Synthesis, spectral behavior and biological activity of some novel 1,3,4-oxadiazine cyanine dyes

Abstract

New methine cyanine dyes covering monomethine cyanine dyes and dimethine cyanine dyes derived from benzo [(2,3-b)benzoxazine; (2,3-e)1,3,4-oxadiazine]-5,12-dione were prepared. The electronic visible absorption spectra of all the synthesized cyanine dyes were investigated in 95% ethanol solution. Biological activity for a number of selected compounds was tested and evaluated against various bacterial strains (Bacillus subtilis, Escherichia coli, Pseudomona aeruginosa and Staphylococcus aureus). Structural determination was carried out via elemental analysis, visible, mass, IR and 1 H NMR spectroscopic data.

Theoretical Models, Preparation, Characterization and Applications of Cyanine J‐Aggregates: A Minireview

“…To determine the crystalline structure of the CJA, 1D and 2D NMR spectroscopy can be used. 1 H-and 13 C-NMR spectroscopy are commonly used for characterization of new cyanine syntheses. [62,70] The phase of the crystalline CJA can also be observed by NMR and XRD as well as the liquid crystal structure of the CJA.…”

“…[11] Depending on the substituent, the absorption of pentamethine derivatives can reach the NIR region (>750 nm), and heptamethine cyanines may show absorption even in the short‐wave infrared (SWIR) regime (>1000 nm), a unique property for these kind of molecules. [12] Longer cyanines can also be prepared, [13] but they are not commonly used because of their diminishing photostability, the broadening of their absorption spectrum [14] and the fact that their absorption decreases when extending the polymethine chain length. [15] However, the introduction of a cyclic rigid group in the polymethine chain can improve the stability of long‐chain cyanine dyes.…”

Novel Simple Cyanine, Carbocyanine, and Dicarbocyanine Dyes: Synthesis, Characterization and Application on Polyester Fabric

“…Substitution A = 1-ethyl pyridinium-4-yl salt in dye (4a) by A = 1-ethyl quinolinium-4-yl salt in dye (4b) caused a bathochromic shift of λmax = 75 nm, so compound (4b), exhibited λmax = 520 nm. This back to the more extensive π-delocalization and conjugation within the extra phenyl ring in quinolinium ring in dye (4b) (Table 2) (Ahmed et al, 2018;Gomaa et al, 2012;Shindy et al, 2019;Shindy et al, 2017;Shindy et al, 2015;Soriano et al, 2015;Shindy et al, 2018).…”

Antimicrobial and Dyeing Studies of Some Novel Reactive Mono(bis mono), Tri(bis tri) Methine Cyanine Dyes based on Cyano Pyridazine Nucleus

“…On the other side, trimethine (bis trimethine) cyanine dyes recorded absorption bands in regions (370-620 nm) and (370-630 nm) (Table 1). This indicates that the value of absorption bands, position and molar extinction coefficient was influenced by several factors, such as: the nature of heterocyclic quaternary residue (A), electron withdrawing or donating groups present in the molecule, the number of methine units and the number of charge transfer pathwayy (Powar et al, 2009;Gomaa, 2014;Henary et al, 2013;Gomaa et al, 2012;Ahmed et al, 2018;Shindy et al, 2019;Shindy et al, 2017;Soriano et al, 2016;Gomaa, 2019). So, the absorption spectra of dyes (4b, d), (5b, d), (8b, d) and (9b, d) is a red-shifted to dyes (4a, c), (5a, c), (8a, c) and (9a, c) respectively.…”