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<p>A series of 4,4′-dihydroxy-3-substituted azobenzene disperse dyes (<b>2a–f</b>) were synthesized, fully characterized (FT-IR, <sup>1</sup>H/<sup>13</sup>C NMR, CHN elemental analysis) and evaluated by DFT (B3LYP/6-31G(d, p)) to link electronic structure with dyeing performance. TD-DFT reproduces experimental λ<sub>max</sub> with deviations ≤ 12&#xa0;nm, supporting the computational model. Compound <b>2e</b> (3-CHO) shows the highest electrophilicity (ω = 4.6441&#xa0;eV) and dipole moment (µ = 4.9366 D), while dye <b>2d</b> (3-COOH) delivered the highest color strength (K/S = 21.64 in 5% DMF–95% H<sub>2</sub>O), corresponding to a ≈ 46.3% increase relative to the aqueous + dispersant system (K/S = 14.79). Exhaustion (%E) and fastness data (wash, perspiration, scorch, light) indicate generally commercial-grade fixation for the series, with light fastness uniformly high (7–8). We show that modest DMF addition (5% v/v) improves color uptake for some substituents but can slightly reduce certain fastness metrics; therefore DMF is used here as a mechanistic probe (improves solubility/partitioning under controlled lab conditions) rather than a recommended scale-up solvent. The combined experimental, DFT analysis identifies structure property rules to guide design of disperse dyes with improved color strength and predictable application behaviour.</p>

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Synthesis, DFT Analysis, and Dyeing Performance of 4,4’-Dihyroxy-3-Substituted Azobenzene Disperse Dyes with Comparative Evaluation of Aqueous and DMF-Based Application Systems

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年4月20日

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  • Mohamed A. El-Rahman,
  • Mai S. Alsubaie,
  • Mohamed A. El-Atawy,
  • Hussam Y. Alharbi,
  • Majed S. Aljohani,
  • Saad Alrashdi,
  • Alaa Z. Omar,
  • Ezzat A. Hamed,
  • Reham O. El-Zawawy

摘要

A series of 4,4′-dihydroxy-3-substituted azobenzene disperse dyes (2a–f) were synthesized, fully characterized (FT-IR, 1H/13C NMR, CHN elemental analysis) and evaluated by DFT (B3LYP/6-31G(d, p)) to link electronic structure with dyeing performance. TD-DFT reproduces experimental λmax with deviations ≤ 12 nm, supporting the computational model. Compound 2e (3-CHO) shows the highest electrophilicity (ω = 4.6441 eV) and dipole moment (µ = 4.9366 D), while dye 2d (3-COOH) delivered the highest color strength (K/S = 21.64 in 5% DMF–95% H2O), corresponding to a ≈ 46.3% increase relative to the aqueous + dispersant system (K/S = 14.79). Exhaustion (%E) and fastness data (wash, perspiration, scorch, light) indicate generally commercial-grade fixation for the series, with light fastness uniformly high (7–8). We show that modest DMF addition (5% v/v) improves color uptake for some substituents but can slightly reduce certain fastness metrics; therefore DMF is used here as a mechanistic probe (improves solubility/partitioning under controlled lab conditions) rather than a recommended scale-up solvent. The combined experimental, DFT analysis identifies structure property rules to guide design of disperse dyes with improved color strength and predictable application behaviour.