Auramine-O dye abnormal Stokes shift in aqueous solution due to J-aggregate formation

Hassanzadeh, Ali

doi:10.66224/CNJ.3.4.791

Auramine-O dye abnormal Stokes shift in aqueous solution due to J-aggregate formation

Document Type : Original Article

Author

Ali Hassanzadeh

Physical Chemistry, Chemistry, Urmia University, Urmia, Iran

10.66224/CNJ.3.4.791

Abstract

Auramine-O (Au-O) dye is an imine type colorant which is used in many industrials such as food, textile, leader, printing, optic, biomedical, laser and so on. In spite of its spread applications, Au-O dye is toxic and resistant in the environment, aquatic organisms and human body. Hence, it’s using is banned in many countries. Consequently, identification and determination of Au-O is a necessary routine work in Analytical chemistry. On the other hand, there are many unanswered questions about Au-O dye’s behavior in aqueous solution at different acidity and concentration for using it in other applications which we attempted to address here. Hence, in this work, Au-O dye’s absorbance, fluorescence and aggregation behaviors were revisited. We showed that Au-O dye forms J-aggregate macromolecule in very acidic aqueous solution (pH=0.5) and high concentration (10-2 M) as red color solution with a λmax=295 nm and a shoulder peak located at 537 nm in UV-vis. spectrum. This molecular J-aggregate showed fluorescence emission at λmax=537 nm which has not been reported, so far. A Stokes shift of 120 nm for J-aggregate indicates that this dye is likely to be a suitable candidate for fluorescent microcopy and does not suffer from low signal-to-noise ratio and self-quenching problems. We also showed that using the Stephen’s reduction reaction, Au-O can be converted directly to corresponding colorless Michler’s ketone without oxidative complextation. Finally, we reveal that fluorescence of Au-O has been unchanged by a magnetic field.

Graphical Abstract

Keywords

Auramine-O

Stokes shift

Excited state proton transfer

Stephen&rsquo

s reduction reaction

Michler&rsquo

s ketone

1. Xiaogang Liu, Jacqueline M. Cole, Philip C. Y. Chow, Lei Zhang, Yizhou Tan, and Teng Zhao, Dye aggregation and complex formation effects in 7‑(diethylamino)-coumarin-3-carboxylic Acid, J. Phys. Chem. C, dx.doi.org/10.1021/jp409435v.

2. Xiran Yang, Simin Liu, J-type dimer of Auramine-O dye upon encapsulation in cucurbit[8]uril host showing intense excimer emission, Dyes and Pigments, 159 (2018) 331-336.

3. Ylning ZHANG, REZIK A. AGBARIA, and ISIAH M. WARNER, Complexation studies of water-soluble calixarenes and Auramine-O dye, Supramolecular Chemistry, 1997, Vol. 8, pp. 309-318.

4. Nadav Amdursky and Dan Huppert, Auramine‑O as a Fluorescence Marker for the Detection of Amyloid Fibrils, J. Phys. Chem. B 116 (2012) 13389−13395. dx.doi.org/10.1021/jp310232b.

5. R Simkovitch, K Akulov, Y Erez, N Amdursky, R Gepshtein, T Schwartz and D Huppert, Acid effect on excited Auramine-O molecular rotor relaxations in solution and adsorbed on insulin fibrils, Methods Appl. Fluoresc. 3 (2015) 034005.

6. Cristina Pei Ying Kong, Nurul Amanina A. Suhaimi, Nurulizzatul Ningsheh M. Shahri, Jun-Wei Lim, Muhammad Nur, Jonathan Hobley and Anwar Usman, Auramine-O UV Photocatalytic Degradation on TiO₂ Nanoparticles in a Heterogeneous Aqueous Solution, Catalysts 2022, 12, 975. https://doi.org/10.3390/catal12090975.

7. Silvano R. Valandro, Alessandra L. Poli, Miguel G. Neumann, Carla C. Schmitt, Photophysics of Auramine-O adsorbed on solid clays, Journal of Luminescence, 161 (2015) 209-2016.

8. Tian-Bing Ren, Wang Xu, Wei Zhang, Xing-Xing Zhang, Zhi-Yao Wang, Zhen Xiang, Lin Yuan, and Xiao-Bing Zhang, A General Method to Increase Stokes Shift by Introducing Alternating Vibronic Structures, J. Am. Chem. Soc. 140 (2018) 7716−7722.

9. Okonkwo, R. C, Anyabolu, A. E, Onwunzo M. C, Ifeanyichukwu, M. O, Chukwuka, C. P, Enemuo, E, Ngwu A. M, A Comparative Study of Auramine O Staining Using LED Fluorescent Microscopy with Ziehl –Neelsen Staining in the Examination of Sputum For Acid Fast Bacilli, JMSCR,03, (08) (2015) 6987-6991.

10. R Simkovitch, K Akulov, Y Erez, N Amdursky, R Gepshtein, T Schwartz and D Huppert, Acid effect on excited Auramine-O molecular rotor relaxations in solution and adsorbed on insulin fibrils, Methods Appl. Fluoresc. 3 (2015) 034005.

11. Jingjing YAN, Xin HUANG, Shaopu LIU, Jidong YANG, Yusheng YUAN, Ruilin DUAN, Hui ZHANG, and Xiaoli HU, A Simple and Sensitive Method for Auramine-O detection based on the binding Interaction with bovine serum albumin, ANALYTICAL SCIENCES, 32 (2016) 819-824.

12. Thuong Nguyen Thi Kim , Thi Thu Bui, Anh Tuan Pham, Van Thang Duong, and Thi Huong Giang Le, Fast determination of Auramine-O in food by adsorptive stripping voltammetry, journal of analytical methods in chemistry, 2019, Article ID 8639528, 6 pages, https://doi.org/10.1155/2019/8639528.

13. Rahmat Ali, Tahira Mahmood*, Abdul Naeem, Abid Ullah, Madeeha Aslam, Sheraz Khan, Process optimization of Auramine-O adsorption by surfactant-modified activated carbon using Box–Behnken design of response surface methodology, Desalination and Water Treatment, 217 (2021) 367–390, doi: 10.5004/dwt.2021.26740.

14. Nadav Amdursky and Dan Huppert, Auramine‑O as a Fluorescence Marker for the detection of amyloid fibrils, J. Phys. Chem. B 116, (2012) 13389−13395. dx.doi.org/10.1021/jp310232b.

15. Ankur A. Awasthi and Prabhat K. Singh, Stimulus-Responsive Supramolecular Aggregate Assembly of Auramine O Templated by Sulfated Cyclodextrin, J. Phys. Chem. B 2017, 121, 6208−6219. DOI: 10.1021/acs.jpcb.7b03592.

16. Ankur A. Awasthi, Shrishti P. Pandey, and Prabhat K. Singh, Supramolecular Control on the Optical Properties of a Dye-Polyelectrolyte Assembly, ChemPhysChem, 22, 2021, 1 – 11. doi.org/10.1002/cphc.202100092.

17. Gerald Oster and Yasunori Nishijima, Fluorescence and internal rotation: Their dependence on viscosity of the medium, Fluorescence and internalrotation,78 (1956) 1581-1584.

18. Felix Kaspar, Quality Data from Messy Spectra: How Isometric Points Increase Information Content in Highly Overlapping Spectra, ChemBioChem 2023, 24, e202200744 (1 of 7).

19. L. E. Vidal Salgado, C. Vargas-Hernández, Spectrophotometric Determination of the pKa, Isosbestic Point and Equation of Absorbance vs. pH for a Universal pH Indicator, American Journal of Analytical Chemistry, 2014, 5, 1290-130.

20. Kasha M., Rawls H. R. and Ashraf El-Bayoumi M., The exciton model in molecular spectroscopy, 1103x0371.pdf (iupac.org)

21. Chern Chuang, Doran I.G. Bennett, Justin R. Caram, Ala´n Aspuru-Guzik, Moungi G. Bawendi, and Jianshu Cao, Generalized Kasha’s Model: T-dependent spectroscopy reveals short-range structures of 2D excitonic systems, Chem., 5 (2019) 3135–3150.

22. Yang-Hui Luo, Cheng Xue, Shu-Xin Zhang, Jie Zhao, Xue-Ting Jina and Min Liu, Charge transfer-triggered reversible spin-state switching, J. Mater. Chem. C, 2024, 12, 1693-1700.

23. Yang-Hui Luo, Xue-Ting Jin, Shu-Xin Zhang, Cheng Xue and Min Liu, Dynamic Aggregation Triggering Reversible Spin-State Switching, ACS Appl. Mater. Interfaces 2023, 15, 48365-48374.

24. Siwei Sun, Min Liu, Xue-Ting Jin, Jie Zhao, Yang-Hui Luo, Wavelength-Based luminescence sensing via Turn-On responses for acid detection in complex Environments, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 326 (2025) 125187.

25. Cushing, S.K., et al., Origin of Strong Excitation Wavelength Dependent Fluorescence of Graphene Oxide. ACS Nano, 2014. 8(1): p. 1002-1013.

26. Ryota Matsuoka, Shojiro Kimura, Tomoaki Miura, Tadaaki Ikoma, Tetsuro Kusamoto, Single-molecule Magnetoluminescence from a Spatially Confined Persistent Diradical Emitter, JACS 145, 25 (2023) 13615-13620. DOI: 10.1021/jacs.ac01076.

27. Anthony P. Davis, 1.12 - Reduction of carboxylic acids to aldehydes by other methods, comprehensive organic synthesis, 8, (1991) 283-305.