An amphiphilic B,O-chelated aza-BODIPY dye: synthesis, pH-sensitivity, and aggregation behaviour in a H2O/DMSO mixed solvent,Organic & Biomolecular Chemistry

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An amphiphilic B,O-chelated aza-BODIPY dye: synthesis, pH-sensitivity, and aggregation behaviour in a H2O/DMSO mixed solvent
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-6-16 , DOI: 10.1039/d1ob00746g
Bin Lei ₁ , Hongfei Pan ₁ , Yongjie Zhang ₁ , Xiang-Kui Ren ₂ , Zhijian Chen ₂

Affiliation

A novel amphiphilic B,O-chelated azadipyrromethene (aza-BODIPY) dye, containing hydrophobic dodecyloxy groups and hydrophilic tetraethylene glycol (TEG) chains, was synthesized and characterized by NMR, HRMS, Vis/NIR absorption and fluorescence spectroscopy. The B,O-chelated dye 1 exhibited largely bathochromically shifted NIR absorption and fluorescence spectra in comparison with common BF₂-chelated aza-BODIPY dyes. Upon gradual addition of trifluoroacetic acid (TFA) to the dye 1 solution, obvious spectral changes were observed in Vis/NIR absorption and fluorescence spectroscopy measurements. Meanwhile, the colour change of the dye 1 solution from pink to blue was noticeable by the naked eye, indicating the pH-sensitivity of dye 1. The pH-sensitivity of dye 1 under acidic conditions could be ascribed to the formation of dye species 2·H⁺. Furthermore, owing to the amphiphilic feature of dye 1, it self-assembled into J-type aggregates in a mixed solvent of water/DMSO (2/8, v/v). Temperature-dependent Vis/NIR spectroscopic studies revealed a cooperative aggregation process of dye 1 and a nanowire-like morphology of the nanoaggregates was observed by AFM.

中文翻译：

一种两亲性 B、O 螯合的 aza-BODIPY 染料：H2O/DMSO 混合溶剂中的合成、pH 敏感性和聚集行为

合成了一种新型两亲性 B,O-螯合氮杂二吡咯亚甲基 (aza-BODIPY) 染料，该染料含有疏水性十二烷氧基和亲水性四乙二醇 (TEG) 链，并通过 NMR、HRMS、Vis/NIR 吸收和荧光光谱对其进行了表征。_{与常见的 BF 2}螯合 aza-BODIPY 染料相比， B,O 螯合染料1表现出较大的红移近红外吸收和荧光光谱。在染料1溶液中逐渐添加三氟乙酸 (TFA) 后，在 Vis/NIR 吸收和荧光光谱测量中观察到明显的光谱变化。同时，染料1溶液从粉红色到蓝色的颜色变化肉眼可见，表明染料的 pH 敏感性1 . 染料1在酸性条件下的 pH 敏感性可归因于染料物种2·H ⁺的形成。此外，由于染料1的两亲特性，它在水/DMSO（2/8，v/v）混合溶剂中自组装成J型聚集体。温度依赖性 Vis/NIR 光谱研究揭示了染料1的协同聚集过程，并且通过 AFM 观察到纳米聚集体的纳米线状形态。

更新日期：2021-06-23

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