SUPPORTING INFORMATIONS a Novel Chemosensor Based On
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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 2018 SUPPORTING INFORMATIONS A novel chemosensor based on rhodamine and azobenzene moieties for selective detection of Al3+ ion Subhabrata Mabhai,a Malay Dolai,b Satyajit Dey,*,c Anamika Dhara, d Bhriguram Das,c Atanu Jana,*,e aDepartment of Chemistry, Mahishadal Raj College, East Midnapore, Mahishadal, West Bengal, Pin No. 721628, India bDepartment of Chemistry, Prabhat Kumar College, Contai, Purba Medinipur 721401, India cDepartment of Chemistry, Tamralipta Mahavidyalaya, East Midnapore, West Bengal, Pin No. 721636, India. E-mail: [email protected] dDepartment of Chemistry, Jadavpur University, Raja S. C. Mallick Road, Kolkata 700032, India. eDepartment of Chemistry, Indian Institute of Technology, Delhi, HauzKhas, New Delhi- 110016, India. E-mail: [email protected] Figure S1.1H NMR of 2-Hydroxy-5-((4-nitrophenyl) diazenyl) benzaldehyde Figure S2. Proton NMR of chemosensor ( L) NO2 N N HO NEt2 N O N O NEt2 Figure S3. 13C NMR of chemosensor ( L) Figure S4. Mass of the chemosensor ( L) Figure S5. Mass spectrum of L-Al3+ complex 1.4 L 1.2 0.10eqCu2+ 0.20eq Cu2+ 20 2+ 0.30eq Cu 2+ 1.0 0.40eq Cu 2+ e 0.50eq Cu c 2+ 0.60eq Cu n 0.8 2+ a 0.70 eq Cu b 2+ r 0.80eq Cu o 2+ 0.90eq Cu s 0.6 2+ 0 b 1.00eq Cu A 0.4 0.2 0.0 300 350 400 450 500 550 600 Wavelength (nm) Figure S6. UV-Vis spectral changes of L (20 µM) upon addition of Cu2+ ions in a HEPES o 2+ buffer [50 µM, C2H5OH-H2O (4:1, v/v, pH= 7.2)] at 25 C. [Cu ] = 0-20 µM 1.4 0M EDTA 1.2 1.0 e c n 0.8 a b r o 22M EDTA s 0.6 b A 0.4 0.2 0.0 300 350 400 450 500 550 600 Wavelength(nm) Figure S7. UV-Vis spectral changes of Cu2+ complex of L (20 µM) upon addition of EDTA o in HEPES buffer [50 µM, C2H5OH-H2O (4:1, v/v, pH= 7.2)] at 25 C. EDTA added = 0-22 µM 2.0 1.8 1.6 1.4 e c 1.2 n a b 1.0 r o s 0.8 b A 0.6 0.4 0.2 0.0 0.0 0.2 0.4 0.6 0.8 1.0 [Cu2+]/([Cu2+]+L) Figure S8. Job’s plot from absorbance data of L and Cu2+ with a total solution volume of 2 max ml in HEPES buffer [50 µM, C2H5OH-H2O (4:1, v/v, pH= 7.2)] at 25 °C λabs = 550 nm. 12 2 10 R = 0.98725 Ka = 1.45x104 (M-1) ] 0 8 A - A [ / 0 A 6 - x a m A 4 2 0 0 200 400 600 800 1000 1/[Cu2+]x 106 (M) Figure S9. Benesi-Hildebrand plot of L (20 μM) for Cu2+ determined by absorbance method in HEPES buffer [50 µM, C2H5OH-H2O (4:1, v/v, pH= 7.2)] at 25 °C Lactam Carbonyl Figure S10. IR Spectrum of chemosensor ( L) Conjugated amide Carbonyl Figure S11. IR Spectrum of L-Al3+ complex Figure S12: 13C NMR of ligand + Al3+ 140 120 ) . u . a 100 ( y t i s n 80 e t n i n o i 60 s o i m m 40 E 20 0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 [Al3+]/[L]+[Al3+] Figure S13. Job’s plot of Fluorescence intensity at 554 nm of L and Al3+ with a total concentration of 20 μM cations in HEPES buffer [50 µM, C2H5OH-H2O (4:1, v/v, pH= 7.2)] at 25 °C 12 R2 = 0.9823 10 -1 Ka = 7.033x 103(M) ) 0 8 A - A / 0 6 A - x a m 4 A 2 0 0 50 100 150 200 3+ 6 1/[Al] x10 (M) Figure S14. Benesi-Hildebrand plot of L (40 μM) for Al3+ determined by absorbance method in HEPES buffer [50 µM, C2H5OH-H2O (4:1, v/v, pH= 7.2)] at 25 °C 10000 Equation y = a + ) Adj. R-Sq 0.9764 . u . Value Standard a ( B Interce -937.4563 268.6022 y t i 8000 B Slope 140868.5 5304.707 s n e t n i 6000 e c n e c s r 4000 o u l f l a r 2000 g e t n i 0 0.00 0.02 0.04 0.06 0.08 Al3+ in g /ml Figure S15. The limit of detection (LOD) and limit of quantification (LOQ) were calculated using 3σ/S and 10σ/S methods, respectively. σ = the standard deviation of y-intercept of regression line, S = the slope of the calibration curve Table S1 The comparison of this probe with some other fluorescent probes for Al3+ Probe λem LOD Total Stokes Solvent Detection (nm) (μM) metal shift (V/V) method ions (nm) Ref. [1] 582 3.98 19 20 CH3CN/H2O (95:5) CHEF , Fluorescence quenching Ref. [2] 582 0.196 21 22 EtOH-H2O (1:1) --- Ref. [3] 550 0.183 17 16 CH3CN/H2O (9:1) CHEF,PET FRET Ref. [4] 556 3.26 17 17 H2O-EtOH (4:1) CHEF Ref. [5] 560 38.9 12 40 EtOH FRET Ref. [6] 558 4.17 16 28 DMF CHEF Ref. [7] 555 0.34 12 26 MeOH-H2O (1:1) CHEF Ref. [8] 490 0.42 18 25 CH3CN-H2O(50:50) ICT,CHEF Ref. [9] 513 2.40 13 139 DMSO ESIPT Ref. [10] 503 1.04 17 57 EtOH-H2O (9:1) -- Ref. [11] 538 0.29 13 58 DMSO ICT Ref. [12] 450 1.54 20 45 CH3CN–HEPES ICT buffer Our work 582 0.11 17 28 EtOH-H2O (4:1) CHEF, PET References 1 J. C. Peigang Dinga, Jinhui Wanga and C. Yufen Zhaoa-c and Yong Ye a, New J. Chem., 2015, 39, 342–348. 2 X. Bao, Q. Cao, Y. Xu, Y. Gao, Y. Xu, X. Nie, B. Zhou, T. Pang and J. Zhu, Bioorganic Med. Chem., 2015, 23, 694–702. 3 L. Fan, J. C. Qin, T. R. Li, B. D. Wang and Z. Y. Yang, Sensors Actuators, B Chem., 2014, 203, 550–556. 4 Y. Fu, X.-J. Jiang, Y.-Y. Zhu, B.-J. Zhou, S.-Q. Zang, M.-S. Tang, H.-Y. Zhang and T. C. W. Mak, Dalt. Trans., 2014, 43, 12624. 5 Y. Kim, G. Jang and T. S. Lee, ACS Appl. Mater. Interfaces, 2015, 7, 15649–15657. 6 M. Li, X. Zhang, Y. -hua. Fan and C. Bi, Luminescence, 2016, 31, 851–855. 7 R. Alam, R. Bhowmick, A. S. M. Islam, A. katarkar, K. Chaudhuri and M. Ali, New J. Chem., 2017, 41, 8359–8369. 8 R. Patil, A. Moirangthem, R. Butcher, N. Singh, A. Basu, K. Tayade, U. Fegade, D. Hundiwale and A. Kuwar, Dalton Trans., 2014, 43, 2895–9. 9 W. H. Ding, D. Wang, X. J. Zheng, W. J. Ding, J. Q. Zheng, W. H. Mu, W. Cao and L. P. Jin, Sensors Actuators, B Chem., 2015, 209, 359–367. 10 Y. Zhang, Y. Fang, N. Z. Xu, M. Q. Zhang, G. Z. Wu and C. Yao, Chinese Chem. Lett., 2016, 27, 1673–1678. 11 D. Karak, S. Lohar, A. Sahana, S. Guha, A. Banerjee and D. Das, Anal. Methods, 2012, 4, 1906. 12 S. Goswami, A. K. Das, K. Aich, A. Manna, H. K. Fun and C. K. Quah, Supramol. Chem., 2014, 26, 94–104..