SUPPORTING INFORMATION
Chloro(triphenylphosphole)gold(I) - A selective Chemosensor for Cysteine
MARUTHAI KUMARAVEL and MARAVANJI S BALAKRISHNA*
a
Phosphorus Laboratory, Department of Chemistry, Indian Institute of Technology Bombay,
Powai, Mumbai 400076, India
e-mail: krishna@chem.iitb.ac.in; msb_krishna@iitb.ac.in
Contents
Figure S1. 31P{1H} NMR (CDCl3, 162 MHz) of [AuL].
Figure S2. The emission spectra of compound [AuL] in methanol at (a) different excited
wavelengths. (b) at normalized intensity.
Chart S1. Chemical Structure of natural amino acids and biologically important thiols.
Figure S3. Fluorescence spectra obtained for the titration of [AuL] with different amino acids in
methanol, λex = 390 nm. [AuL] = 2 µM.
Figure S4. Stern-volmer plots of fluorescence quenching of [AuL] with a) Cys with error bars,b)
without error bars, c) DTT and d) Hcy.
Table S1. Decomposition temperature at 10% weight loss (Td10) of similar phosphole
derivatives.
Figure S5. TGA profile of [AuL] under a stream of N2 at a heating rate of 10 °C min-1.
Table S2. Comparison of methods for the determination of Cys
References
1
30.34
250
200
150
100
50
0
-50
ppm
Figure S1. 31P{1H} NMR (CDCl3, 162 MHz) of [AuL]
Figure S2. The emission spectra of compound [AuL] in methanol at (a) different excited
wavelengths. (b) at normalized intensity.
2
Chart S1. Chemical Structure of natural amino acids and biologically important thiols.
3
0.0
400
1
2
3 4 5 6
[Ala]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
200
3 4 5 6
[Glu]/[AuL]
7
Gly
0.9
0.3
0.0
400
1 2 3 4 5 6 7
[Gly]/[AuL]
200
Wavelength (nm)
1000
Intensity (a.u.)
I/Io
0.6
0.3
600
0.0
1
2
3 4 5 6
[Leu]/[AuL]
7
400
200
0
400 450 500 550 600 650
Wavelength (nm)
1000
800
1.2
0.9
600
0.6
0.3
0.0
400
1
2
3 4 5 6
[Met]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
1000
0.6
0.3
0.0
1
2
3 4 5 6
[Pro]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
800
Ser
0.9
0.3
0.0
400
I/Io
2
3 4 5 6
[Ala]/[AuL]
7
800
1.2
Ile
0.9
0.6
0.3
600
0.0
1
2
3 4 5 6
[Ile]/[AuL]
7
400
200
800
Phe
1.2
0.9
0.6
600
0.3
0.0
1
400
2
3 4 5 6
[Phe]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
1000
0.6
600
1
200
1.2
I/I o
0.9
Intensity (a.u.)
1.2
I/I o
Pro
0.0
400
1000
Met
I/Io
Leu
0.3
0
400 450 500 550 600 650
Wavelength (nm)
0
400 450 500 550 600 650
0.9
0.9
1000
600
1.2
1.2
0.6
600
1.2
Intensity (a.u.)
2
Gln
0
400 450 500 550 600 650
Wavelength (nm)
Intensity (a.u.)
1
1000
Intensity (a.u.)
7
0.6
0
400 450 500 550 600 650
Wavelength (nm)
Intensity (a.u.)
3 4 5 6
[Asn]/[AuL]
1
2
3 4 5 6
[Ser]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
Intensity (a.u.)
0.3
200
400
2
I/I o
0.6
400
600
1
400
800
Intensity (a.u.)
0.9
I/Io
Intensity (a.u.)
Glu
0.0
800
0.0
1000
1.2
600
800
600
0
400 450 500 550 600 650
Wavelength (nm)
1000
800
0.3
800
I/Io
0.3
0.6
I/Io
600
0.9
800
600
400
Val
1.2
0.9
I/Io
0.6
800
1.2
Intensity (a.u.)
0.9
1000
Asn
I/Io
1000
1.2
Intensity (a.u.)
800
Ala
I/Io
Intensity (a.u.)
1000
0.6
0.3
0.0
1
2
3 4 5 6
[Val]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
Figure S3. Fluorescence spectra obtained for the titration of [AuL] with different amino acids in
methanol, λex = 390 nm. [AuL] = 2 µM.
4
600
0.3
0.0
400
1
2
3 4 5 6
[Trp]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
600
0.3
0.0
400
1
2
3 4 5 6
[Thr]/[AuL]
7
200
0.6
600
0.3
0.0
400
1
2 3 4 5
[Asp]/[AuL]
6
7
200
800
600
400
1.2
I/Io
0.9
600
0.6
0.3
0.0
400
1
2
3 4 5 6
[Arg]/[AuL]
7
200
Wavelength (nm)
His
1.2
0.9
0.6
0.3
0.0
1
2
3 4 5 6
[His]/[AuL]
7
200
Intensity (a.u.)
0.9
Arg
1000
I/Io
1.2
Intensity (a.u.)
Asp
800
0
400 450 500 550 600 650
1000
I/I o
Intensity (a.u.)
0.6
0
400 450 500 550 600 650
Wavelength (nm)
1000
800
0.9
800
Lys
1.2
0.9
0.6
600
400
I/I o
0.6
800
1000
1.2
Thr
I/I o
0.9
Intensity (a.u.)
1.2
Intensity (a.u.)
800
1000
Trp
I/I o
Intensity (a.u.)
1000
0.3
0.0
1 2 3 4 5 6 7
[Lys]/[AuL]
200
0
400 450 500 550 600 650
0
400 450 500 550 600 650
0
400 450 500 550 600 650
Wavelength (nm)
Wavelength (nm)
Wavelength (nm)
800
Tyr
1.2
0.9
0.6
600
I/Io
Intensity (a.u.)
1000
0.3
0.0
400
1
2
3 4 5 6
[Tyr]/[AuL]
7
200
0
400 450 500 550 600 650
Wavelength (nm)
Figure S3. Contd. Fluorescence spectra obtained for the titration of [AuL] with different amino
acids in methanol, λex = 390 nm. [AuL] = 2 µM.
5
Figure S4. Stern-volmer plots of fluorescence quenching of [AuL] with a) Cys, b) DTT and c)
Hcy.
6
Figure S5. TGA profile of [AuL] under a stream of N2 at a heating rate of 10°C min-1.
7
Table S1. Decomposition temperature at 10% weight loss (Td10) of similar phosphole
derivativesa
Td10 (˚C)
Ref.
Entry
Td10(˚C)
Ref.
1
210
S1
9
226
S3
2
214b
S2
10
269
S3
3
253
S1
11
268
S3
4
165 b
S2
12
287
S1
5
145b
S2
13
252
S1
6
213
S1
14
251
S1
7
220
S1
15
218
S1
8
220
S1
16
268
This
work
Entry
a
compound
compound
determined by thermogravimetric analysis under an atmosphere of nitrogen. bdecomposition
temperature measured at 5% weight loss.
8
Table S2. Comparison of methods for the determination of Cys
Method
Fluorimetry
Spectrophotometry
Spectrophotometry
Spectrophotometry
Spectrophotometry
Voltammetry
Fluorimetry
Fluorimetry
Electrochemical
determination
Fluorimetry
Fluorimetry
Fluorimetry
Reagent
Mercaptoacetic acidcapped CdSe/ZnS
QDs
Ag NPs in the
presence of Ca2+
Triangular silver
nanoprisms
Triiodide ion and
hexadecylpyridinium
chloride
Ferric ions and
ferrozine
Carbon-paste
electrode
Thiazole orange
/DNA/Hg2+
Cu2+ morin complex
Polymers/gold
nanoparticles hybrid
nanocomposites
Fluorescein and Au
nanoparticles
Triazole-Based
Calix[4]arene
Conjugates.
Chloro(triphenyl
phosphole) gold(I)
Analytical
ranges
(µM)
Detection
limit
(nM)
Determination
index
wavelength
(nm)
Reference
0.01
3.8
565
S4
0.25–10
85
524/396
S5
Not given
160
509
S6
0.00820.12
4.9
500
S7
0.17-50
Not given
562
S8
0.5-100
200
-
S9
0.00290.11
0.65-22
5.1
540
S10
65.2
539
S11
0.5-200
50
-
S12
0.0250.325
7.27
517
S13
2-20
58
380
S14
1-20
500
390
This work
9
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