bis[[4-[[4-chloro-6-[(3-sulfophenyl)amino]-1,3,5triazin-2-yl]amino]-2-sulfophenyl]azo]-5-hydroxy-2,7naphthalenedisulfonic acid hexasodium salt (reactive green 19) crystals, Asian Journal of Chemistry.,24(5)(2012) 29312935. 19. Jayandran M.and Balasubramanian V., “Synthesis, Growth and Spectroscopic Studies of Marine Dye NLO Material:

Disodium

2-(1,3-Dioxoinden-2-Yl)Quinoline-6,8-

Disulfonate (Quinoline Yellow) Crystals” , International Journal of Applied Chemistry., 4(1) (2012) 1-8. 20. Jayandran M., and Balasubramanian V., “Synthesis, Growth And Spectroscopic Studies Of Marine Dye NLO Material: Disodium 4-Amino-3-[(E)-2-(4-{4-[(E)-2-(1-Amino4-Sulfonatonaphthalen-2-Yl) Diazen-1-Yl] Phenyl} Phenyl) Diazen-1-Yl Naphthalene-1- Sulfonate”, International Journal of Applied Chemistry., 4(2) (2012)103-110. 21. Jayandran .M, Anand. B and Balasubramanian. V “Electrochemical Studies Of Marine Dyes With Some Cu (Ii), Ni (Ii), Zn(Ii) And Pb (Ii) Metal Complexes Of 4-Amino-3, 6Bis [[4-[[4-Chloro-6-[(3-Sulfophenyl) Amino]-1,3,5-Triazin-2Yl]Amino]-2-Sulfophenyl]Azo]-5-Hydroxy-2,7Naphthalenedisulfonic Acid Hexasodium Compound ”,Elixir Ultrasonics., 46(2012)8268-8272 22. B. Suresh Kumar, M.R. Sudarsana Kumar and K. Rajendra Babu, Cryst. Res. Technol., 43,745 (2008). 23. C. Razzetti, M. Ardoino, L. Zanotti, M. Zha and C. Paorici, Cryst. Res.Technol., 37, 456 (2002). 24. K. Yamada, A. Sato, T. Shimizu, T. Yamazaki and S. Yokoyama, Acta Cryst. E, 64, 806 (2008). 25. P. Selvarajan, J. Glorium Arul Raj and S. Perumal, J. Crystal Growth, 311, 3835 (2009). 26. G. Socrates, Infrared and Raman Characteristic Group Frequencies,Wiley, New York, edn. 3(2001).
