Perylene diimide-rhodamine fluorescent probe, and preparation method and application thereof
A perylene diimide and fluorescent probe technology, applied in the field of fluorescent probes, can solve problems such as strong π-π interaction, application limitations of perylene diimide fluorescent compounds, poor solubility, etc., to achieve improved solubility, good Good solubility and stability
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Embodiment 1
[0029] Preparation of perylenediimide-rhodamine fluorescent probe Rh-PDI
[0030] Rhodamine-Ethylamine (Rh-NH 2 ) was prepared according to the literature method (Xuan Zhang, Yasuhiro Shiraishi, Takayuki Hirai.Cu(II)-selective green fluorescence of a rhodamine-diacetic acid conjugate.Organic Letters, 2007,9(24),5040), the specific process is as follows: nitrogen protection Next, rhodamine B and ethylenediamine were refluxed in ethanol for 15h to obtain Rh-NH 2 .
[0031] 1,7-bis(4-tert-butylphenyloxy)-3,4,9,10-perylenetetracarboxylic dianhydride (PTA) was prepared by the following steps according to the literature method:
[0032] Step 1. Prepare 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride according to literature method (Qiuli Zhao, Shuang Zhang, Yi Liu, Ju Mei, Sijie Chen, Ping Lu, Anjun Qin, Yuguang Ma, Jingzhi Sun, Benzhong Tang. Tetraphenylethenyl-modified perylene bisimide: aggregation-induced red emission, electrochemical properties and ordered microstruc...
Embodiment 2
[0047] UV Absorption and Fluorescence Properties of Perylene Diimide-Rhodamine Probe Rh-PDI in THF
[0048] Rh-PDI in tetrahydrofuran (the concentration of Rh-PDI is 10 -5 mol / L) UV-Vis absorption spectrum is a bimodal structure, the maximum absorption peaks are 500 and 530nm respectively.
[0049] The maximum wavelength of the fluorescence spectrum of Rh-PDI in tetrahydrofuran is located at 585nm, and the fluorescence is very weak. At this time, the rhodamine fluorophore in Rh-PDI is in the closed-loop "off" state and has no fluorescence; while the fluorescence of the perylene fluorophore in Rh-PDI is quenched due to photoinduced electron transfer, so Rh-PDI is very fluorescent in THF. weak.
Embodiment 3
[0051] Sensitive Response of Perylene Diimide-Rhodamine Probe Rh-PDI to pH
[0052] figure 1 It is the fluorescence spectrum of Rh-PDI in water / tetrahydrofuran mixed solution with pH response, wherein the concentration of Rh-PDI is 10 -5 mol / L. When the pH is greater than 2.2, the fluorescence of Rh-PDI is quenched in the water / THF mixed solution, and the perylenediimide-rhodamine fluorophore is in the "off" state. When the pH value is less than 2.2, under strong acidic conditions, Rh-PDI has a strong fluorescence in water / tetrahydrofuran mixed solution. From pH 2.17 to 1.38, the fluorescence of Rh-PDI increases rapidly, and the maximum emission peak is at 552nm, and the emission at 580nm The peak shoulder gradually increases. At this time, the perylenediimide-rhodamine fluorophore is in the "on" state. Show that Rh-PDI is a sensitive pH-responsive fluorescent probe.
[0053] With the pH response, the color of the probe molecules changed significantly under sunlight, and ...
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