Reversible manipulation of organic dye aggregation through acyclic cucurbit[n]uril-based host-guest complexation

IF 2.3 4区化学 Q2 Agricultural and Biological Sciences

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2023-11-15 DOI:10.1007/s10847-023-01209-x

Wen-Chang Peng, Hui Wang, Dan-Wei Zhang, Zhan-Ting Li, Da Ma

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Abstract

We use a highly water-soluble acyclic cucurbit[n]uril ACB-01 that bears eight carboxylate groups. ACB-01 has excellent solubility in water and high affinity to the cyanine dyes pseudoisocyanine (PIC) and pinacyanol (PIN) to afford 1:1 complexes. The complexation has been studied by UV–vis absorption, fluorescence and nuclear magnetic resonance (NMR) spectroscopy, and the binding constants (K_a) are determined to be (1.54 ± 0.15) × 10⁶ M⁻¹ and (6.09 ± 0.82) × 10⁵ M⁻¹, respectively. This complexation leads to the inhibition of the J-aggregation of PIC and H-aggregation of PIN. However, competitive guests methyl viologen and 1-adamantanamine hydrochloride can recover their respective J- and H-aggregation due to more stable complexation occurs between them and ACB-01. Thus, we have established a new method of reversibly controlling dye aggregation by regulating the concentration of ACB-01 and competitive guests.

Graphical abstract

Abstract Image

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通过无环葫芦[n]脲基主-客体络合的可逆操作有机染料聚集

我们使用了一种高度水溶性的无环葫芦[n]uril ACB-01，它含有8个羧酸基。ACB-01在水中具有良好的溶解度，对菁染料假异氰酸(PIC)和蒎酸醇(PIN)具有很高的亲和力，可形成1:1的配合物。通过紫外-可见吸收、荧光和核磁共振(NMR)光谱对其络合作用进行了研究，确定了其结合常数Ka分别为(1.54±0.15)× 106 M−1和(6.09±0.82)× 105 M−1。这种络合作用抑制了PIC的j聚集和PIN的h聚集。而竞争客体紫紫甲基和1-金刚烷胺盐酸盐由于与ACB-01发生更稳定的络合作用，可以恢复各自的J-和h -聚集。因此，我们建立了一种通过调节ACB-01和竞争客体的浓度来可逆控制染料聚集的新方法。图形抽象

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry 化学-化学综合

CiteScore

3.30

自引率

8.70%

发文量

审稿时长

3-8 weeks

期刊介绍： The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.