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Electronic Supplementary Information
Enhanced mechanofluorochromic properties of 14-dihydropyridine-based fluorescence molecules caused by the introduction of halogen atoms
Yating Chen Yibin Zhou Zhiqiang Wang Mengzhu Wang Wenxia Gao Yunbing Zhou Miaochang Liu Xiaobo Huang and Huayue Wu
College of Chemistry and Materials Engineering Wenzhou University Wenzhou 325035 P R China
E-mail xiaobhuangwzueducn (X Huang) huayuewuwzueducn
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is copy The Royal Society of Chemistry 2019
2
Contents
Fig S1 Crystal CMD-Cl (a) Molecular packing mode (b) The CndashHO bond and CndashHπ bond in the same column (c) The CndashHO bond and CndashHN bond between different columns
Fig S2 Crystal CMD-Br (a) Molecular packing mode (b) The CndashHO bond and CndashHπ bond in the same column (c) The CndashHO bond between different columns
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000005010015020025030035 (c)
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)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S3 CMD-F Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
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)
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fw
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1200 (d) Glycerol vol fractions
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Fig S4 CMD-Cl Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
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0200
400600800
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12001400 (b)
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nsity
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)
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05 (c)
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fw
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nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S5 CMD-Br Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 50 60 and 70
6
5 10 15 20 25 30 35 40 45 50
Inte
nsity
(a u
) Simulated Original
(a)
2deg5 10 15 20 25 30 35 40 45 50
(b) Simulated Original
2deg
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(a u
)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(c)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(d)
Fig S6 Comparison of XRD curves of the original samples of the CMD derivatives and the simulated XRD curves obtained from the corresponding single crystals CMD-H (a) CMD-F (b) CMD-Cl (c) and CMD-Br (d)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
2
Contents
Fig S1 Crystal CMD-Cl (a) Molecular packing mode (b) The CndashHO bond and CndashHπ bond in the same column (c) The CndashHO bond and CndashHN bond between different columns
Fig S2 Crystal CMD-Br (a) Molecular packing mode (b) The CndashHO bond and CndashHπ bond in the same column (c) The CndashHO bond between different columns
3
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)
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000005010015020025030035 (c)
Abs
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nce (
a u
)
Wavelength (nm)
0 10 20 30 40 50 60 70 80 90 99
fw
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200
400600800
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12001400 (d)
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S3 CMD-F Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
4
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nsity
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)
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300 350 400 450 500 550 600 65000
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Abs
orba
nce (
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)
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fw
500 550 600 650 7000
300
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1200 (d) Glycerol vol fractions
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Fig S4 CMD-Cl Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
5
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0200
400600800
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12001400 (b)
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nsity
(a u
)
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00
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1200 (d)
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S5 CMD-Br Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 50 60 and 70
6
5 10 15 20 25 30 35 40 45 50
Inte
nsity
(a u
) Simulated Original
(a)
2deg5 10 15 20 25 30 35 40 45 50
(b) Simulated Original
2deg
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(a u
)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(c)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(d)
Fig S6 Comparison of XRD curves of the original samples of the CMD derivatives and the simulated XRD curves obtained from the corresponding single crystals CMD-H (a) CMD-F (b) CMD-Cl (c) and CMD-Br (d)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
3
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nsity
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)
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(b)
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000005010015020025030035 (c)
Abs
orba
nce (
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)
Wavelength (nm)
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fw
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200
400600800
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12001400 (d)
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S3 CMD-F Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
4
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nsity
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)
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300 350 400 450 500 550 600 65000
01
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03
04
05 (c)
Abs
orba
nce (
a u
)
Wavelength (nm)
0 10 20 30 40 50 60 70 80 90 99
fw
500 550 600 650 7000
300
600
900
1200 (d) Glycerol vol fractions
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Fig S4 CMD-Cl Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
5
0 20 40 60 80 100
0200
400600800
1000
12001400 (b)
Inte
nsity
(a u
)
Water fraction(volume )
300 350 400 450 500 550 600 650
00
01
02
03
04
05 (c)
Abs
orba
nce (
a u
)
Wavelength (nm)
0 10 20 30 40 50 60 70 80 90 99
fw
500 550 600 650 7000
200
400
600
800
1000
1200 (d)
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S5 CMD-Br Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 50 60 and 70
6
5 10 15 20 25 30 35 40 45 50
Inte
nsity
(a u
) Simulated Original
(a)
2deg5 10 15 20 25 30 35 40 45 50
(b) Simulated Original
2deg
Inte
nsity
(a u
)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(c)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(d)
Fig S6 Comparison of XRD curves of the original samples of the CMD derivatives and the simulated XRD curves obtained from the corresponding single crystals CMD-H (a) CMD-F (b) CMD-Cl (c) and CMD-Br (d)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
4
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)
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fw
500 550 600 650 7000
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1200 (d) Glycerol vol fractions
Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Fig S4 CMD-Cl Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 70 and 99
5
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0200
400600800
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12001400 (b)
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nsity
(a u
)
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300 350 400 450 500 550 600 650
00
01
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fw
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Inte
nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S5 CMD-Br Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 50 60 and 70
6
5 10 15 20 25 30 35 40 45 50
Inte
nsity
(a u
) Simulated Original
(a)
2deg5 10 15 20 25 30 35 40 45 50
(b) Simulated Original
2deg
Inte
nsity
(a u
)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(c)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(d)
Fig S6 Comparison of XRD curves of the original samples of the CMD derivatives and the simulated XRD curves obtained from the corresponding single crystals CMD-H (a) CMD-F (b) CMD-Cl (c) and CMD-Br (d)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
5
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0200
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)
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00
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)
Wavelength (nm)
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fw
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nsity
(a u
)
Wavelength (nm)
0 20 40 60 80 90
Glycerol vol fractions
Fig S5 CMD-Br Fluorescence spectra (a) changes in the fluorescence intensity (b) and UV-vis absorption spectra (c) in DMSO-water mixtures (100 μmolL) with fw values from 0 to 99 Fluorescence spectra (d) in DMSO-glycerol mixtures (100 μmolL) with the glycerol volume fraction from 0 to 90 The insets in (a) show digital photographs of the fluorescence of mixtures with fw = 0 50 60 and 70
6
5 10 15 20 25 30 35 40 45 50
Inte
nsity
(a u
) Simulated Original
(a)
2deg5 10 15 20 25 30 35 40 45 50
(b) Simulated Original
2deg
Inte
nsity
(a u
)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(c)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(d)
Fig S6 Comparison of XRD curves of the original samples of the CMD derivatives and the simulated XRD curves obtained from the corresponding single crystals CMD-H (a) CMD-F (b) CMD-Cl (c) and CMD-Br (d)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
6
5 10 15 20 25 30 35 40 45 50
Inte
nsity
(a u
) Simulated Original
(a)
2deg5 10 15 20 25 30 35 40 45 50
(b) Simulated Original
2deg
Inte
nsity
(a u
)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(c)
5 10 15 20 25 30 35 40 45 50 2deg
Inte
nsity
(a u
)
Simulated Original
(d)
Fig S6 Comparison of XRD curves of the original samples of the CMD derivatives and the simulated XRD curves obtained from the corresponding single crystals CMD-H (a) CMD-F (b) CMD-Cl (c) and CMD-Br (d)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
7
Fig S7 1H NMR of compound 2 (DMSO-d6 500 MHz)
Fig S8 13C NMR of compound 2 (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
8
Fig S9 1H NMR of compound 3a (DMSO-d6 500 MHz)
Fig S10 13C NMR of compound 3a (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
9
Fig S11 1H NMR of compound 3b (DMSO-d6 500 MHz)
Fig S12 13C NMR of compound 3b (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
10
Fig S13 1H NMR of compound 3c (DMSO-d6 500 MHz)
Fig S14 13C NMR of compound 3c (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
11
Fig S15 1H NMR of compound 3d (DMSO-d6 500 MHz)
Fig S16 13C NMR of compound 3d (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
12
Fig S17 1H NMR of CMD-H (DMSO-d6 500 MHz)
Fig S18 13C NMR of CMD-H (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
13
Fig S19 1H NMR of CMD-F (DMSO-d6 400 MHz)
Fig S20 13C NMR of CMD-F (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
14
Fig S21 1H NMR of CMD-Cl (DMSO-d6 500 MHz)
Fig S22 13C NMR of CMD-Cl (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
15
Fig S23 1H NMR of CMD-Br (DMSO-d6 500 MHz)
Fig S24 13C NMR of CMD-Br (DMSO-d6 125 MHz)
![Fluorescence near metal tips: The roles of energy transfer ... › elec603 › spring2008 › Meeting_Blog › Ent… · fluorescence spectra [14, 21], tip-molecule distance dependence](https://img.pdfslide.us/doc/110x75/5f26a57ec04bc541de471408/fluorescence-near-metal-tips-the-roles-of-energy-transfer-a-elec603-a-spring2008.jpg)
