An amphiphilic B,O-chelated aza-BODIPY dye: synthesis, pH-sensitivity, and aggregation behaviour in a H2O/DMSO mixed solvent.
An amphiphilic B,O-chelated aza-BODIPY dye: synthesis, pH-sensitivity, and aggregation behaviour in a H2O/DMSO mixed solvent.
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DOI：
10.1039/d1ob00746g
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发表时间：
2021-06
影响因子：
3.2
通讯作者：
Bin Lei;Hongfei Pan;Yongjie Zhang;Xiang-Kui Ren;Zhijian Chen
中科院分区：
文献类型：
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作者：
Bin Lei;Hongfei Pan;Yongjie Zhang;Xiang-Kui Ren;Zhijian Chen
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，含有疏水性十二烷氧基和亲水性四甘醇 (TEG) 链，并通过 NMR、HRMS、Vis/NIR 吸收和荧光光谱进行了表征。与常见的 BF2 螯合氮杂-BODIPY 染料相比，B,O-螯合染料 1 表现出很大程度上红移的近红外吸收和荧光光谱。向染料 1 溶液中逐渐添加三氟乙酸 (TFA) 后，在可见光/近红外吸收和荧光光谱测量中观察到明显的光谱变化。同时，肉眼观察到染料1溶液从粉红色到蓝色的颜色变化，表明染料1的pH敏感性。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的两亲性特征，它在水/DMSO（2/8，v/v）混合溶剂中自组装成J型聚集体。温度依赖性可见光/近红外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。
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.