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The Development of Benzimidazole-based Ratiometric Fluorescent Probes and Their Applications

Author: QiHaiPing
Tutor: YangXiaoFeng
School: Northwestern University
Course: Analytical Chemistry
Keywords: Benzimidazole Fluorescent probe Ratio method
CLC: O657.3
Type: Master's thesis
Year: 2010
Downloads: 235
Quote: 0
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Abstract


The fluorescence ratio method is by measuring the fluorescence intensity at two different wavelengths, with its ratio as signal parameter, thereby to determine the analysis method of the object. Fluorescence ratio signal from the light source intensity and impact of the sensitivity of the instrument, compared with traditional fluorescent probe, the ratio of fluorescent probes can improve the method's selectivity, sensitivity and dynamic range. The ratio of fluorescence probe design mechanism fluorescence resonance energy transfer, excited state intramolecular proton transfer, intramolecular charge transfer. 2 - (2 - hydroxyphenyl) benzimidazole (2 - (2-hydroxyphenyl) benzimidazole, HPBI) due to the presence of the excited state intramolecular proton transfer (excited state intramolecular proton transfer, ESIPT) process, launch dual fluorescence peaks. The ESIPT process if we modified hydroxy HPBI structure of the molecule can not effectively occur, the corresponding change in the fluorescence spectra so that HPBI. In this paper, HPBI for the parent, the hydroxyl groups in its structure as a ratio of the fluorescent probe switch, built F-, alkaline phosphatase (of alkaline phosphatase, ALP) and P2O74-selective response ratio of fluorescent probe . While article 2 - phenylbenzimidazole precursor, introduction of an aldehyde group, on the bit in the benzimidazole to produce 2 - (4 - formylphenyl) benzimidazole. The structure of compounds containing electron donating group benzimidazolyl group and a strong electron withdrawing group aldehyde, by ultraviolet excitation, can effectively intramolecular charge transfer mechanism (intramolecular CHARGE Transfer, ICT), thus, 2 - (4 - the aldehyde phenyl) benzimidazole launch dual fluorescence peaks. If we make use of the aldehyde group in the structure of this compound and HSO3-reaction, the molecule electron-withdrawing sexuality reduced, resulting in the ICT process can not occur, so that the fluorescence characteristics of the system change. Therefore, 2 - (4 - formylphenyl) benzimidazole to achieve a ratio of HSO3-type response. This thesis consists of the following five parts: The first chapter. Ratio fluorescent probe design mechanism, based on the idea put forward in this paper. Chapter II of the F-ratio determination based ESIPT mechanism fluorescent probes. Hydroxyl in this chapter through HPBI molecular structure of protection / deprotection response to the design and synthesis of the determination of the ratio of the F-type fluorescent probe 1. Compound 1 can not occur ESIPT process, only a single fluorescence peak at 360 nm and emission. The F-, the structure of Compound 1 in TBS functional groups in an aqueous solution of DMF was added by F-selective cutting, thereby restoring the precursor of fluorescent molecules HPBI the ESIPT process, resulting in the reaction system was decreased fluorescence emission at 360 nm, while at 454 nm The fluorescence emission enhanced. Before and after using the reaction system at 360 nm and at 454 nm the fluorescence intensity ratios (I454/I360) the content of the F-quantitative. Chapter fluorescence ratio method for the determination of the properties of the ALP. Chapter by the hydroxyl-reactive in phosphorus oxychloride HPBI molecule, and then hydrolyzed to generate a fluorescent probe molecules 2. Compound 2 blocking ESIPT process normal, single fluorescence peak at 363 nm emission. Added to a solution of 2 of ALP, ALP optionally of the two molecules in the hydrolysis of the phosphate group, to restore the original precursor fluorescence molecular structure HPBI of so System ESIPT process effectively occur, resulting in the system at 430 nm appeared a fluorescence emission peak. With ALP concentration increases, the reaction system was gradually increased in the fluorescence emission intensity of the 430nm at, while the 363 nm fluorescence emission is gradually weakened. The fluorescence intensity of the system before and after the use of the reaction ratio I430/I363 quantitative analysis of the ALP. The method of determination of ALP linear ceiling to 0.050 UmL-1, a detection limit of 0.0013 U-mL-1. Chapter synchronous fluorescence method for the determination of the nature of the study of pyrophosphate. Chapter to HPBI precursor, and Zn2 complexation, the reaction of metal complex (Compound 3). Due to hydroxyl HPBI molecular hydrogen is bound to live, therefore compound 3 can not effectively ESIPT process occurs, the fluorescence emission wavelength of 418 nm. When added to the system after P2O74-, P2O74-the phosphoric acid group can effectively compete with HPBI Zn2 ions, so that the 3 dissociation ESIPT process restored HPBI molecule itself. However, compound 3 and reaction product HPBI, the maximum emission wavelength (454 nm) in the phase difference closer, both the fluorescence emission spectra easily overlap, therefore experiments considered synchronous fluorescence method. HPBI exists another fluorescence emission peak at 364 nm, and its Stokes shift to Δλ and 3 emission peaks from very similar experiment using synchronous fluorescence spectrometry and selected Δλ of 40 nm can be HPBI at 364 nm the fluorescence emission peak of the fluorescence emission peak and the compound 3 is very good separate areas. P2O74-3 solution was added, the reaction system at 364 nm the fluorescence emission enhanced fluorescence emission at 418 nm at the same time weaken. Based on this principle, this chapter synchronous fluorescence determination of P2O74-ratio method. Chapter characterization of HSO3-ratio type the synthesis and properties of fluorescent probes. This chapter designed and synthesized a new ratio-type fluorescent probes determination of HSO3-4. The compound 4 due to the presence of intramolecular charge transfer process, respectively, at 368 nm and 498 nm emission fluorescence peaks. When the HSO3-in compound 4, 4-aldehyde and HSO3-nucleophilic addition reaction occurs, thereby blocking the normal of the ICT process, so that 4 at 368 nm the fluorescence emission enhanced, while 498 nm at The fluorescence intensity, and the intensity ratio of the two fluorescence peaks (I368/I498) HSO3-linear relationship between the concentration in the range of 2 × 10-6-2.0 × 10-4mol L-1. The probe fast the HSO3-response speed, and good selectivity.

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CLC: > Mathematical sciences and chemical > Chemistry > Analytical Chemistry > Instrument analysis ( physics and physical chemistry ) > Photochemical analysis ( spectral analysis method)
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