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    Optical Glucose Sensing Using Ethanolamine-Polyborate Complexes

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    Optical Glucose Sensing Using Ethanolamine-Polyborate Complexes

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    Optical Glucose Sensing Using Ethanolamine-Polyborate Complexes

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    Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.

    This journal is © The Royal Society of Chemistry 2018

    Optical glucose sensing using ethanolamine-polyborate complexes

    C. Toncellia, *, R. Innocenti Malinia, D. Jankowskab, F. Spanoa, H. Cölfenc, K. Maniura-


    Weberb, R.M. Rossia and L.F. Boesela, *

    aEmpa, Swiss Federal Laboratories for Materials Science and Technology, Laboratory for Biomimetic
    Membranes and Textiles, Lerchenfeldstrasse 5, CH-9014 St. Gallen, Switzerland.
    bEmpa, Swiss Federal Laboratories for Materials Science and Technology, Biointerfaces, Lerchenfeldstrasse 5,
    CH-9014 St. Gallen, Switzerland.
    cMax-Planck-Institut für Kolloid- und Grenzflächenforschung, Kolloidchemie, Forschungscampus Golm, 14424
    Potsdam, Germany

    Table of Contents:

    Figure S-1. Kinetic of B-MEA B:N 1:5 monitored by fluorescence measurements


    Figure S-2. Fluorescence emission of B:MEA B:N 1:5 at different concentrations in weight
    Figure S-3. Fluorescence emission of three different batches of B:MEA B:N 1:5
    Figure S-4. Fluorescence image of B-MEA B:N 1:5 in the solid (left) and in the liquid (right)
    state upon exposure at a wavelength of 365 nm.
    Figure S-5. UV-Vis measurement of B-MEA B:N 1:5.
    Figure S-6. Naming convention for atoms present in ethanolamine and borates species.
    Figure S-7. Example of structures found in solution for the different complexes analysed.
    Figure S-8. Variation in the optical response at 0 mM (F0) and at 10 mM (F) by using three
    different pH values (i.e. 6.2, 6.8 and 7.4).
    Figure S-9. Response time of the sensor towards glucose in AWE. Conditions: B-MEA B:N
    1:5 (4 wt.-%), pH 6.8.
    Figure S-10. Comparison of the response of the sensor towards glucose and two other 1,2-diols
    (fructose and lactose). B-MEA B:N 1:5 (4 wt.-%), pH 6.8.
    Table S-1. Geometrical measurements of the interaction between borates and ethanolamine in
    solution.
    Table S-2. Geometrical measurements of the interaction between borates and ethanolamine in
    vacuum.
    Figure S-1. Fluorescence emission of B:MEA B:N 1:5 at a concentration of 0.20 mg ml-1 with
    different reaction time (excitation wavelength 380 nm).

    Figure S-2. Fluorescence emission of B-MEA B:N 1:5 at different concentration (expressed as
    w/v %) (excitation wavelength 380 nm)
    Figure S-3. Fluorescence emission of three different batches of B-MEA B:N 1:5 (reaction time
    230 min, excitation wavelength 380 nm)

    Figure S-4. Fluorescence image of B-MEA B:N 1:5 in the solid (left) and in the liquid (right)
    state upon exposure at a wavelength of 365 nm.
    Absorbance (a.u.)

    0
    250 300 350 400 450 500 550
    Wavelength (nm)
    Figure S-5. UV-Vis measurement of B-MEA B:N 1:5
    Figure S-6. Naming convention for atoms present in ethanolamine and borates species. The
    carbons atoms on the ethanolamine are defined using two numbers because systems with two
    ethanolamines were analysed. Then the first number defines the ethanolamine being measured
    and the second one differentiates the carbon in the backbone.
    Figure S-7. Example of structures found in solution for the different complexes analysed. a) B-
    MEA_1, b) B-MEA_2, c) B-MEA_3 and d) B-MEA_4.

    1.5
    F/F0

    0.5

    0
    6.2 pH6.8 7.4

    Figure S-8. Variation in the optical response at 0 mM (F0) and at 10 mM (F) by using three
    different pH values (i.e. 6.2, 6.8 and 7.4).
    45

    40

    35

    30
    PL intensity (a.u.)

    25

    20

    15 0 mM
    2 mM
    10
    4 mM

    5 8 mM

    0
    0 10 20 30 40 50 60 70

    t (min)

    Figure S-9. Response time of the sensor towards glucose in AWE. Conditions: B-MEA B:N
    1:5 (4 wt.-%), pH 6.8.

    1.8

    1.6

    1.4
    Relative PL Intensity

    1.2

    1
    Glucose
    0.8 Fructose
    Lactose
    0.6

    0.4

    0.2

    0
    0 1 2 3 4 5 6 7 8 9

    Concentration (mM)

    Figure S-10. Comparison of the response of the sensor towards glucose and two other 1,2-
    diols (fructose and lactose) in PBS. B-MEA B:N 1:5 (4 wt.-%), pH 6.8.
    Table S-1. Geometrical measurements of the interaction between borates and ethanolamine in
    solution. The measures were done on different configurations only if considerably different
    conformations were observed. B: single boroxole ring, B2: double boroxole ring, MEA:
    monoethanolamine and 2MEA: two monoethanolamines.

    B-MEA_1 B_MEA_2 B_MEA_3 B-MEA_4

    Distances (Å)

    N-Ob 3.3 ± 0.2 3.7 ± 0.1 3.4 ± 0.2 3.1 ± 0.1

    N-Obh 3.0 ± 0.1 3.3 ± 0.2 - 3.3 ± 0.3

    C11-Obh 4.0 ± 0.1 3.6 ± 0.1 - 3.6 ± 0.2

    C11-Ob 3.5 ± 0.1 3.8 ± 0.1 4.0 ± 0.1 3.5 ± 0.1

    C12-Ob - 3.8 ± 0.1 - 3.6 ± 0.1

    C12-Obh - 3.7 ± 0.1 - 3.5 ± 0.1

    Angles (degrees)

    N-Hn-Ob 138 ± 10 112 ± 7 146 ± 10 143 ± 2

    N-Hn-Obh 130 ± 27 138 ± 12 - 128 ± 19

    C11-Hc-Obh 142 ± 11 129 ± 15 - 135 ± 26

    C11-Hc-Ob 121 ± 8 123 ± 11 138 ± 12 128 ± 6

    C12-Hc-Ob - 119 ± 14 - 144 ± 20

    C12-Hc-Obh - 107 ± 5 - 136 ± 6


    Table S-2. Geometrical measurements of the interaction between borates and ethanolamine in
    vacuum. The measures were done on different configurations only if considerably different
    conformations were observed. B: single boroxole ring, B2: double boroxole ring, MEA:
    monoethanolamine and 2MEA: two monoethanolamines.

    B-MEA_1 B-MEA_2 B-MEA_3 B-MEA

    Distances (Å)

    N-Ob 3.0 ± 0.1 3.7 ± 0.1 2.8 ± 0.4 2.8 ± 0.1

    N-Obh 2.8 ± 0.1 2.9 ± 0.1 3.7 ± 0.2 3.3 ± 0.5

    C11-Obh 3.9 ± 0.1 3.8 ± 0.3 4.0 ± 0.1 3.9 ± 0.2

    C11-Ob 3.4 ± 0.1 3.4 ± 0.1 3.6 ± 0.2 3.6 ± 0.1

    C12-Ob - - - 3.5 ± 0.1

    C12-Obh - - - 3.5 ± 0.2

    Angles (degrees)

    N-Hn-Ob 110 ± 19 120 ± 11 151 ± 20 150 ± 7

    N-Hn-Obh 162 ± 15 164 ± 18 121 ± 11 126 ± 14

    C11-Hc-Obh 140 ± 29 137 ± 13 125 ± 14 129 ± 17

    C11-Hc-Ob 134 ± 13 124 ± 15 134 ± 22 153 ± 29

    C12-Hc-Ob - - - 125 ± 15

    C12-Hc-Obh - - - 130 ± 6

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