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D1ay00963j1.Pdf Electronic Supplementary Material (ESI) for Analytical Methods. This journal is © The Royal Society of Chemistry 2021 A bio-compatible pyridine-pyrazole hydrazide based compartmental receptor for Al3+ sensing and its application in cell imaging Bhriguram Das,a,b Malay Dolai,c Avijit Ghosh,d Anamika Dhara,e Ananya Das Mahapatra,f Debprasad Chattopadhyay,f,g Subhabrata Mabhai,h Atanu Jana,*i Satyajit Dey,*b and Ajay Misra*a aDepartment of Chemistry, Vidyasagar University, Midnapore-721102, West Bengal, India. E-mail: [email protected] ; [email protected] . Fax: +91 3222 275329 bDepartment of Chemistry, Tamralipta Mahavidyalaya, Purba Medinipur 721636, India. Email: [email protected] cDepartment of Chemistry, Prabhat Kumar College, Contai, Purba Medinipur 721404, West Bengal, India. dCenter for Research in Nanoscience and Nanotechnology, Technology Campus, University of Calcutta, Salt Lake, Kolkata 700106, India eDepartment of Chemistry, Hiralal Mazumdar Memorial College For Women, Dakshineswar, North 24 Parganas, Kolkata 700035, India fICMR-Virus Unit, ID & BG Hospital Campus, 57 Dr Suresh C Banerjee Road, Beliaghata, Kolkata 700010, India gICMR-National Institute of Traditional Medicine, Nehru Nagar, Belagavi 59001 Karnataka, India hDepartment of Chemistry, Mahishadal Raj College, Purba Medinipur, 721628, India iDivision of Physics and Semiconductor Science, Dongguk University, Seoul, 04620, South Korea. Email: [email protected] S1 Fig. 12.5 S1 : 0.98 8.6 11.997 8.634 I 11.5 H 8.516 NMR 8.505 1.00 11.094 f1 10.5 9.162 8.3 (ppm) of 8.634 the 8.060 8.516 8.505 8.040 ligand 9.5 8.025 8.060 8.0 8.021 8.040 7.985 8.025 H 1.00 7.966 8.021 8.5 2 PPC 1.02 7.964 7.985 1.01 7.966 2.11 7.964 (Bruker 7.5 1.05 7.449 7.449 7.446 7.446 7.434 7.434 7.3 500 4.23 7.430 6.5 7.430 f1 7.419 7.419 (ppm) MHz, 7.415 7.415 f1 6.883 7.0 (ppm) 6.883 5.5 6.864 6.864 DMSO-d 6.817 6.817 6.814 6.814 6.7 4.5 6.795 6.795 6.782 6.782 6 6.713 6.713 ) 6.694 6.694 3.5 6.675 6.675 6.672 2.5 3.15 2.591 1.5 0.5 S 2 13 Fig. S2 : C NMR of the ligand H2PPC (Bruker 125 MHz, DMSO-d6) S3 Fig. S3 Mass spectra of ligand H2PPC. 337.1175 (calculated), 338.1247 (observed) correspond to + + (H2PPC +H ), and 360.1155 correspond to (H2PPC +Na ) S4 Fig. S4 FTIR spectra of the probe H2PPC (KBr pallet). S5 BIP/BIP/MBAMBBD26R BIP_BIP_MBAMBBD26R 12.008 8.636 8.516 8.505 8.488 8.063 8.059 8.043 8.025 8.021 7.985 7.965 7.450 7.435 7.419 6.888 6.869 6.858 6.838 6.820 6.817 6.800 6.782 6.753 6.716 6.697 6.678 2.591 8.636 8.516 8.505 8.488 8.063 8.059 8.043 8.025 8.021 7.985 7.965 7.450 7.435 7.419 6.888 6.869 6.858 6.838 6.820 6.817 6.800 6.782 6.716 6.697 6.678 8.6 8.4 8.2 8.0 7.5 7.3 7.1 6.9 6.7 f1 (ppm) f1 (ppm) 1.01 1.00 1.06 1.12 1.07 1.15 4.87 3.83 14.0 12.5 11.0 9.5 8.5 7.5 6.5 5.5 4.5 3.5 2.5 1.5 0.5 f1 (ppm) I 3+ Fig. S5 : H NMR of the ligand H2PPC -Al complex (500 MHz, DMSO-d6) S6 13 3+ Fig. S6 : C NMR of the ligand H2PPC-Al complex (Bruker 125 MHz, DMSO-d6) S7 3+ Fig. S7 Mass spectra of the H2PPC + Al complex (2:1). Calculated 699.2009, observed 699.1948 3+ + correspond to [2H2PPC+ Al - 2H ] S8 3+ Fig. S8 FT-IR spectra of the H2PPC-Al complex (KBr pallet) S9 100 0.6 ) H PPC 2 . Cu (HPPC) (NO ) u 2 2 3 2 . 80 430 nm a 404 nm ( e H2PPC y c 0.4 t n i 60 Cu2(HPPC)2(NO3)2 a 335 nm s b n r e o 0.2 t 40 s n I b 415 nm . l A F 20 0.0 0 300 400 500 600 400 500 600 Wavelengtm (nm) Wavelengtm (nm) 2+ Fig. S9 : (a) absorption spectra and (b) emission spectra (λex = 340 nm ) of H2PPC and H2PPC-Cu complex in MeOH-H2O (9:1,v/v) Fig. S10 photographic image of H2PPC + different metal ions under ambient light in MeOH-H2O (9:1,v/v) S10 3000 Exitation wavelength ) . 300 nm u . 320 nm a ( 340 nm y 2000 t 360 nm i s n e t n I 1000 . l F 0 300 400 500 600 Wavelength (nm) 3+ Fig. S11 Graph for excitation wavelength variation of H2PPC with Al in MeOH-H2O (9:1,v/v) S11 5 LOD= 4.78 10-6 M ) 3x10 . u . a ( 5 y t 2x10 i s n Equation y = a + b*x e Weight No Weighting t Residual Sum 5.74915E9 5 of Squares n I 1x10 Pearson's r 0.97841 0.95195 . Adj. R-Square l Value Standard Error B Intercept 24443.01765 15756.23458 F B Slope 9879.70502 737.85329 0 0 10 20 30 40 [Al3+] M Fig. S12 plot for calculation of detection limit S12 (a) (b) 3+ Emission of H2PPC + Al in different solvent 3000 ) . u . a ( y 2000 t i s n e t n 1000 I . l F 0 H H N O F N O O C S M X e t e M D H M E M D (c) 3+ Fig. S13 (a) Absorption and (b) emission spectra of H2PPC and H2PPC with Al in different organic 3+ solvent (inset: corresponding image under UV-light, λ = 365 nm) (c) H2PPC+ Al in different water content of methanol under UV-light, λ = 365 nm. S13 3000 ) . u . a ( y t i s 2000 n e t n I . l F 1000 0.0 0.2 0.4 0.6 0.8 1.0 3+ [H2PPC]/([H2PPC]+[Al ]) Fig. S14 Jobs’ plot from fluorescence titration results Table-S1 Crystallographic data of H2PPC and 2 S14 Empirical C17H15N5O3 (H2PPC) C34 H28 Cu2 N12 O12 (2) formula Formula weight 337.34 923.78 Crystal system Tetragonal Triclinic Space group I41/a (No. 88) P-1 (No. 2) a/ Å 19.559(2) 8.4663(13) b/ Å 19.559(2) 9.2044(14) c/ Å 16.966(3) 11.8424(18) / 90 73.774(2) / 90 70.534(2) / 90 80.563(2) V/A3 6490.4(15) 832.9(2) Z 16 1 Density(D/gcm-3) 1.381 1.842 μ/mm-1 0.098 1.368 F(000) 2816 470 Temperature(K) 150 100 Θ range for data 1.6, 25.9 1.9, 28.0 collection/0 Dataset -23: 19 ; -23: 23 ; -20: -9: 11 ; -11: 11 ; -11: 15 20 Tot., Uniq. Data, 14751, 2939, 0.038 9623, 3719, 0.046 R(int) Observed data [I 1798 3071 > 2.0 σ(I)] Nref, Npar 2939, 239 3719, 280 R, wR2, S 0.0419, 0.1150, 1.01 0.0578, 0.1653, 1.10 Table-S2 Selected bond distances (Å) and angles (o) data for 2 Selected Bonds Value(Å) Selected Angles (o) Cu1-O3 1.897(2) O3-Cu1-O4 91.58(12) Cu1-O4 2.357(3) O3-Cu1-N1 98.08(13) Cu1-N1 2.053(4) O3-Cu1-N3 172.53(14) Cu1-N3 1.919(3) O3-Cu1-N5 95.48(13) Cu1-N5 2.010(4) O3-Cu1-O3# 84.69(11) Cu1-O3# 2.730(3) O4-Cu1-N1 97.53(13) O4-Cu1-N3 95.42(14) O4-Cu1-N5 83.01(13) O3#-Cu1-O4 171.62(9) N1-Cu1-N3 78.45(14) N1-Cu1-N5 166.41(13) O3#-Cu1-N1 90.43(12) N3-Cu1-N5 87.97(15) O3#-Cu1-N3 88.70(12) O3#-Cu1-N5 89.86(12) S15 Cu1-O3-Cu1# 95.31(12) Symmetry #=1-x,1-y,-z Table-S3 o Details of hydrogen bond distances (Å) and angles ( ) of H2PPC and complex-2 Compound D-H...A d(D-H) d(H...A) d(D...A) <(DHA) H2PPC N4-H4N O1 0.87(2) 2.167(19) 2.963(2) 152.6(16) O2-H2 N5 0.99(3) 1.73(3) 2.600(2) 145(3) Complex-2 N4-H4N O6 0.75(6) 2.32(6) 2.969(6) 145(6) O2-H2O O5 0.85(6) 2.15(6) 2.774(5) 129(6) Table S4: Ionic radii and ionic potential of relevant cations Cations Ionic radius a (Å) Ionic potential (Z/r) Hydrated radius b (Å) Ionic potential (z/r) Na+ 0.95 1.05 3.58 0.279 K + 1.33 0.75 3.31 0.302 Ba2+ 1.35 1.48 4.04 0.495 Ca2+ 0.99 2.02 4.12 0.485 Cd2+ 0.97 2.06 4.26 0.469 Co2+ 0.72 2.63 4.23 0.472 Cr3+ 0.64 4.68 4.61 0.650 Cu2+ 0.72 2.78 4.19 0.477 Zn2+ 0.74 2.70 4.30 0.465 Al3+ 0.50 6 4.75 0.631 Fe3+ 0.60 5 4.57 0.656 Hg2+ 1.02 1.96 - - Mg2+ 0.65 3.07 4.28 0.467 Mn2+ 0.80 2.50 4.38 0.456 Ni2+ 0.70 2.85 4.04 0.495 Pb2+ 1.32 1.51 4.01 0.498 S16 a L.
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