Synthesis, spectral characterization of azo dyes derived from calix[4]resorcinarene and their application in dyeing of fibers

Abstract

Seven new upper rim functionalized azocalix[4]resorcinarene dyes have been synthesized by coupling calix[4]resorcinarene with different diazo compounds of p-chloroaniline, p-nitroaniline, p-toludine, p-anisidine, p-aminobenzoic acid, o-aminophenol, and aniline. The characterization of these dyes has been carried out by elemental analysis, FT-IR, 1 H-and 13 C-NMR. Effect of solvents of varying dielectric constants on the absorption spectra of substituted and unsubstituted azocalix[4]resorcinarene dyes have been examined by UV-vis spectrophotometer. These azocalix[4]resorcinarene dyes have also been used for dyeing textile fibers like cotton, silk, and wool. Their dyeing and fastness properties have also been discussed.

Synthesis, Characterization, Solvatochromic Properties, and Antimicrobial‐radical Scavenging Activities of New Diazo Dyes Derived from Pyrazolo[1,5‐a]pyrimidine

“…In addition, the relationship between solvent polarity and dielectric constant is proportional. . For the UV measurements, we used the following solvent dielectric constants (ε): DMSO (46.45), DMF (36.71), acetonitrile (35.94), methanol (32.66), acetic acid (6.17), and chloroform (4.89) .…”

Surface Modification of Poly(GMA-co-EDMA-co-MMA) with Resorcarenes

“…Resorcarenes represent a class of macrocyclic phenolic compounds obtained from the condensation reaction of resorcinol with several aldehydes in acidic solutions, 3 and they can be modified with various substituents on the upper and lower rim to provide specific functionality and selectivity. The many possible structural variations lead to potential applications as voltammetric sensors, 4 dendrimer synthesis, 5,6 dyeing of fibers, 7,8 nuclear magnetic resonance (NMR) solvating agents, 9,10 chemical receptors for molecules and ions [11][12][13] and absorption of heavy metal ions, 14,15 besides, resorcarene derivatives can be absorbed or covalently bound to multiple surface types. Thus resorcarenes are used in high performance liquid chromatography (HPLC) for modification of the stationary phase, and the process involves the lower rim of the resorcarene derivate with polar carbonate groups covalently bonded to a silica substrate.…”

“…Tetrasodium 2,8,14,3.1.13,7 .1 9,13 .115,19 ]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,10,16,22-tetraol-6,12,18,24-tetrakis(olate) (5) was obtained as a creamcolored powder at a yield of 45%; mp > 250 °C decomposition; FTIR (KBr) n / cm -1 3319 (O-H), 1210 (C-O), 1609 (aromatic ring), 2929 (alkyl chains); 1 H NMR (400 MHz, DMSO-d 6 ) d 0.91 (t, 12H, CH 3 ), 1.22 (m, 8H, CH 2 ), 2.15 (q, 8H, CH 2 ), 4.18 (t, 4H, CH), 6.05 (s, 4H, ortho to OH), 7.25 (s, 4H, meta to OH), 9.56 (s, 4H, OH); 13 C NMR (100 MHz, DMSO-d 6 ) d 13.9 (CH 3 ), 20.8 (CH 2 ), 32.6 (CH 2 ), 34.9 (CH), 102.8, 124.0, 132.4, 152.3 (resorcinol ring).…”

Synthesis and <i>In Vitro</i> Evaluation of C-methylcalix[4]resorcinaryl octacinnamate and C-methylcalix[4]resorcinaryl octabenzoate as the Sunscreen

“…Calix [4]resorcinarenes are analogs of calixarene having two hydroxyl groups on benzene rings at an extra annular position forming a macrocycle. The compounds are synthesized by the acid-catalyzed cyclocondensation of resorcinol with various aliphatic or aromatic aldehyde [8][9][10]. The compounds are easily synthesized by well-established one-pot procedures [9].…”

“…The compounds are easily synthesized by well-established one-pot procedures [9]. They have found much application of Calix [4]resorcinarenes such as macrocyclic receptor [11], host molecules [12][13][14], dying fiber [10], building blocks for even larger supramolecular architectures assemblies such as cages, capsule and as starting materials for the preparation of more sophisticated molecules [15]. Unfortunately, the study of calix [4]resorcinarene as the ultraviolet light absorbers has attracted very little attention.…”