Vishal Kachwal a, Parvej Alam a, Hare Ram Yadav b, Saleem Pasha a, Angshuman Roy Choudhury b, Inamur Rahaman Laskar *a
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1 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 2017 Simple Ratiometric Push-Pull with Aggregation Induced Enhanced Emission Active Pyrene Derivative: Multifunctional and Highly Sensitive Fluorescent Sensor Vishal Kachwal a, Parvej Alam a, Hare Ram Yadav b, Saleem Pasha a, Angshuman Roy Choudhury b, Inamur Rahaman Laskar *a (a) Department of Chemistry, Birla Institute of Technology and Science, Pilani Campus, Pilani, Rajasthan, India; (b) Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER), Mohali, Sector 81, S. A. S. Nagar, Manauli PO, Mohali, Punjab , India; S1
2 Table of content Scheme 1 Frontier molecular orbital images of HOMO and LUMO energy levels of L (ligand) and Picric acid S3 showing inter molecular charge transfer Fig.S1. ( 1 H, 13 C) NMR spectrum (a, b) and HRMS (c), respectively for L S4 Fig. S2. Photoluminescence spectra of L in solution (1x10-3 M in DCM) and solid state (thin film). S4 Fig. S3. Absorption spectra of Pyrene, L and LH + in DCM (c = 10-5 M). S5 Fig. S4. Photoluminescence emission spectra of L and LH + in DCM (c = 10-3 M). S5 Fig. S5. Frontier molecular orbital images of HOMO and LUMO energy levels of L and LH + S5 Fig. S6. Cyclic voltammogram of L S6 Fig. S7. Normalized spectra of L and LH + S6 Fig. S8. (a) Absorption spectra of L (1x10-3 M) with different acid (1x10-3 M) concentration in methanol; S7 (b) PL intensity of L (1x10-3 M) with gradual increase of acid concentration and (c) Linear fitting of L with acid. Fig. S9. Photoluminescence spectra and image of L and LH + with gradual changing concentration, respectively S7 Fig.S10. (a) Photoluminescence spectra of intensity (I) values of L versus the compositions of the aqueous S8 mixtures concentration: 1x10-4 M; (b) Photoluminescence spectra of intensity (I) values of (LH + ) versus the compositions of the Aqueous mixtures, Concentration: 1x10-4 M (c) Absorption spectra of L in methanol/water mixtures with different water volume fractions (f w ) (d) Emission spectra of L in methanol/peg mixtures. Fig. S11. Packing diagram representing unit cell S8 Fig. S12. Powder XRD and Time resolved fluorescence spectra of L. S9 Fig. S13. (a) The absorption spectra of L (1x10-3 M) with gradual increase in the Picric Acid (PA) concentration S9 (b) Emission spectra of L (1x10-3 M) titrated with different concentration of PA (c) Linear fitting of L with PA Fig. S14. The spectral overlap between the emission of L and the absorption of PA was shown in inset S10 Fig. S15. (a) PL spectra of L with c = 10-3 M (methanol) upon the addition of 1 equivalent of different metal ions. S10,S11 (b) Column diagrams of the relative PL intensity of L with different metal ions at I 405 /I 530. (c) Image of L (c = 10-3 M) with 1 equivalent of different metal ions, (d) The absorption spectra of L (1x10-3 M) with gradual increase in the Al 3+ (1x10-3 M) concentration; (e) Emission spectra of L (1x10-3 M) titrated with different concentration of Aluminium nitrate; S11 (f) Linear fitting of L with the Al 3+ Fig. S16. HRMS of L with Al 3+ (a) [Al(L)+H] + (b) [Al(L) 2 +2H] +, (c) [Al(L) 3 +3H] S11,S12 Table S1 Comparison of sensitivity of detection of PA (Picric acid) (Literature reports vs present work). S13 Table S2 Comparison of sensitivity of detection of Al 3+ (Literature reports vs present work). S14 Table S3 The calculated values of L in different combination basis set. S14 Table S4 Details of the DFT calculation and coordinates of L S15 Table S5 Calculated major orbital excitation contributions (%), energy difference (in ev), obtained from electronic S16 transitions analysis with TDDFT (B3LYP) method for L Table S6 Calculated major orbital excitation contributions (%), energy difference (in ev),obtained from electronic S16 transitions analysis with TDDFT (B3LYP) method for LH+. Fig. S17 UV-Vis spectra from the TD-DFT calculated value (a,b,c) L and d is LH +. S16 Table S7 Crystal data and structure refinement for L S17 S2
3 Figures E LUMO = ev E LUMO = ev LUMO of L LUMO of PA e- e - e - HOMO of L E HUMO = ev HOMO of PA E HUMO = ev Picric Acid (PA) Scheme S1 Frontier molecular orbital images of HOMO and LUMO energy levels of L (ligand) and Picric acid showing intermolecular charge transfer; LUMO of picric acid is less than LUMO of L. (a) 1 H NMR (400 MHz, CDCl 3 ) δ 8.92 (d, J = 4.2 Hz, 1H), 8.42 (d, J = 9.3 Hz, 1H), 8.30 (d, J = 7.9 Hz, 1H), 8.22 (dd, J = 18.7, 7.8 Hz, 3H), (m, 4H), 7.93 (t, J = 8.6 Hz, 1H), 7.77 (d, J = 7.8 Hz, 1H), (m, 1H). Indicating by arrow sign: show the proton (-H) in pyridine S3
4 (b) 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , ,127.62, , , , , , , , , (c) Fig. S1 ( 1 Hand 13 C) NMR spectrum (a, b) and HRMS (c), respectively for L. Fig. S2 Photoluminescence spectra of L in DCM solution (1x10-3 M) and solid state (thin film) S4
5 (a) (b) Fig. S3 Absorption spectra a) L and LH + (DCM (c = 10-5 M)); b) L, LH + & Pyrene (Py) (DCM (c = 10-5 M)) shows red shifted absorbance after addition of H + into DCM solution of L. Fig. S4 Emission spectra of L and LH + in DCM (c = 10-3 M) (a) (b) E LUMO = ev E LUMO = ev E E= 3.63 ev E= 3.29 ev E HOMO = ev E HOMO = ev S5
6 L (LUMO) LH + (LUMO) Fig. S5 Frontier molecular orbital image a) HOMO and LUMO energy levels of L and b) HOMO and LUMO energy levels of LH +, calculated by using B3LYP/6-31 g ++(d, p) as implemented on Gaussian 09 Fig.S6 Cyclic voltammogram of L (a Pt wire counter electrode and a Pt disc working electrode; a Ag/AgCl pseudo reference electrode; dry acetonitrile containing L and 0.10 M LiClO 4 (100mg); ferrocene was used as internal reference). Scan rates: 50 mv/s; E ox onset is 1.05eV so experimental HOMO is 5.45 ev. (a) Fig. S7 (a) The normalized spectra of L on thin films (c = 10-3 M) showing reversibility in presence of acid-base (λ max = 433 nm for L and 473nm for LH + ); (b) Thin film image of L. (b) S6
7 (a) (b) (c) Fig. S8 (a) Absorption spectra of L (1x10-3 M) with different TFA concentration (1x10-3 M) in methanol (0.01eq)) (isosbestic point at (284 & 360) nm; (b) PL intensity of L (1x10-3 M) with gradual increase of acid concentration (isosbestic point wavelength = 456 nm; increasing concentration of TFA is marked in the spectrum) and (c) linear fitting of L with acid a) b) (c) (d) S7
8 Fig. S9 (a, b) Photoluminescence spectra of L and LH + with gradual changing concentration, respectively; (c, d) image of L and LH +, respectively with gradual changing concentration under excitation at 365 nm. (a) (b) (c) (d) Fig. S10 (a) Plot of intensity (I) values of L versus the compositions of the aqueous mixtures, concentration: 1x10-4 M; (b) Plot of Photoluminescence intensity (I) values of (LH + ) versus the compositions of the aqueous mixtures, concentration: 1x10-4 M; (c) Absorption spectra of L in methanol/water mixtures with different water volume fractions (f w ); (d) Emission spectra of L in methanol/peg mixtures. Fig. S11 Unit cell of L showing four molecules S8
9 i ii iii iv (a) Fig. S12 (a) Time resolved fluorescence spectra of L (a) L (0% water; black), L (30% water; red) and L (90% water, green). (b) Powder X-ray diffraction patterns of L recorded for various states collected from (i) powder form of L, (ii) powder collected from 10:90 % MeOH: water mixture (iii) powder after heating and (iv) obtained from single crystal data of L. (b) (a) (b) (c) S9
10 Fig. S13 (a) The absorption spectra of L in methanol (1x10-3 M) with gradual increase in the PA (Picric acid) (1x10-2 M) concentration (solution of PA was prepared in methanol); (b) Emission spectra of L (1x10-3 M) titrated with different concentration of PA; (c) linear fitting of L with PA. Fig. S14 Absorption spectra of PA and emission spectra of L in DCM; the spectral overlap between the emission of L and the absorption of PA was shown in inset. (a) (b) L Al(III) La(III) Yb(III) Eu(III) As(III) Fe(III) Cr(III) (c) (d) S10
11 (e) Fig S15 (a) The emission spectra of L upon addition different trivalent metal ion.(b) Pl Intensity comparison between L in the presence of Al(III) and Fe(III) (c) image of L (c = 10-3 M) with 1 equivalent of different trivalent metal ions, respectively; from left to right (under 365 nm UV lamp); (d) The absorption spectra of L (1x10-3 M) with gradual increase in the Al 3+ (1x10-3 M) concentration; (e) Emission spectra of L (1x10-3 M) titrated with different concentration of Aluminum nitrate; (f) Linear fitting of L with the Al 3+ (f) N AlH2 Molecular Weight: (a) S11
12 N N Al H 2H + (b) (c) Fig. S16 HRMS of L with Al 3+ (a) [Al(L)+H] + (b) [Al(L)2+2H] +, (c) [Al(L)3+3H] Table S1 Comparison of sensitivity of detection of PA (Literature reports vs present work). S12
13 S.NO Reference Detection Limit in solution 1 ACS Appl. Mater. Interfaces, 2011, 3, ppb 2. Chem. Commun., 2012, 48, ppb 3. Chem. Commun., 2012, 48, ppm 4. J. Mater. Chem., 2012, 22, ppb 5. Org. Lett., 2012, 14, ppb 6. Anal. Chim. Acta, 2015, 864, ppb 7. ACS Appl. Mater. Interfaces, 2013, 5, ppb and 1.9 ppb 8. J. Phy. Chem. C, 2013, 117, ppb 9. Langmuir, 2014, 30, M 10. J. Mater. Chem. C, 2014, 2, nm 11. Sens. Actuators, B, 2016, 229, nm 12. Talanta, 2017, 174, µm 13. Sens. Actuators, B, 2016, 234, nm 14. Sens. Actuators, B, 2017, 248, Sens. Actuators, B, 2016, 229, ppm 87 nm 107 nm 16. Sens. Actuators, B, 2017, 248, ppm 17 Sens. Actuators, B, 2017, 248, J. Photochem. Photobiol. Chemistry, 2017, 342, µM 16.51nM 19. Present Manuscript 56 nm (12 ppb) Table S2 Comparison of sensitivity of detection of Al 3+ (Literature reports vs present work). cc Reference Detection Limit in solution 1 Dalton Trans, 2015, 44, μm S13
14 2 J Fluoresc, 2016, 26, nm 3. Inorg. Chem, 2016, 55, nm 4 Sens. Actuators, B, 2017,239, μm 5. Anal. Chim. Acta, 2017, nm 6. J. Photochem. Photobiol. Chemistry, 2017, 332, Sens. Actuators, B, 2017, 244, nm 3.6 μm 8. Dyes Pigm., 2017, 139, μm 9. Chem. Commun, 2014, 50, μm 10. Present Manuscript 2.4 nm Table S3 Calulated HOMO, LUMO, Energy Gap and RMSD(Root Mean Square Deviation energy and optimization minium energy in different combination of basis set and functions. Basis set B3LYP CAM-B3LYP E (ev) HOMO LUMO HF- Energy RMSD energy E(eV) Homo LUMO HF- Energy 6-31g (d) * g (d,p) * g + (d) * g+ (d,p) * g++(d,p) *10-9 RMSD energy 8.23* *10-9 TABLE S4 Coordinates of L for DFT calculations using methanol nprocshared=1 %mem=2gb %chk=pyrene B3LYP ++D p opt.chk # opt b3lyp/6-31++g(d,p) scrf=(iefpcm,solvent=methanol) maxdisk=2gb geom=connectivity 0 1 X Y Z C C C C C C S14
15 C C C C C H C C C C C H H H H H H H H C C C C H C H H H N S15
16 Table S5: Calculated major orbital excitation contributions (%), energy difference (in ev), obtained from electronic transitions analysis with TDDFT (B3LYP) and CAM-B3LYP method for L.,Major orbital excitation contribution(%) Energy gap(ev) Calculated λ max (nm) oscillator strength in brackets (B3LYP) Calculated λ max (nm) oscillator strength in brackets ( CAM-B3LYP) Absorbance λ max (nm), molar absorptivity in brackets HOMO LUMO (96%) (0.560) 322 (0.6778) 374 (1750 L mole -1 cm -1 ) HOMO-1 LUMO (43.50%) (0.0060) 309 (0.0018) 345 (2250 L mole -1 cm -1 ) HOMO LUMO +1(60.36%) (0.0307) 255 (01429) 277 (3170 L mol -1 cm -1 ) HOMO LUMO +2 (60.36%) (0.0032) 249 (0.4113) 245 (21736 L mol -1 cm -1 ) Table S6: Calculated major orbital excitation contributions (%), energy difference (in ev), obtained from electronic transitions analysis with TDDFT (B3LYP) method for LH +. Major orbital excitation contribution (%) Energy gap (ev) Absorbance λ max (nm), molar absorptivity in brackets HOMO LUMO (95%) ( ) 406 (596 L mol -1 cm -1 ) HOMO LUMO +1 (76%) (0.1621) 354 ( 1540 L mole -1 cm -1 ) HOMO-1 LUMO ( 67%) (0.1135) 280 (1746 L mole -1 cm -1 ) HOMO-1 LUMO +2 (77%) (0.1150) 243 (1990 L mole -1 cm -1 ) [B3LYP/ 6-31 g ++ (d, p)] (a) [CAM-B3LYP/ 6-31 g ++ (d, p)] (b) S16
17 f f f f TD spectrum TD spectrum Wavelength, nm Wavelength, nm [B3LYP/6-31g (d, p)] (c) [B3LYP/6-31Gg ++ (d, p)] (d) TD spectrum TD spectrum Wavelength, nm Wavelength, nm Fig. S17 UV-Visible spectra from the TD-DFT calculated value (a,b,c) L and d is LH Table S7 Crystal data and structure refinement for L Empirical formula C 21 H 15 N Formula weight Temperature 293K Wavelength Bond precision: C-C = A Cell: a=3.9167(5) b=12.712(2) c=27.168(4) Alpha = 90 beta = (7) gamma=90 Calculated Reported Volume (3) (3) Space group P 21/c P 1 21/c 1 Hall group -P 2ybc -P 2ybc Mr Dx,g cm Z 4 4 µ (mm -1 ) F F000' h,k,l max 5,16,35 5,16,35 Nref T min,t max 0.990, ,1.000 T min ' S17
18 Correction method= # Reported T Limits: T min =0.896 T max =1.000 AbsCorr = MULTI-SCAN Data completeness= Theta(max)= R(reflections)= ( 1922) wr2(reflections)= ( 3076) S = Npar= 199 Reference 1 S. S. Pasha, P. Alam, A. Sarmah, R. K. Roy and I. R. Laskar, RSC Adv., 2016, 6, P. Alam, S. Dash, C. Climent, G. Kaur, A. R. Choudhury, D. Casanova, P. Alemany, R. Chowdhury and I. R. Laskar, RSC Adv., 2017, 7, Alam, P.; Kaur, G.; Kachwal, V.; Gupta, A.; Choudhury, A. R.; Laskar, I. R, J. Mater. Chem. C. 2015, 3 (21), Alam, P.; Kachwal, V.; Laskar, I. R., A.,Sens. Actuators B.2016, 228, S18
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