Synthesis of rhodamine B amine derivatives with improved light resistance and its application in thermochromic materials

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2024-11-06 DOI:10.1016/j.dyepig.2024.112529

Yu Guan, Weize Wu, Jing Su, Liping Zhang

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Abstract

Rhodamine B (RhB) is a widely utilized xanthene dye known for its strong fluorescence, high quantum yield, bright color, and versatility in various applications. However, RhB type dyes face significant limitations due to their susceptibility to photodegradation. Herein, four RhB amine derivatives (RhB-1, RhB-2, RhB-3, and RhB-4) were synthesized to improve the light resistance through functionalization of the 4′ position of the carboxyphenyl ring with acrylamide, butylamine, octylamine, and cyclohexanamine, respectively. The mechanism of improving light resistance was analyzed. The results show that the derivatives demonstrated significantly enhanced light resistance compared to RhB, with the ability to form supramolecular structures including dimers and aggregates that protect against UV degradation. Light resistance for RhB-1 was significantly improved with increasing concentration as the photodegradation efficacy drops from 84.8 % (1.5 × 10⁻⁵ mol/L) to 10 % (2.0 × 10⁻⁴ mol/L), due to the dominant changes from monomers to J-dimers to H-aggregates. When incorporated into three-component thermochromic systems, the derivatives not only improved the light resistance with double duration of UV irradiation but also expanded the range of color change temperatures. This work advances the development of RhB derivatives with superior optical properties and durability, enhancing its applicability in environments requiring prolonged exposure to light.

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具有更好耐光性的罗丹明 B 氨基衍生物的合成及其在热致变色材料中的应用

罗丹明 B（RhB）是一种广泛使用的氧杂蒽染料，因其荧光强、量子产率高、颜色鲜艳和用途广泛而闻名。然而，由于容易发生光降解，RhB 型染料面临着很大的局限性。本文合成了四种 RhB 氨基衍生物（RhB-1、RhB-2、RhB-3 和 RhB-4），分别通过丙烯酰胺、丁胺、辛胺和环己胺对羧基苯基环的 4′ 位进行官能化来提高其耐光性。分析了提高耐光性的机理。结果表明，与 RhB 相比，这些衍生物的耐光性明显增强，能够形成包括二聚体和聚集体在内的超分子结构，从而防止紫外线降解。随着浓度的增加，RhB-1 的耐光性显著提高，光降解效率从 84.8 %（1.5 × 10-5 mol/L）降至 10 %（2.0 × 10-4 mol/L），这是由于从单体到 J-二聚体再到 H-聚集体的主导变化所致。当这些衍生物加入到三组分热致变色体系中时，不仅在双倍紫外线照射时间内提高了耐光性，还扩大了变色温度的范围。这项工作推动了具有优异光学特性和耐久性的 RhB 衍生物的发展，提高了其在需要长时间暴露于光的环境中的适用性。

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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.