研究目的
To create a family of fluorescent indicators with a transition range in the neutral or basic region that could have low polarity (high lipophilicity) and a low affinity for engaging in specific intermolecular interactions in both protonation states.
研究成果
A series of four compounds were synthesized using the 7‐amino‐4‐(trifluoromethyl)coumarin backbone and their molecular structures were confirmed by several analytical techniques. The measured properties of these compounds show promise as practical fluorescent pH indicators in the pH range of 7 to 9. The designed compounds proved to have favorable characteristics related to liphophicity/solubility, show the desired spectral sensitivity to the pH of the environment, and should have limited interactions with other molecules.
研究不足
The reaction conditions for all synthesized phosphazene compounds were not optimized to obtain higher yields. The aqueous pKa values were estimated from MeCN data with standard uncertainties of 0.5 pKa units. The compounds are practically insoluble in water, limiting direct measurement in aqueous systems.
1：Experimental Design and Method Selection:
The study involved synthesizing four novel phosphazene-based fluorescent indicators using the Staudinger reaction. The molecular structures were confirmed using ATR-FT-IR, NMR, and FT-ICR high-resolution mass spectrometry. Characterization included UV-Vis absorption and fluorescence emission spectra, lipophilicity (logP) measurements, and pKa determinations in acetonitrile and biphasic (water/1-octanol) systems.
2：Sample Selection and Data Sources:
Compounds 1a to 1d were synthesized from 7-amino-4-(trifluoromethyl)coumarin and various phosphanes. Solvents included acetonitrile, toluene, and 1-octanol.
3：List of Experimental Equipment and Materials:
Equipment included UV-Vis spectrophotometers (Thermo Nicolet Evolution 300 BB, Perkin-Elmer Lambda 12/40, Agilent Cary 60), fluorometer (Horiba FluoroMax-4), FT-IR spectrometer (Thermo Scientific Nicolet 6700), mass spectrometer (Varian J-320 MS with Varian 910 FT-ICR), NMR spectrometers (Bruker AVANCE II 200, Bruker AVANCE III 700), and melting point apparatus (Gallenkamp). Chemicals included 7-amino-4-(trifluoromethyl)coumarin (Alfa Aesar), NaN3 (Riedel-de Ha?n), phosphanes (Aldrich), and solvents (Rathburn, Sigma-Aldrich).
4：Experimental Procedures and Operational Workflow:
Synthesis involved Staudinger reaction under argon atmosphere, followed by recrystallization. Characterization included spectral measurements under controlled conditions (e.g., glovebox for pKa in MeCN), lipophilicity determination by shake-flask method with HPLC, and pKa measurements using spectrophotometric titration and biphasic methods.
5：Data Analysis Methods:
Data analysis included multilinear regression for pKa determination, IFE corrections for fluorescence, and correlation analysis for aqueous pKa estimation from MeCN data.
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UV-Vis Spectrophotometer
Evolution 300 BB
Thermo Nicolet
Measurement of absorption spectra for biphasic pKa measurements and inner filter effect corrections
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UV-Vis Spectrophotometer
Lambda 12
Perkin-Elmer
Measurement of absorption spectra for pKa values in MeCN
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UV-Vis Spectrophotometer
Lambda 40
Perkin-Elmer
Measurement of absorption spectra for pKa values in MeCN
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UV-Vis Spectrophotometer
Cary 60
Agilent
Measurement of absorption spectra for pKa values in MeCN
Cary 60 UV-Vis Spectrophotometer
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FT-IR Spectrometer
Nicolet 6700
Thermo Scientific
Recording ATR-FT-IR spectra for compound characterization
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NMR Spectrometer
AVANCE II 200
Bruker
Nuclear magnetic resonance measurements
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NMR Spectrometer
AVANCE III 700
Bruker
Nuclear magnetic resonance measurements for compound characterization
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Toluene
HPLC grade
Sigma-Aldrich
Solvent for logP measurements
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1-Octanol
Chromasolv grade
Sigma-Aldrich
Solvent for logP and biphasic pKa measurements
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Fluorometer
FluoroMax-4
Horiba
Measurement of fluorescence emission spectra
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Mass Spectrometer
J-320 MS
Varian
Mass spectrometry analysis
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FT-ICR Mass Spectrometer
Varian 910
Varian
High-resolution mass spectrometry for compound verification
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Melting Point Apparatus
SG 95/09/223
Gallenkamp
Determination of melting points
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Glovebox
Unilab
MBraun
Ensuring environment free from traces of water and oxygen for pKa measurements
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Water Purification System
Milli-Q Advantage A10
Millipore
Preparation of water for experiments
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7-amino-4-(trifluoromethyl)coumarin
Alfa Aesar
Starting amine for synthesis
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NaN3
Riedel-de Ha?n
Synthesis of aryl azides
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PhPCl2
Aldrich
Starting material for synthesis of phosphanes
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Ph2PCl
Aldrich
Starting material for synthesis of phosphanes
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Pyrrolidine
Aldrich
Starting material for synthesis of phosphanes
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