A phenylbenzoxazole-amide-azacrown linkage as a selective fluorescent receptor for ratiometric sening of Pb(II) in aqueous media
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1 This journal is The Royal Society of Chemistry 213 A phenylbenzoxazole-amide-azacrown linkage as a selective fluorescent receptor for ratiometric sening of Pb(II) in aqueous media Yasuhiro Shiraishi,* Yoshinao Matsunaga, Prannicha Hongpitakpong and Takayuki Hirai Research Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka , Japan. shiraish@cheng.es.osaka-u.ac.jp Electronic Supplementary Information (ESI ) CONTENTS Page Experimental... 2 References... 3 Table S1 Electronic transition properties Table S2 Protonation/stability constants of L Fig. S1 1 H NMR chart of L... 5 Fig. S2 13 C NMR chart of L... 6 Fig. S3 FAB MS chart of L... 7 Fig. S4 Absorption spectra of L measured with respective metal cations... 8 Fig. S5 Time-dependent change in fluorescence spectra of L with Pb Fig. S6 Effect of other metal cations on the Pb 2+ -induced fluorescence Fig. S7 Job s plot of L with Pb Fig. S8 ESI MS chart of L with Pb Fig. S9 Absorption and fluorescence spectra of L measured with Pb Fig. S1 Effect of ph on fluorescence spectra Fig. S11 IR spectra of L Fig. S12 Effect of water amount on fluorescence spectra Cartesian coordinates for L and L Pb S1
2 This journal is The Royal Society of Chemistry 213 Experimental Materials. All reagents were supplied from Wako, Sigma-Aldrich, and Tokyo Kasei and used without further purification. Perchlorate (Cu 2+, Na +, Hg 2+, Fe 2+, Mn 2+, Cr 3+, Fe 3+, Co 2+, Zn 2+, Mg 2+, Li +, Ni 2+, Cd 2+, K +, Ca 2+, Pb 2+ ) and tetrafluoroborate (Ag + ) salts were used as the metal cation source. Water was purified by the Milli-Q system. 1 was synthesized according to literature procedure. [1] Synthesis of L. 1 (86. mg,.3 mmol), 1-aza-18-crown 6-ether (92.2 mg,.35 mmol), KI (3 mg), and DIPEA (5 µl) were added to MeCN (4 ml), and the solution was refluxed for 12 h under N 2. The resultant was concentrated by evaporation and purified by silica gel column chromatography (CH 2 Cl 2 /MeOH, 11/1 v/v), affording L as a yellow solid (8. mg, 52%). 1 H NMR (4 MHz, CD 3 OD, TMS): δ = (m, 4H), (m, 22H), 7.31 (t, J = 7.1 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), 8.25 (dd, J = 1.37, 7.79 Hz, 1H), 8.7 (d, J = 8.24 Hz, 1H). 13 C NMR (1 MHz, CD 3 OD, TMS): δ = , , 15.82, , , , 129.8, 127.3, , 125.8, , 12.88, , , 71.19, 71.8, 71.4, 71.2, 69.38, 59.74, FAB MS: m/z calcd for C 27 H 35 N 3 O 7 : ; found: [M + Na + ]. HR MS (FAB): m/z calcd for [M + Na + ], ; Found, Measurements. UV vis absorption spectra were measured at 298 K on an UV visible photodiode array spectrophotometer (Shimadzu; Multispec 15) equipped with a temperature controller. [2] Fluorescence spectra were measured at 298 K on a JASCO FP 65 fluorescence spectrophotometer equipped with a temperature controller. FT-IR spectra were recorded at room temperature using a JASCO FTIR 61 spectrometer with a liquid sample cell with a CaF 2 window. [3] 1 H and 13 C NMR spectra were obtained by a JEOL JNM AL4 spectrometer using TMS as standard. FAB and ESI MS analysis was performed by a JEOL JMS 7 Mass Spectrometer. Potentiometric titration. The titrations were performed on a COMTITE 55 potentiometric automatic titrator (Hiranuma Co., Ltd.) with a glass electrode GE 11. [4,5] Aqueous solution (water/mecn, 1/1 v/v) containing S2
3 This journal is The Royal Society of Chemistry 213 L in the absence or presence of Pb(ClO 4 ) 2 (1 equiv) was kept under dry N 2 at 298 K. The titration was done at 298 ± 1 K in the presence of.15 M NaCl. The program HYPERQUAD was used for determination of protonation and stability constants. [6] K w (= [H + ] [OH ]) value used was (298 K). The stability constants used for Pb 2+ hydrolysis (298 K) were log K (Pb(OH)/Pb OH) = 8., (Pb(OH) 2 /Pb 2OH) = 17.41, (Pb(OH) 3 /Pb 3OH) = 28.6, (Pb 2 (OH)/2Pb OH) = 6.7, (Pb 3 (OH) 4 /3Pb 4OH)= 24.45, (Pb 4 (OH) 4 /4Pb 4OH) = 2.31, and (Pb 6 (OH) 8 /6Pb 8OH) = 43.61, respectively. [7] Computational details. Ab initio calculations were carried out with the Gaussian 3 program. [8] Geometry optimization was performed with the density functional theory (DFT) using the B3LYP function within the Gaussian 3 program. Calculations were carried out using the 6 31G* basis set for all atoms except for Pb 2+, for which Stuttgart/Dresden (SDD) [9] basis set with effective core potential was used. Electronic excitation energies and oscillator strengths were calculated with the time dependent density functional theory (TDDFT) at the same level of optimization using the polarizable continuum model (PCM) [1] with water as a solvent. Cartesian coordinates for respective compounds are summarized in the end of this ESI. References [1] M. Chen, X. Lv, Y. Liu, Y. Zhao, J. Liu, P. Wang and W. Guo, Org. Biomol. Chem., 211, 9, [2] D. Wang, R. Miyamoto, Y. Shiraishi and T. Hirai, Langmuir, 29, 25, [3] Y. Shiraishi, Y. Matsunaga and T. Hirai, Chem. Commun., 212, 48, [4] Y. Shiraishi, Y. Tokitoh, G. Nishimura and T. Hirai, Org. Lett., 25, 7, [5] Y. Shiraishi, Y. Tokitoh and T. Hirai, Chem. Commun., 25, [6] A. Sabatini, A. Vacca and P. Gans, Coord. Chem. Rev., 1992, 12, [7] C. F. Baes and R. E. Mesmer, The Hydrolysis of Cations, John Wiley, New York, [8] Gaussian 3, Revision B.5, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, Jr., J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. S3
4 This journal is The Royal Society of Chemistry 213 Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 24. [9] D. Andrae, U. Häußermann, M. Dolg, H. Stoll and H. Preuß, Theor. Chim. Acta, 199, 77, [1] M. Cossi, V. Barone, R. Cammi and J. Tomasi, Chem. Phys. Lett., 1996, 255, Table S1. Calculated excitation energy (E), wavelength (λ), and oscillator strength (f) for low-laying singlet state (S n ) of L and L Pb 2+. Species Main orbital transition (CIC a ) E / ev λ / nm f L S S 1 HOMO LUMO (.719) S S 2 HOMO 1 LUMO (.6474) L Pb 2+ S S 1 HOMO LUMO (.6658) S S 2 HOMO 1 LUMO (.42379) a CI expansion coefficients for the main orbital transitions. Table S2. Protonation/stability constants of L. a Reaction log K L + H + = LH 6.4 ±.19 L + Pb 2+ = L Pb ±.25 a Measurements were carried out in an aqueous solution (water/mecn; 1/1 v/v) at 298 K in the presence of.15 M NaCl. S4
5 This journal is The Royal Society of Chemistry 213 Fig. S1 1 H NMR chart of L in CD 3 OD (4 MHz). S5
6 This journal is The Royal Society of Chemistry 213 Fig. S2 13 C NMR chart of L in CD 3 OD (1 MHz). S6
7 This journal is The Royal Society of Chemistry 213 Fig. S3 FAB MS chart of L. S7
8 This journal is The Royal Society of Chemistry Hg 2+ Pb 2+ A.2 L only other cations 3 4 λ / nm Fig. S4 Absorption spectra of L (2 µm) measured in a buffered water/mecn mixture (1/1 v/v; HEPES 1 mm; ph 7.) with each respective metal cation (1 equiv). a) 6 1 s b) 6 L + Pb 2+ FI /au 4 2 s Fl 58 nm λ / nm t / s Fig. S5 (a) Time-dependent change in fluorescence spectra (λ ex = 311 nm) of L (2 µm) measured in a buffered water/mecn mixture (1/1 v/v; HEPES 1 mm; ph 7.), after addition of 1 equiv of Pb 2+. (b) Change in fluorescence intensity at 58 nm. S8
9 This journal is The Royal Society of Chemistry 213 a) 6 Pb 2+ only Pb 2+ + other cations FI /au 4 2 Pb 2+ + Cu 2+ Pb 2+ + Hg 2+ L only λ / nm b) 6 FI 58 nm 4 2 none Pb 2+ + Hg 2+ Pb 2+ + Cu 2+ Pb 2+ + Co 2+ Pb 2+ + Cr 3+ Pb 2+ + Cd 2+ Pb 2+ + Fe 2+ Pb 2+ + Fe 3+ Pb 2+ + Li + Pb 2+ + Mn 2+ Pb 2+ + Na + Pb 2+ + Ni 2+ Pb 2+ + Mg 2+ Pb 2+ + Ca 2+ Pb 2+ + K + Pb 2+ + Zn 2+ Pb 2+ + Ag + Pb 2+ Fig. S6 (a) Fluorescence spectra (λ ex = 311 nm) of L (2 µm) measured in a buffered water/mecn mixture (1/1 v/v; HEPES 1 mm; ph 7.) with 1 equiv of Pb 2+ together with 1 equiv of other respective metal cation. (b) Fluorescence intensity at 58 nm. 3.5 Fl 58 nm 2 1 Fig. S7 Job s plot of L with Pb 2+ obtained by fluorescence measurements (λ ex = 311 nm). Total concentration of L and Pb 2+ is 2 µm..5 1 [Pb 2+ ] / ([Pb 2+ ]+[L]) S9
10 This journal is The Royal Society of Chemistry 213 [L+ Pb 2+ H + ] + m/z 72.1 (Calculated: [L+ Pb 2+ H + ] + m/z 72.22) Fig. S8 ESI MS chart of a water/mecn (1/1 v/v) mixture containing of L and 1 equiv of Pb(ClO 4 ) 2. a).4 (2) L + Pb 2+ b) 6 (2) L + Pb 2+ A.2 (1) L only (3) L + Pb 2+ + EDTA FI /au 4 (3) L + Pb 2+ + EDTA (1) L only λ / nm λ / nm Fig. S9 (a) Absorption and (b) fluorescence spectra (λ ex = 311 nm) of L (2 µm) in a buffered water/mecn mixture (1/1 v/v; HEPES 1 mm; ph 7.) measured (1) without cations, (2) with Pb 2+ (1 equiv), and (3) after addition of EDTA (2 equiv) to the sample (2). S1
11 This journal is The Royal Society of Chemistry L + Pb 2+ Fl 58 nm 4 2 L ph 6 LH L 1 6 LH L Pb 2+ L Fl 58 nm 2.5 Fl 58 nm ph ph Fig. S1 (Top) Effect of ph on the fluorescence spectra of L measured in a water/mecn (1/1 v/v) mixture with or without 1 equiv of Pb 2+. (Bottom) Relationship between the fluorescence intensity and the mole fraction distribution of species determined by potentiometric titration (Table S2). S11
12 This journal is The Royal Society of Chemistry 213 L only 1667 Pb Wavenumber / cm 1 Fig. S11 IR spectra of L (2 mm) measured at 298 K in a D 2 O/MeCN (1/1 v/v, ph 7.) mixture with and without Pb 2+ (1 equiv). a) water/mecn (4/1 v/v) b) water/mecn (1/4 v/v) 1 1 L + Pb 2+ L + Pb 2+ + Cu 2+ FI /au 5 L + Pb 2+ L + Pb Cu L + Pb 2+ + Hg 2+ L FI /au 5 L + Pb 2+ + Hg 2+ L only λ / nm λ / nm Fig. S12 Fluorescence spectra (λ ex = 311 nm) of L (2 µm) in a buffered water/mecn mixture (HEPES 1 mm; ph 7.) with solvent composition, measured with 1 equiv of Pb 2+ together with 1 equiv of Cu 2+ or Hg 2+. S12
13 This journal is The Royal Society of Chemistry 213 Cartesian coordinates (in Å) of L C C H C C H C O H C C H C C H C C H N C H C O H O C H C C H C O H C C H C C H C H H C H H N H H C H H O H H C H H C H H N H H O H H C H H O H H S13
14 This journal is The Royal Society of Chemistry 213 Cartesian coordinates (in Å) of L Pb 2+ complex C C H C O H C C H C C H C C H C C H N O H C C H O C H C O H C C H C C H C H H C H H C H H N H H C H H O H H C H H C H H N H H O H H C H H O H Pb C S14
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