dqgwkh ...fluorescence sensing and intracellular imaging of pd2+ ion by a novel coumarinyl-rhodamine...
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![Page 1: DQGWKH ...Fluorescence sensing and intracellular imaging of Pd2+ ion by a novel coumarinyl-rhodamine Schiff base† Arup Kumar Adak, Saikat Manna, Bankim Chandra Ghosh, Sudipta Pathak,](https://reader033.vdocuments.us/reader033/viewer/2022050522/5fa6220dc8c3a521d9741fe4/html5/thumbnails/1.jpg)
Fluorescence sensing and intracellular imaging of Pd2+ ion by a novel
coumarinyl-rhodamine Schiff base†
Arup Kumar Adak, Saikat Manna, Bankim Chandra Ghosh, Sudipta Pathak, Rakesh Purkait and
Chittaranjan Sinha
O NN
N
ONH2
CHOOHO
Me
O
O NN
N
ON
OHO
Me
O
Ethanol, Reflux
HCR
A
B
CHOOHO
Me
O
O NN
N
ONH2
OHO
Me
OOHHO
O NN
COOH
Cl
A
B
i ii
iii
Scheme S1: Structure and synthesis of sensor HCR where (i). Ethyl acetoacetate, Conc. H2SO4;
(ii). Hexamine, Acetic acid; (iii). Excess Ethelene diamine, EtOH, Reflux.
Electronic Supplementary Material (ESI) for New Journal of Chemistry.This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019
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Figure S1. FTIR spectrum of HCR.
Absorption, cm-1 Assignments
~3400
2970.18
~2800
1727.39
1668.08
1614.36
~1600
1512.24
1218.35
O – H stretching (broad and very weak)
C-H stretching (Ar-H)
C – H stretching (-CH3 and –CH2-)
C=O stretching (α,β-unsaturated δ-lactone.
C=O stretching (α, β-unsaturated-5-membered amide or -lactam).
C = N stretching (Schiff’s base)
C = C stretching (aromatic ring)
C – N stretching.
C – O – C stretching (aromatic ether)
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Figure S2. Mass spectrum of HCR.
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Figure S3. 1H NMR spectrum of HCR in CDCl3 solution.
Figure S4. 13C NMR spectrum of HCR in CDCl3 solution.
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Fig. S5 The linear dynamic response of HCR for Pd2+ and the determination of the limit of detection (LOD) of Pd2+.
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Figure S6: Job’s plot of HCR and Pd2+ reaction and associated absorbance change
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Y = A + B*X
Y= (0.596 10-5± 0.060) + (1.099 ± 0.185) *
Figure S7. Benesi-Hildebrand plot obtained from the fluorescence titration data
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Figure S8. FTIR spectrum of [CR--Pd2+]+ complex in KBr pellete
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Figure S9. ESI-MS spectrum of [CR--Pd2+]+
Figure S10. Cellular image after treatment with HCR (5 M)
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Table S1 Frontier molecular orbitals contributions of HCR
MO Energy (eV) Rodamine CoumarineLUMO+10 0.76 96 4LUMO+9 0.51 38 62LUMO+8 0.46 83 17LUMO+7 0.25 2 98LUMO+6 0.06 100 0LUMO+5 -0.18 100 0LUMO+4 -0.24 99 1LUMO+3 -0.36 8 92LUMO+2 -0.81 95 5LUMO+1 -1.0 20 80LUMO -2.03 1 99HOMO -4.94 100 0HOMO-1 -5.21 100 0HOMO-2 -5.76 100 0HOMO-3 -6.17 95 5HOMO-4 -6.41 86 14HOMO-5 -6.44 96 4HOMO-6 -6.5 2 98HOMO-7 -6.77 97 3HOMO-8 -6.89 91 9HOMO-9 -6.92 65 65HOMO-10 -7.04 97 3
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Table S2 Frontier molecular orbitals contributions of [CR--Pd2+]+
MO Energy (eV) Pd Rodamine CoumarineLUMO+10 -1.66 34 62 4LUMO+9 -1.82 3 3 95LUMO+8 -2.7 0 100 0LUMO+7 -2.79 0 100 0LUMO+6 -3.02 0 100 0LUMO+5 -3.25 0 100 0LUMO+4 -3.36 1 4 95LUMO+3 -3.82 2 91 6LUMO+2 -3.93 3 25 72LUMO+1 -4.32 55 34 10LUMO -5.26 0 100 0HOMO -7.58 7 7 86HOMO-1 -8.07 0 100 0HOMO-2 -8.46 21 56 23HOMO-3 -8.61 20 24 57HOMO-4 -8.81 27 65 7HOMO-5 -8.89 50 46 4HOMO-6 -9.08 31 39 30HOMO-7 -9.22 2 7 92HOMO-8 -9.33 9 33 59HOMO-9 -9.5 4 73 23HOMO-10 -9.71 15 61 24