Supporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood

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1 Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang* State Key Laboratory of Analytical Chemistry for Life Science, Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 9, China. Phone: (Y.Q) and (D.J) and (D.J). Synthesis procedure and characterization of azabdpba S. Characterization of azabdph S. Titration curve of azabdpba to hydrogen peroxide S 4. Optimization of the reaction time for stable fluorescence signals S4 5. Fluorescence spectra of azabdpba to fructose S5 6. Interference of saccharides on the glucose detection S6 7. Fluorescence spectra of azabdpba for glucose in whole blood S7 8. Fluorescence spectra of azabdpba in glucose spiked plasma S8 9. Glucose calibration curve in whole blood S9. Optimization of the optode membrane thickness S

2 . Synthesis procedure and characterization of azabdpba -(4-bromidephenyl)--phenylpropenone (compound ) To a solution of 4-bromide acetophenone (99.4 g, mol, eq) in ethanol was added aqueous sodium hydroxide (.44 L,.5 M). Benzaldehyde (6. g, mol, eq) in ethanol was added dropwise at room temperature. During the course of the reaction, the product precipitated from the reaction mixture. After h, the reaction mixture was filtrated off and the resulting solid was washed with water to remove the excess sodium hydroxide. The crude product was recrystallized in ethanol and washed with ethanol to yield the product as a light yellow solid (9.8 g, 8% yield). H NMR (4 MHz, CDCl ) δ (ppm): 7.9 (d, H, J=.8Hz), 7.84 (d, H, J=5.68Hz), 7.67 (d, 4H, J=4.6 Hz), 7.65 (s, H), 7.47 (t, H, J=5.7 Hz) -(4-Bromidephenyl)-4-nitro--phenylbutan--one (compound 4) A solution of -(4-bromide)--phenylpropenone (6 g,.75 mol, eq) in methanol ( L) was treated with diethylamine (74.9 g,.75 mol,5 eq) and nitromethane (9.5 g,.75 mol, 5 eq) and heated under reflux for h. The solution was concentrated to about ml, cooled and acidified with 4 M HCl to the ph of -4. After that, the solution was extracted with dichloromethane and washed with saturated sodium chloride. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The yellow oil residue was stirred in cold methanol, filtered and washed with methanol, to give the product 4 (9 g, 77% yield) as solid by recrystallization with methanol. [5-(4-Boromidephenyl)--phenyl-H-pyrrol--yl]-[5-(4-Bromidephenyl)--phenylpyrrol- -ylidene]amine (compound 5) Compound 4 ( g,.9 mol, eq) and ammonium acetate(5 g,.65 mol, 5 eq) in ethanol (.5 L) were heated under reflux for h until the complete consumption of compound 4, as confirmed by TLC. The purification using column chromatography on silica eluting with THF: PE (.5:) gave the solid. The isolated solid was then filtered and washed with cold methanol and petroleum ether to yield the product 5 as a blue-black solid (6.4 g, 45% yield). H NMR (4 MHz, CDCl ) δ (ppm): 8.5 (d, 4H, J=6.96Hz), 7.8 (d, 4H, J=8.Hz), 7.69 (d, 4H, J= 8. Hz), 7.44 (d, 6H, J=7.4 Hz), 7.8 (s, H). [5-(4-Pinacolatodiboranephenyl)--phenyl-H-pyrrol--yl]-[5-(4-Pinacolatodiboranephe nyl)--phenylpyrrol--ylidene]amine (compound 6)

3 Compound 5 (.8 g, 8 mmol, eq), bis(pinacolato)diboron (6 g, 6 mmol,.5 eq), ammonium acetate ( 5. g, 65.4 mmol, 9 eq) and Pd(dppf)Cl (6 g, 7. mmol,.4 eq) were refluxed in 5mL THF under a N -atmosphere for h. The crude product was purified by silica gel chromatography (PE: THF=:) to afford compound 6 as purple solid. BF Chelate of [5-(4-Pinacolatodiboranephenyl)--phenyl-H-pyrrol--yl]- [5-(4-Pinacolatodiboranephenyl)--Phenylpyrrol--ylidend]amine (compound 7) Compound 6 was dissolved in dry CH Cl, followed by the addition of N,N-diisopropylethylamine (DIPEA) (.5 ml, 75 mmol, eq) in N protected atmosphere for about h at room temperature. Then, BF Et O (5 mml,.5 mmol, 5 eq) was added. After stirring for another 4 hours, the reaction mixture was washed with water, dried and the solvent evaporated. Silica column chromatography (PE: THF=:) of the residue yielded crude compound 7 as purple powder. azabdpba (compound 8) Compound 7 ( g,. mmol, eq) and diethanolamine (9 mg,.8 mmol,. eq) were added in 5 ml THF and stirred at room temperature for.5 hour. The dark purple precipitate was collected and washed with another 5 ml THF, and then added to the solution of HCl (. M, 56 ml). After all solid dissolved for h, the solution was extracted using diethyl ether followed by purification on silica gel chromatography (CH OH: CH Cl = :). Compound 8 as purple solid was obtained in 7% yield. HNMR (4 MHz, DMSO) δ (ppm): 8.9 (s, 4H), 8.9 (d, 4H, J=7.8), 8.9 (d, 4H), 7.94 (d, 4H), 7.64 (s, H), (m, 6H). C NMR (4 MHz, DMSO): 59.49, 45.5, 4.8, 4.6,.6,.,., 9.7, 9., 8.9,.84. HRMS (EI): Calcd for C H 4 B F N O 4, 585.; found, m/z 586. (+ H)

4 4

5 T: FTMS + p ESI Full ms [4.-8.] Relative Abundance m/z Figure S. H NMR (4 MHz, DMSO-d 6 ), C NMR ( Hz, DMSO-d 6 ) and mass spectra (acetonitrile) of azabdpba.. Characterization of azabdph T: FTMS + p ESI Full ms [ ] Relative Abundance m/z Figure S. Mass spectra of azabdph. 5

6 . Titration curve of azabdpba to hydrogen peroxide 4 I 74/ logch O Figure S. The titration curve relation (I 74nm /I 68 nm ) of azabdpba ( µm) as a function of the H O concentrations. 4. Optimization of the reaction time for stable fluorescence signals I68/ Time / min Figure S4. Kinetic response of azabdpba toward mm PBS buffered glucose solution at reaction temperature of 5 ( ), 8 ( ), 5 ( ), respectively. 6

7 5. Fluorescence spectra of azabdpba to fructose 8 6 Increasing fructose concentration Intensity Wavelength / nm Figure S5. Fluorescence spectra of µm azabdpba to different fructose concentration from µm to mm. 6. Interfere of saccharide on the glucose detection I74/68 4 Glucose+GOx Glucose+Fructose +GOx Glucose+Galactose+GOx Glucose+Sorbitol+GOx Selectivity Glucose+Sucrose+GOx Figure S6. The selectivity of azabdpba ( µm) for glucose ( mm) in the prescence of other competitive saccharides ( mm). 7

8 7. Fluorescence spectra of azabdpba for glucose in whole blood RFI Wavelength / nm Figure S7. Fluorescence spectra of µm azabdpba in glucose spiked whole blood. 8. Fluorescence spectra of azabdpba in glucose spiked plasma RFI I74/68 R = logcglucose Wavelength / nm Figure S8. Main: Fluorescence spectra of µm azabdpba in glucose spiked plasma. Inset: The linear glucose calibration curve in plasma. 8

9 9. Glucose calibration curve in whole blood I76/686 R = logcglucose Figure S9. The linear glucose calibration curve of azabdpba ( µm) in whole blood (I 76nm /I 686nm ).. Optimization of the optode membrane thickness 8 Response time / min Membrane thickness / mm Figure S. The effect of membrane thickness on the response time of azabdpba-based optode., 4, 8 and µl cocktails were dropped on the plate, respectively. The thickness was estimated based on the cocktail volume and plate area. 9

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