Template for Electronic Submission to ACS Journals · S19 18. Selectivity of compounds 5 and 6...
24
S1 Supplementary Information Ratiometric/‘turn-On’ fluorescent chemosensor for CN - : mimicking XNOR logic function with Fe 3+ ions Manoj Kumar,* Rajesh Kumar, Vandana Bhalla Department of Chemistry, UGC Sponsored-Center for Advance Studies-1, Guru Nanak Dev University Amritsar (Pb)-143005, India Email:[email protected] Contents Page No. 1. 1 H NMR spectrum of 5 in CDCl 3 . S2 2. FAB mass spectrum of 5. S3 3. 1 H NMR spectrum of 6 in CDCl 3 . S4 4. 13 C NMR spectrum of 6 in CDCl 3 . S5 5. ESI-MS mass spectrum of 6. S6 6. 1 H NMR spectrum of 7 in CDCl 3 . S7 7. 13 C NMR spectrum of 7 in CDCl 3 . S8 8. FAB-MS mass spectrum of 7. S9 9. Fluorescence spectra of compound 7 with CN - in THF. S10 10. Selectivity of compound 7 towards CN - in the presence of different anions in THF. S11 11. 1 H NMR of compound 5 + CN - ions in CDCl 3 . S12 12. 1 H NMR of compound 6 + CN - ions in CDCl 3 . S13 13. Selectivity of compound 5 towards CN - in the presence of different anions in THF. S14 14. Job plot of compounds 5-7 with CN - in THF. S15 15. Fluorescence spectra of compound 5 with Fe 3+ in THF. S16 16. Fluorescence emission spectra of receptor 7 upon various addition of Fe 3+ in THF. S17 17. Pictorial representation of binding modes of compound 5-7 with Fe 3+ ion. S18 18. Selectivity of compounds 5 and 6 towards Fe 3+ in THF. S19 19. Selectivity and competitive selectivity of 7 towards Fe 3+ in THF. S20 20. Job plot of compounds 5-7 with Fe 3+ in THF. S21 21. Fluorescence spectra of 6.Fe 3+ and 7.Fe 3+ complexes upon addition of CN - in THF. S22 22. Reversibility of 5.Fe 3+ complex with addition of CN - ion. S23 23. Selectivity of 5.Fe 3+ complex towards CN - in the presence of other anions in THF. S24 Electronic Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2013
Transcript of Template for Electronic Submission to ACS Journals · S19 18. Selectivity of compounds 5 and 6...
S1
Supplementary Information
Ratiometric/‘turn-On’ fluorescent chemosensor for CN-:
mimicking XNOR logic function with Fe3+
ions Manoj Kumar,*
Rajesh Kumar,
Vandana Bhalla
Department of Chemistry, UGC Sponsored-Center for Advance Studies-1,
Guru Nanak Dev University
Amritsar (Pb)-143005, India
Email:[email protected]
Contents Page No.
1. 1H NMR spectrum of 5 in CDCl3.
S2
2. FAB mass spectrum of 5. S3
3. 1H NMR spectrum of 6 in CDCl3. S4
4. 13C NMR spectrum of 6 in CDCl3. S5
5. ESI-MS mass spectrum of 6. S6
6. 1H NMR spectrum of 7 in CDCl3. S7
7. 13C NMR spectrum of 7 in CDCl3. S8
8. FAB-MS mass spectrum of 7. S9
9. Fluorescence spectra of compound 7 with CN- in THF. S10
10. Selectivity of compound 7 towards CN- in the presence of different anions in THF. S11
11. 1H NMR of compound 5 + CN- ions in CDCl3. S12
12. 1H NMR of compound 6 + CN- ions in CDCl3. S13
13. Selectivity of compound 5 towards CN- in the presence of different anions in THF. S14
14. Job plot of compounds 5-7 with CN- in THF. S15
15. Fluorescence spectra of compound 5 with Fe3+
in THF. S16
16. Fluorescence emission spectra of receptor 7 upon various addition of Fe3+
in THF. S17
17. Pictorial representation of binding modes of compound 5-7 with Fe3+
ion. S18
18. Selectivity of compounds 5 and 6 towards Fe3+
in THF. S19
19. Selectivity and competitive selectivity of 7 towards Fe3+
in THF. S20
20. Job plot of compounds 5-7 with Fe3+
in THF. S21
21. Fluorescence spectra of 6.Fe3+
and 7.Fe3+
complexes upon addition of CN- in THF. S22
22. Reversibility of 5.Fe3+
complex with addition of CN- ion. S23
23. Selectivity of 5.Fe3+
complex towards CN- in the presence of other anions in THF. S24
Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2013
S2
1. 1H NMR spectrum of 5 in CDCl3.
Figure S1. 1H NMR spectrum of 5 in CDCl3.
S
OHOH OOSS S
NH HN
O O
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S3
2. FAB mass spectrum of 5.
Figure S2. FAB mass spectrum of 5.
S
OHOH OOSS S
NH HN
O O
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S4
3. 1H NMR spectrum of 6 in CDCl3.
Figure S3. 1H NMR spectrum of 6 in CDCl3.
S
O
OOS SS
HNNH
O
O
O
O
OO
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S5
4. 13C NMR Spectrum of 6 in CDCl3.
Figure S4. 13
C NMR spectrum of 6 in CDCl3.
S
O
OOS SS
HNNH
O
O
O
O
OO
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S6
5. ESI mass spectrum of 6.
Figure S5. ESI-MS mass spectrum of 6.
S
O
OOS SS
HNNH
O
O
O
O
OO
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S7
6. 1H NMR spectrum of 7 in CDCl3.
Figure S6. 1H NMR spectrum of 7 in CDCl3.
S
OO
OOS SS
HNNHOO
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S8
7. 13C NMR Spectrum of 7 in CDCl3.
Figure S7. 13
C NMR spectrum of 7 in CDCl3.
S
OO
OOS SS
HNNHOO
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S9
8. FAB-MS mass spectrum of 7.
Figure S8. ESI-MS mass spectrum of 7.
S
OO
OOS SS
HNNHOO
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S10
9. Fluorescence spectra of compound 7 with CN- in THF.
Figure S9 Fluorescence emission spectra of receptor 7 (10 µM) upon various addition of CN
- (0-500 equiv) in THF.
Inte
ns
ity
Wavelength (nm)
0
500 equiv
CN-
Inte
ns
ity
Wavelength (nm)
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S11
10. Selectivity of compound 7 towards CN- in the presence of different anions in THF.
I 454/I
350
(A)
(B)
A B C D E F G H I J Anions
Figure S10. (A) Ratiometric selectivity of 7 (10 µM) towards CN-
upon addition of different anions and (B) Ratiometric competitive selectivity of 7 (10 µM) towards CN
- in the presence of different
anions in THF. A=FL, B=F-, C=Cl
-, D=Br
-, E=I
-, F=OAc
-, G=CN
-,
H=HSO4, I= NO3-, J=H2PO4
-.
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S12
11. 1H NMR of compound 5 + CN
- ions in CDCl3.
Figure S11. 1H NMR of compound 5 + CN
- ions in CDCl3.
NH OH
NCH2
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S13
12. 1H NMR of compound 6 + CN
- ions in CDCl3.
Figure S12. 1H NMR of compound 6 + CN
- ions in CDCl3.
NH
NCH2
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S14
13. Selectivity of compound 5 towards CN- in the presence of different anions in THF.
(A)
(B)
A B C D E F G H I Anions
(Io-I
)/I o
X1
00
Figure S13. (A) Selectivity of 5 (10 µM) towards CN-
upon addition of different anions and (B) Competitive
selectivity of 5 (10 µM) towards CN- in the presence of
different anions in THF. A=F-, B=Cl
-, C=Br
-, D=I
-,
E=OAc-, F=CN
-, G=HSO4
-, H= NO3
-, I=H2PO4
-.
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S15
14. Job plot of compounds 5-7 with CN- in THF.
Figure S14. Job’s plot of 5-7 with CN- in THF.
I o-I
5
6
7
Mole fraction of CN-
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S16
15. Fluorescence spectra of compound 6 with Fe3+
in THF.
Figure S15 Fluorescence emission spectra of receptor 6 (10 µM) upon various addition of Fe
3+ (0-100 equiv) in THF.
Inte
ns
ity
Wavelength (nm)
0
100 equiv
Fe3+
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S17
16. Fluorescence emission spectra of receptor 7 upon various addition of Fe3+
in THF.
Figure S16. Fluorescence emission spectra of receptor 7 (10 µM)
upon various addition of Fe3+
(0-100 equiv) in THF.
Inte
ns
ity
Wavelength (nm)
0
100 eq
Fe3+
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S18
17. Pictorial representation of binding modes of compound 5-7 upon addition of Fe3+
ion.
Figure S17. Pictorial representation of binding modes of compound 5-7 upon
addition of Fe3+
ion.
S S
S S
S
OO
ORORS SSS
O
ORORS SS
O
OO
O
S
OHOH ROORSS S
Fe3+
O
HN
O
NH
S S
S S
O O
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S19
18. Selectivity of compounds 5 and 6 towards Fe3+
in THF.
Figure S18. (A) Selectivity of 5 (10 µM) towards Fe3+
upon
addition of different cations and (B) Competitive selectivity
of 5 (10 µM) towards Fe3+
in the presence of different
cations in 10% aqueous ethanol. A=Li+, B=Na
+, C=K
+,
D=Ba2+
, E=Mg2+
, F=Ni2+
, G=Cu2+
, H= Zn2+
, I=Ag+, J=
Cd2+
, K=Hg2+
, L=Pb2+
, M=Co2+
, N=Fe2+
, O=Fe3+
.
(A)
(B)
A B C D E F G H I J K L M N O Cations
(Io-I
)/I o
X1
00
Figure S19. Selectivity of 6 (10 µM) towards Fe3+
and K+ upon
addition of different cations in THF. A=Li+, B=Na
+, C=K
+,
D=Ba2+
, E=Mg2+
, F=Ni2+
, G=Cu2+
, H= Zn2+
, I=Ag+, J= Cd
2+,
K=Hg2+
, L=Pb2+
, M=Co2+
, N=Fe2+
, O=Fe3+
.
I o-I
A B C D E F G H I J K L M N
O
Cations
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S20
19. Selectivity and competitive selectivity of 7 towards Fe3+
in THF.
20. Job plot of compounds 5-7 with Fe3+
in THF.
A B C D E F G H I J K L M N O Cations
Figure S20. (A) Selectivity of 7 (10 µM) towards
Fe3+
upon addition of different cations and (B)
Competitive selectivity of 7 (10 µM) towards Fe3+
in
the presence of different cations in 10% aqueous
ethanol. A=Li+, B=Na
+, C=K
+, D=Ba
2+, E=Mg
2+,
F=Ni2+
, G=Cu2+
, H= Zn2+
, I=Ag+, J= Cd
2+, K=Hg
2+,
L=Pb2+
, M=Co2+
, N=Fe2+
, O=Fe3+
.
(A)
(B)
(Io-I
)/I o
X1
00
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S21
21. Fluorescence emission spectra of 6.Fe3+
and 7.Fe3+
complexes upon addition of CN- in THF.
I o-I
Mole fraction of guest
5
6
7
Figure S21. Job’s plot of 5-7 with Fe3+
in THF.
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S22
22. Reversibility of 5.Fe3+
complex with addition of CN- ion.
Inte
ns
ity
7
Wavelength (nm)
400 eq
0
CN-
7.Fe3+
Figure S23. Fluorescence emission spectra of receptor 7.Fe3+
complex upon various addition of CN- (0-400 equiv) in THF.
Inte
ns
ity
6
Wavelength (nm)
400 equiv
0
CN-
6+Fe3+
Figure S22 Fluorescence emission spectra of receptor 6.Fe3+
complex upon various addition of CN
- (0-400 equiv) in THF.
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S23
23. Selectivity of 5.Fe3+
complex towards CN- in the presence of other anions in THF.
Figure S24. Reversibility of 5.Fe3+
complex with addition of CN- ion.
Fe3+
(Off state)
FL
CN- (On state)
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S24
I-I o
Anions
Figure S25. Selectivity of 5.Fe3+
complex towards CN- upon
addition of different anions in THF. A=F-, B=Cl
-, C=Br
-, D=I
-,
E=OAc-, F=CN
-, G=HSO4
-, H= NO3
-, I=H2PO4
-. Io indicates
fluorescence intensity of 5.Fe3+
complex and I indicate
fluorescence intensity of 5.Fe3+
-anion complex.
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