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Pentiptycene derivative as well as preparation method and application thereof in polyamine detection

A derivative, pentastyrene technology, applied in the field of compound detection, can solve the problems of insufficient detection sensitivity of fluorescent probes and small degree of fluorescence change

Inactive Publication Date: 2019-06-04
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the blue and green colors are relatively close and the degree of fluorescence change is small, the detection sensitivity of this fluorescent probe is not strong enough

Method used

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  • Pentiptycene derivative as well as preparation method and application thereof in polyamine detection
  • Pentiptycene derivative as well as preparation method and application thereof in polyamine detection
  • Pentiptycene derivative as well as preparation method and application thereof in polyamine detection

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1 - the synthesis of formula I compound

[0059] In this embodiment, a representative compound of formula I in which n is 3 and R is H is synthesized, represented by the code SSS1.

[0060] The synthetic route of the formula I compound SSS1 of the present embodiment is as follows figure 1 and figure 2 shown. Except for the starting compound 1 shown in the following formula 1, other compounds used in the synthesis are commercially available. The synthetic method of starting compound 1 shown in following formula 1 is in literature Satrijo A., Kooi S., Swager T., Enhanced Luminescence from Emissive Defects in Aggregated Conjugated Polymers, Macromolecules 2007,40,8833-8841 and LehnherrD., McDonald R ., reported in Tykwinski R. Exploring Electronically Polarized Pentacenes Org. Lett. 2008, 10, 4163-4166, the relevant contents of these two documents are incorporated herein by reference.

[0061] (1) Synthesis of intermediate compound 1'

[0062] figure 1 It...

Embodiment 2

[0088] Embodiment 2 - the synthesis of formula I compound

[0089] This embodiment synthesizes other representative compounds of formula I, respectively represented by codes SSS2, SSS3 and SSS4, wherein respectively, n is 1, R is H, or n is 1, R is OMe, or n is 3, R for OMe. The method of synthesis is analogous to Example 1, with the exception that a compound of formula 2" with a corresponding value of n and a compound of formula 5" with a corresponding R group are used. The structural identification data of the final product are listed below:

[0090] SSS2: n=1, R=H; pale yellow powdery solid (33.6mg, 0.024mmol, 80%), m.p.>300°C. 1 HNMR(400MHz,MeOD)δ8.00(s,2H),7.85(s,1H),7.73–7.61(m,2H),7.36–7.19(m,4H),7.09–6.97(m,14H),6.97 –6.84(m,7H),6.84–6.70(m,4H),5.92(s,4H),5.40(s,2H),5.13(s,2H),3.56(q,J=7.0Hz,4H), 3.35 (q, J=7.0Hz, 4H), 1.33–1.21 (m, 6H), 1.21–1.07 (m, 6H). 13 CNMR (100MHz, MeOD) δ169.0, 168.1, 160.0, 158.8, 154.0, 147.3, 146.0, 145.4, 145.3, 145.2, 144.4, 144.1, 1...

Embodiment 3

[0093] Embodiment 3 - the characterization of formula I compound SSS1

[0094] (1) The photophysical spectrogram of formula I compound SSS1

[0095] SSS1 was dissolved in 1% methanol / water solution to prepare a solution with a concentration of 10 μM. Measure its UV-Vis absorption spectrum with a UV-Vis spectrophotometer (Shimadzu Corporation UV-2600 type), the results are as follows: image 3 shown in the left figure. The two curves in the left figure are the ultraviolet absorption spectra of the SSS-1 solution alone and the SSS-1 solution after adding 1 equivalent of Spm. After adding Spm, there is an obvious red shift, indicating that there is an interaction between Spm and SSS-1. Use this solution in fluorescence spectrometer (Japan Shimadzu RF-5301), take 480nm as emission wavelength, measure the excitation spectrum of SSS1, the result is as follows image 3 shown in the figure on the right. It can be seen from the figure on the right that under the excitation waveleng...

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Abstract

The invention relates to a pentiptycene derivative represented by formula I, n is 1 or 3, and R is H or OMe. The invention also relates to a preparation method of the pentiptycene derivative and a preparation method, application thereof in polyamine compound detection, a fluorescent sensor comprising the pentiptycene derivative represented by the formula I and a method for detecting polyamine compounds. The polyamine compounds are particularly putrescine, cadaverine, spermidine and spermine. The pentiptycene derivative shown in the formula I does not emit light basically in a free state, and emits fluorescent light in the presence of the polyamine compounds. The pentiptycene derivative has an aromatic group comprising a donor-pi-receptor manner and a fluorescent group having an aggregation-induced luminescence effect, so that the fluorescence intensity is very obvious. Therefore, the pentiptycene derivative represented by the formula I can be used as a fluorescent probe of the polyamine compounds, especially can be used for detecting biological polyamine compounds in an animal and a plant body, and can be used as an effective means for researching a biological model and detecting life metabolites.

Description

technical field [0001] The invention relates to the technical field of compound detection, in particular to a pentastyrene derivative, a preparation method of the pentastyrene derivative and the use of the pentastyrene derivative in the detection of polyamine compounds. Background technique [0002] Polyamine compounds are a class of compounds containing two or more amino groups, which are cationic aliphatic amines with multiple charges. Polyamine compounds widely exist in animals and plants, also known as biological polyamine (biogenic polyamine), mainly including putresine (Put), cadaverine (cadaverine, Cad), spermidine (spermidine, Spd) and spermine ( spermine, Spm). The concentration of polyamine compounds in normal mammalian cells is generally maintained at the millimolar level. The physiological function of polyamine compounds mainly lies in the electrostatic interaction with DNA, RNA, protein and other negatively charged biomacromolecules, thereby changing the struc...

Claims

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Application Information

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IPC IPC(8): C07D401/12C09K11/06G01N21/64
Inventor 李志成黄均荣李庆
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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