Physical, Thermal and Biological Properties of Yellow Dyes with Two Azodiphenylether Groups of Anthracene

Abstract

Two yellow bis-azo dyes containing anthracene and two azodiphenylether groups (BPA and BTA) were prepared, and an extensive investigation of their physical, thermal and biological properties was carried out. The chemical structure was confirmed by the FTIR spectra, while from the UV–Vis spectra, the quantum efficiency of the laser fluorescence at the 476.5 nm was determined to be 0.33 (BPA) and 0.50 (BTA). The possible transitions between the energy levels of the electrons of the chemical elements were established, identifying the energies and the electronic configurations of the levels of transition. Both crystals are anisotropic, the optical phenomenon of double refraction of polarized light (birefringence) taking place. Images of maximum illumination and extinction were recorded when the crystals of the bis-azo compounds rotated by 90° each, which confirms their birefringence. A morphologic study of the thin films deposited onto glass surfaces was performed, proving the good adhesion of both dyes. By thermal analysis and calorimetry, the melting temperatures were determined (~224–225 °C for both of them), as well as their decomposition pathways and thermal effects (enthalpy variations during undergoing processes); thus, good thermal stability was exhibited. The interaction of the two compounds with collagen in the suede was studied, as well as their antioxidant activity, advocating for good chemical stability and potential to be safely used as coloring agents in the food industry.

Unveiling All‐Optical Switching Phenomenon in Anthracene Derivatives: A Comprehensive Study on Optical and Nonlinear Optical Multifunctionality

“…S. R. Maidur et al previously offered theoretical confirmation of the all-optical switching abilities for the investigated anthracene derivatives (Br-ANC and Cl-ANC), based on CW z-scan measurements and the estimation of one-photon and two-photon merit factors for the growth crystals of these derivatives. [90] However, a focus solely on the optical anisotropy of other anthracene-based crystals (BPA and BTA) was confirmed recently through cross-polarized microscopy by C. A. Carabet et al [91] Moreover, a critical aspect of our study is the elucidation of the mechanisms governing these photoinduced molecular transitions within the considered materials, as supported by the theoretical analysis of light-driven phenomena presented earlier in this article (Chapter 3.1).…”

“…S. R. Maidur et al previously offered theoretical confirmation of the all‐optical switching abilities for the investigated anthracene derivatives (Br‐ANC and Cl‐ANC), based on CW z ‐scan measurements and the estimation of one‐photon and two‐photon merit factors for the growth crystals of these derivatives. [ 90 ] However, a focus solely on the optical anisotropy of other anthracene‐based crystals (BPA and BTA) was confirmed recently through cross‐polarized microscopy by C. A. Carabet et al [ 91 ]…”

“… b) ref [ 91 ] BPA: 9,10‐bis(((4′‐phenyldiazenyl)‐[1,1′‐biphenyl]−4‐yl)oxy)methyl)anthracene; BTA: 9,10‐bis(((4′‐p‐tolyldiazenyl)‐[1,1′‐biphenyl]−4‐yl)oxy)methyl)anthracene.…”

“…Summary of physical parameters pertaining to all-optical switching phenomena in the group of anthracene derivatives compounds.Compound film thickness (μm)Δn max ×10 −4 (-) Δn** ×10 −5 (-) n 2 ×10 −8 (m 2 W −1 ) n 2 ×10 −7 (cm 2 mW −1 ) 𝜒 (3) ×10 −10 (m 2 V −2 ); ** defined for I pump = 50.0 mW/cm 2 ; a) ref[ 90] Br-ANC: (2E)−1-(anthracen-9-yl)−3-(4-bromophenyl)prop-2-en-1-one; Cl-ANC: (2E)−1-(anthracen-9-yl)−3-(4-chlorophenyl)prop-2-en-1-one; defined based on the CW z-scan experiment; b) ref[91] BPA: 9,10-bis(((4′-phenyldiazenyl)-[1,1′-biphenyl]−4-yl)oxy)methyl)anthracene; BTA: 9,10-bis(((4′-p-tolyldiazenyl)-[1,1′-biphenyl]−4-yl)oxy)methyl)anthracene.…”