Synthesis of Silver– 4,4’-diaminodiphenyl –Cyclodextrin Nanomaterials and pH Dependent Characteristics of 4,4’-diaminodiphenyl –Cyclodextrin Inclusion Complexes

Authors

N. Rajendiran

Department of Chemistry, Annamalai University, Annamalai Nagar, Tamilnadu (India)

P. Ramasamy

Molecular Biophysics Unit, Indian Institute of Science, Bangalore (India)

P. Senthilraja

Department of Bioinformatics, Bharathidasan University, Trichy - 620024 (India)

S. Senthilmurugan

Department of Zoology, Annamalai University, Annamalai Nagar, Tamilnadu (India)

Article Information

DOI: 10.51244/IJRSI.2026.1303000024

Subject Category: Chemistry

Volume/Issue: 13/3 | Page No: 249-257

Publication Timeline

Submitted: 2026-03-07

Accepted: 2026-03-13

Published: 2026-03-25

Abstract

The spectral characteristics of 4,4’-diaminodiphenyl (benzidine, DADP) in various solvents, and in the presence of α-cyclodextrin (α-CD) and β-cyclodextrin (β-CD) at pH~3 and pH~7, were investigated using UV–visible, fluorescence, time-resolved fluorescence measurements, and PM3 computational methods. Ag:DADP:CD nanomaterials were synthesized and characterized by SEM, DSC, FTIR, 1H NMR and XRD techniques. Both pH conditions, DADP exhibited distinct absorption and emission shifts upon complexation with α-CD and β-CD. DADP showed a single broad emission band in all solvents, and CD solutions indicates the presence of twisted intramolecular charge transfer (TICT) in the DADP molecule. The fluorescence lifetimes of the inclusion complexes were greater than that of free DADP. In the DADP molecule, both the vertical and horizontal bond lengths between the amino and hydroxy groups are smaller than the β-CD cavity size. SEM–EDX data confirmed the presence of 5.5% silver in the nanomaterials.

Keywords

4,4’-diaminodiphenyl, cyclodextrin, silver nano

Downloads

References

1. M.Shanmugam, J.Thulasidhasan, G.Venkatesh, V. Chidambaranathan, N. Rajendiran, Effect of α- and β-cyclodextrins on three S-triazine derivates: Spectral and molecular modeling studies. Physics and Chemistry of Liquids, 52(2014) 583-600. doi.org/10.1080/00319104.2014.880437 [Google Scholar] [Crossref]

2. Spectrochimica Acta A, 74 (2009) 469–477, A.A. Smith, K.Kannan, R.Manavalan, N. Rajendiran* Spectral characteristics of tramadol drug in different solvents and β-CD. [Google Scholar] [Crossref]

3. M.Jude Jenita, G.Venkatesh, J.Thulasidasan, N. Rajendiran, Excimer formation in inclusion complexes of antihypertensive drugs with HP-α- and HP-β-CDs. Indian J. Chemistry, 52A (2013) 207-216. [Google Scholar] [Crossref]

4. N. Rajendiran, R.K. Sankaranarayanan, Nanorod formation of cyclodextrin covered sudan dyes through supramolecular self assembly. J. Experimental Nanoscience, 10 (2015) 407-428, doi. 10.1080/17458080.2013.840934 [Google Scholar] [Crossref]

5. Polycyclic Aromatic Compounds, 42 (2022) 3563-3585, N. Rajendiran, A. Antony Muthu Prabhu, T. Mohandoss, J. Thulasidhasan, R. Baskaran, Spectral and theoretical investigation of inclusion complex between cinnamic acid and hydroxycinnamic acids with native cyclodextrins. DOI: 10.1080/10406638.2020.1869794. [Google Scholar] [Crossref]

6. RK. Sankaranarayanan, G.Venkatesh, Jayashree Ethiraj, M.Pattabiraman, K.Saravanakumar G.Arivazhagan, R.Shanmugam, N.Rajendiran, Stepwise pesudopolyrotaxane nanostructure formation from supramolecular self-assembly by inclusion complexation of fast violet B with α- and β-cyclodextrins. J.Molecular Structure 1262(2022)133080-89, doi. 10.1016/j.molstruc.2022.133080 [Google Scholar] [Crossref]

7. Indian J. Chemistry, 52A (2013) 207-216, M.Jude Jenita, G.Venkatesh, V.K.Subramanian, N. Rajendiran*, Excimer formation in inclusion complexes of antihypertensive drugs with HP-α- and HP-β-CDs. [Google Scholar] [Crossref]

8. N. Rajendiran, T. Mohandoss, J. Thulasidhasan, Dual Fluorescence of 4,4′-sulfonyldiphenol, 3,3’–dimethyl 4,4′-sulfonyldiphenol, 4,4′-sulfonyldibenzoic acid: Effects of cyclodextrin complexation. Canadian Chemical Transactions, 3(2015) 319-332. Doi. 10.13179/canchemtrans.2015.03.03.0225 [Google Scholar] [Crossref]

9. N. Rajendiran, A. Antony Muthu Prabhu, T. Mohandoss, J. Thulasidhasan, R. Baskaran, Spectral and theoretical investigation of inclusion complex between cinnamic acid and hydroxy cinnamic acids with native cyclodextrins. Polycyclic Aromatic Compounds, 42 (2022) 3563-3585, [Google Scholar] [Crossref]

10. N. Rajendiran, J. Thulasidhasan, M. Jude Jenita, Guest - Host inclusion complex formation of 2-, 3-, and 4-aminobenzoic acids with native and modified cyclodextrins. International Letters of Chemistry, Physics and Astronomy, 69(2016)10-21, doi.org/10.56431/p-ira6yv [Google Scholar] [Crossref]

11. A. Mani, P. Ramasamy, A. Antony Muthu Prabhu, N. Rajendiran, Investigation of Ag and Ag/Co bimetallic nanoparticles with naproxen-cyclodextrin inclusion complex. J. Molecular Structure, 1284 (2023) 135301-10. doi.org/10.1016/j.molstruc.2023.135301 [Google Scholar] [Crossref]

12. A. Mani, P. Ramasamy, A. Antony Muthu Prabhu, P. Senthilraja, N. Rajendiran, Synthesis and Analysis of Ag/Olanzapine/Cyclodextrin and Ag/Co/Olanzapine/Cyclodextrin Inclusion Complex Nanorods. Physics and Chemistry of Liquids, 62 (2024) 196-209. doi.org/10.1080/00319104.2023.2297223 [Google Scholar] [Crossref]

13. A. Mani, G. Venkatesh, P. Senthilraja, N. Rajendiran, Synthesis and Characterisation of Ag-Co-Venlafaxine-Cyclodextrin Nanorods, European J Advanced Chemistry Research, 5 (2024) 9-16. doi; 10.24018/ejchem.2024.5.1.147 [Google Scholar] [Crossref]

14. A.Mani, P.Ramasamy, A.Antony Muthu Prabhu, P.Senthilraja, N.Rajendiran, Synthesis and Characterisation of Ag/Co/Chloroquine/Cyclodextrin Inclusion Complex Nanomaterials. J Sol-Gel Science and Technology 115 (2025) 844-856. doi.org/10.1007/s10971-024-06620-5. [Google Scholar] [Crossref]

15. N. Rajendiran, A. Mani, M. Venkatesan, B. Sneha, E. Nivetha, P. Senthilraja, Spectral, Microscopic, Antibacterial and Anticancer Activity of Pyrimethamine drug with Ag nano, DNA, RNA, BSA, Dendrimer, and Cyclodextrins, J Solution Chem, In press. [Google Scholar] [Crossref]

16. P Ramasamy, A Mani, B Sneha, E Nivetha, M Venkatesan, N Rajendiran, Azo-hydrazo tautomerism in Sudan Red-B and Cyclodextrin/ Sudan Red-B doped ZnO nanomaterials. J Molecular Structure 1329 (2025) 141423-32. doi.org/10.1016/j.molstruc.2025.141423 [Google Scholar] [Crossref]

17. J.Prema Kumari, A. Antony Muthu Prabhu, G.Venkatesh, V.K.Subramanian, N. Rajendiran, Spectral characteristics of sulfadiazine, sulfisomidine: Effect of solvents, pH and β-CD. Physics and Chemistry of Liquids, 49(2011)108–132. doi.org/10.1080/00319104. 2010.509724 [Google Scholar] [Crossref]

18. R.K.Sankaranarayanan, S.Siva, A. Antony Muthu Prabhu, N.Rajendiran, A study on the inclusion complexation of 3,4,5-trihydroxybenzoic acid with β-CD at different pH. J.Inclusion Phenomena and Macrocyclic Chemistry, 67 (2010) 461-470. doi.org/10.1007/s10847-009-9729-0 [Google Scholar] [Crossref]

19. N. Rajendiran, S. Siva, J. Saravanan, Inclusion complexation of sulfa pyridine with α- and β-CDs: Spectral and molecular modeling study. J. Molecular Structure,1054-1055 (2013) 215–222. doi.org/10.1016/j.molstruc.2013.09.035 [Google Scholar] [Crossref]

20. N. Rajendiran, R.K. Sankaranarayanan, Azo dye/Cyclodextrin: New findings of identical nanorods through 2:2 inclusion complexes. Carbohydrate Polymers, 106 (2014) 422-431. doi.org/10.1016/j.carbpol.2014.01.030 [Google Scholar] [Crossref]

21. N. Rajendiran, R.K. Sankaranarayanan, J.Saravanan, A study of supramolecular host–guest interaction of dothiepin and doxepin drugs with cyclodextrin macrocycles. J Molecular Structure, 1067(2014) 252-260. doi.org/10.1016/j.molstruc.2014.03.051 [Google Scholar] [Crossref]

22. A. Antony Muthu Prabhu, N.Rajendiran, Encapsulation of labetalol, and pseudoephedrine in β-CD cavity: Spectral and molecular modeling studies. J. Fluorescence, 22(2012)1461-1474. doi.org/10.1007/s10895-012-1083-8 [Google Scholar] [Crossref]

23. M.Jude Jenita, A.Antony Muthu Prabhu, N.Rajendiran, Theoretical study of inclusion complexation of tricyclic antidepressant drugs with β-CD. Indian J. Chemistry A, 51A (2012) 1686-1694. [Google Scholar] [Crossref]

24. N. Rajendiran, G. Venkatesh, J.Saravanan, Supramolecular aggregates formed by sulfadiazine and sulfisomidine inclusion complexes with α- and β-cyclodextrin. Spectrochimica Acta, 129A (2014) 157-162, https://doi.org/10.1016/j.saa.2014.03.028 [Google Scholar] [Crossref]

25. N. Rajendiran, G. Venkatesh, T.Mohandoss, Fabrication of 2D nano sheet through self assembly behavior of sulfamethoxy pyridazine inclusion complex with α- and β-cyclodextrins. Spectrochim Acta A,123A (2014) 158-166, doi.org/10.1016/j.saa.2013.12.053 [Google Scholar] [Crossref]

26. S.Siva, R.K.Sankaranarayanan, A.Antony Muthu Prabhu, N.Rajendiran, Inclusion complexation of 3,5-dihydroxy benzoic acid with β-CD at different pH. Indian J. Chemistry, 48A (2009)1515–1521, [Google Scholar] [Crossref]

27. A.Antony Muthu Prabhu, G.Venkatesh, N.Rajendiran, Azo-Hydrazo tautomerism in 1-phenyazo-2-naphthol dyes in various solvents, pH and β-CD. J. Fluorescence, 20 (2010) 961–972. Doi. 10.1007/s10895-010-0642-0 [Google Scholar] [Crossref]

28. N. Rajendiran, R. K. Sankaranarayanan, G. Venkatesh, Excimer emission in inclusion complexes of dibenzofuran and 5-dibenzosuberenone with α- and β-cyclodextrins. Bull Chem Soc Japan, 87(2014) 797-808, doi.org/10.1246/bcsj.20140057 [Google Scholar] [Crossref]

29. A.A.Smith, K.Kannan, R.Manavalan, N.Rajendiran, Intramolecular charge transfer effects on flutamide drug. J. Fluorescence, 20(2010)809–820, doi. 10.1007/s10895-010-0623-3 [Google Scholar] [Crossref]

30. A.Antony Muthu Prabhu, G.Venkatesh, N.Rajendiran, Unusual spectral shifts of imipramine and carbamazepine drugs. J. Fluorescence, 20 (2010) 1199–1210, doi. 10.1007/s10895-010-0669-2 [Google Scholar] [Crossref]

Metrics

Views & Downloads

Similar Articles