ArticleJournal of fluorescence2026
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.
Article in Journal of fluorescence, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
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.
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