Physicochemical and Nonlinear Optical Properties of Novel Environmentally Benign Heterocyclic Azomethine Dyes: Experimental and Theoretical Studies

S M Afzal; M A N Razvi; Salman A Khan; Osman I Osman; Ahmed H Bakry; Abdullah M Asiri

doi:10.1371/journal.pone.0161613

Physicochemical and Nonlinear Optical Properties of Novel Environmentally Benign Heterocyclic Azomethine Dyes: Experimental and Theoretical Studies

PLoS One. 2016 Sep 15;11(9):e0161613. doi: 10.1371/journal.pone.0161613. eCollection 2016.

Authors

S M Afzal^{1

2}, M A N Razvi¹, Salman A Khan³, Osman I Osman^{3

4}, Ahmed H Bakry¹, Abdullah M Asiri^{3

5}

Affiliations

¹ Physics Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.
² Physics Department, Aligarh Muslim University, Aligarh, 202002, India.
³ Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.
⁴ Chemistry Department, Faculty of Science, University of Khartoum, P.O. Box 321, Khartoum, 11111, Sudan.
⁵ The Center of Excellence for Advanced Materials, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.

Abstract

Novel heterocyclic azomethine dyes were prepared by the reaction of anthracene-9-carbaldehyde with different heterocyclic amines under microwave irradiation. Structures of the azomethine dyes were confirmed by the elemental analysis, mass spectrometry and several spectroscopic techniques. We studied absorbance and fluorescence spectra of the azomethine dyes in various solvents. They are found to be good absorbers and emitters. We also report photophysical properties like, extinction coefficient, oscillator strength, stokes shift and transition dipole moment. This reflects physicochemical behaviors of synthesized dyes. In addition, their intramolecular charge transfer and nonlinear optical properties, supported by natural bond orbital technique, were also studied computationally by density functional theory. The negative nonlinear refractive index and nonlinear absorption coefficient were measured for these dyes using the closed and open aperture Z-scan technique with a continuous wave helium-neon laser. These are found to vary linearly with solution concentration.

MeSH terms

Azo Compounds / chemistry*
Coloring Agents / chemistry*
Models, Theoretical
Optics and Photonics
Spectrometry, Fluorescence
Thiosemicarbazones / chemistry*

Substances

Azo Compounds
Coloring Agents
Thiosemicarbazones
azomethine

Grants and funding

This work was supported by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant no. (130-857-D1435). The authors, therefore, acknowledge the DSR technical and financial support (SMA).