Molecular insights into diazonium salt binding and colour development in wood substrates

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-09-01 DOI:10.1016/j.dyepig.2025.113202

Susanna Ortlieb, Avinash P. Manian, Thomas Bechtold, Tung Pham

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Abstract

Sustainable wood marking and tracking are essential for responsible forest management and the long-term conservation of natural resources. Functional modification of wood surfaces via azo coupling with diazonium salts offers a sustainable approach to coloration and marking. We investigate the substrate specificity and temporal dynamics of this reaction across softwood and hardwood species (oak, beech, and spruce), probing the roles of lignin, extractives, hemicellulose, and cellulose. Phenolic groups from lignin and extractives emerge as the primary reactive sites. While extractive content drives reaction kinetics in raw wood, overall coupling efficiency after their removal is strongly influenced by lignin composition—particularly the guaiacyl-to-syringyl ratio and degree of lignin condensation. Among the diazonium salts tested, Fast Black K (FB) exhibits superior performance, likely due to enhanced molecular planarity, stronger π-π stacking, and Zn²⁺ counterion effects that promote robust interactions with wood. Despite variations in salt and wood type, final coloration consistently converges towards reddish hues, as confirmed by CIELab measurements, reflecting lignin's intrinsic chromophoric properties. This study highlights the interactions between wood components, their chemistry and diazonium salt design, that offers opportunities for controlled functionalization of wood surfaces.

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木质基质中重氮盐结合和显色的分子研究

可持续的木材标记和跟踪对于负责任的森林管理和自然资源的长期养护至关重要。通过偶氮偶联与重氮盐对木材表面进行功能修饰，提供了一种可持续的着色和标记方法。我们研究了这种反应在软木和硬木物种（橡树、山毛榉和云杉）中的底物特异性和时间动力学，探讨了木质素、提取物、半纤维素和纤维素的作用。木质素和萃取物中的酚基是主要的反应位点。虽然萃取物的含量驱动了原材中的反应动力学，但去除后的整体偶联效率受到木质素组成的强烈影响，尤其是愈创木酰与丁香基的比例和木质素缩合程度。在测试的重氮盐中，Fast Black K （FB）表现出优异的性能，可能是由于增强的分子平面度，更强的π-π堆叠和Zn2+反离子效应，促进了与木材的强大相互作用。尽管盐和木材类型有所不同，但最终的颜色始终趋近于红色，正如CIELab的测量结果所证实的那样，反映了木质素固有的显色特性。这项研究强调了木材成分之间的相互作用，它们的化学和重氮盐的设计，这为木材表面的控制功能化提供了机会。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.