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

CN104151326AInactive Publication Date: 2014-11-19SOUTHEAST UNIV
2 Cites 17 Cited by

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2014-11-19
Estimated Expiration
Not applicable · inactive patent

Smart Images

  • Figure 1
    Figure 1
  • Figure 2
    Figure 2
  • Figure 3
    Figure 3
Patent Text Reader

Abstract

The invention discloses a perylene diimide-rhodamine fluorescent probe, and a preparation method and an application thereof. The fluorescent probe has the following structural formula. The invention also discloses a preparation method of the fluorescent probe and an application thereof. The perylene diimide-rhodamine fluorescent probe provided by the invention has good solubility and a fluorescent probe property of good sensitivity. The fluorescent probe can be used as a near-infrared fluorescence emission sensitive pH fluorescent probe and a mercury ion fluorescent probe. The fluorescent probe has important application values in the fields of fluorescent switch and sensor, fluorescent probe, bio-marker and fluorescent imaging, organic light-emitting device, and the like.
Need to check novelty before this filing date? Find Prior Art

Description

technical field

[0001] The invention relates to the technical field of fluorescent probes, in particular to a perylene diimide-rhodamine fluorescent probe and its preparation method and application. Background technique

[0002] Perylene diimide has strong near-infrared emission, high quantum efficiency, and good fluorescence performance, but its large π conjugated planar stacking, strong intermolecular π-π interaction, and poor solubility make perylene diimide The application of amine fluorescent compounds has been greatly limited.

[0003] By modifying the substituents at the bay and amide positions of the perylene ring, improving the solubility of perylene derivatives and regulating the fluorescence properties of the molecules, the research and development of highly efficient and near-infrared emitting perylene diimide fluorescent probes has attracted extensive attention. Such materials can be used to prepare high-efficiency light-emitting devices, fluorescent molecular ...

Examples

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 ...