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1 Electronic upplementary Material (EI) for Photochemical & Photobiological ciences. This journal is The Royal ociety of Chemistry and wner ocieties 214 upplementary Information elective and sensitive fluorescence-shift probes based on two dansyl groups for mercury(ii) ion detection Li-Jun Ma,* Jialun Liu, Lefang Deng, Meili Zhao, Zhifu Deng, Xutian Li, Jian Tang and Liting Yang Table of contents Pages Fig. 1 Job s plot and binding constant of 2 and Hg Fig. 2 Job s plot and binding constant of 1 and Hg Fig. 3 The ph influence on the selectivity of compound Fig. 4 The ph influence on the selectivity of compound Fig. Reversibility study of 1 and 2 with EDTA Fig. 6 Atomic numbering of Table. 1 Hydrogen chemical shifts (δ, in ppm) for 1 and its complex with Hg (II).... Fig. 7 The 1 H MR spectra of 1 with addition of Hg 2+ in MeH-d 4 :D 2 (2:1, V/V)....6 Fig. 8 Proposed coordination model for 1-Hg Fig. 9 The EI-M spectra of 2 and 2+Hg( 3 ) Fig. 1 Atomic numbering of Table. 2 Hydrogen chemical shifts (δ, in ppm) for 2 and its complex with Hg (II) Fig. 11 The 1 H MR spectra of 2 with addition of Hg 2+ in MeH-d 4 :D 2 (7:2, V/V) Fig. 12 Proposed coordination model for 2-Hg
2 8 6 (A) (B) I-I 4 2 [ Hg 2+ ] /1-6 M [Hg] 2+ /( [2]+[Hg] 2+ ) ( I-I ) /( I MAX -I ) Fig.1 (A) Fluorescence intensity changes of peak at 498 nm of 2 and Hg 2+ with a total concentration of 2. M in ah 2 P 4 /a 2 HP 4 buffered solution (methanol- 1%, ph 6.), indicating a 2:1 stoichiometric ration of 2: Hg 2+ (λ ex = 34 nm, λ em = 498 nm). (B) Estimation of binding constant for 2 and Hg 2+, the plot was calculated based on the equation and a 2:1 binding model (λ ex = 34 nm, λ em = 498 nm) 12 1 (A) 6 (B) I-I 7 I /(I-I ) [ Hg 2+ ] /( [1]+[ Hg 2+ ] ) 1..x1 1.x1 6 1.x1 6 2.x1 6 [Hg 2+ ] -1 /M Fig.2 (A) Fluorescence intensity changes of peak at 498 nm of 1 and Hg 2+ with a total concentration of 2. M in ah 2 P 4 /a 2 HP 4 buffered solution (methanol- 2%, ph 6.), indicating a 1:1 stoichiometric ration of 1: Hg 2+ (λ ex = 34 nm, λ em = 498 nm). (B) Estimation of binding constant for 1 and Hg 2+, the plot was calculated based on the equation and a 2:1 binding model (λ ex = 34 nm, λ em = 498 nm) The ph influence on the selectivity of compound 1 and 2-2 -
3 ( a ) ( a ) Intensity Wavelength/nm ph Peak hift/nm ph Fig.3 (a) Fluorescence spectra of 2 (. M) in ah 2 P 4 /a 2 HP 4 buffered solution (Methanol-1 %) under different ph value excitated at 34 nm (without the addition of Hg( 3 ) 2 ); (b) Fluorescence spectra of 2 (. M) in ah 2 P 4 /a 2 HP 4 buffered solution (Methanol-1 %) under different ph value excitated at 34 nm. The blue-shift of maximum emission peak upon addition of. M Hg( 3 ) Intensity ph Peak hift/nm Wavelength/nm ph Fig.4 (a) Fluorescence spectra of 1 (. M) in ah 2 P 4 /a 2 HP 4 buffered solution (Methanol-2 %) under different ph value excitated at 34 nm (without the addition of HgCl 2 ); (b) Fluorescence spectra of 2 (. M) in ah 2 P 4 /a 2 HP 4 buffered solution (Methanol-2 %) under different ph value excitated at 34 nm. The blue-shift of maximum emission peak upon addition of. M Hg( 3 ) 2. Reversibility study of 1 and 2 with EDTA -3 -
4 ( a ) Intensity Hg( 3 ) 2 2+Hg( 3 ) 2 +EDTA Wavelength/nm Intensity 33 1+Hg( 3 ) Hg( 3 ) 2 +EDTA Wavelength/nm Fig. (a) Fluorescence spectra of 2 (. M) in ah 2 P 4 /a 2 HP 4 buffered solution (Methanol-1 %) upon addition of Hg( 3 ) 2 (2. M) and EDTA (2. M) at an excitation of 34 nm; (b) Fluorescence spectra of 1 (. M) in ah 2 P 4 /a 2 HP 4 buffered solution (Methanol-2 %) upon addition of Hg( 3 ) 2 (2. M) and EDTA (2. M) at an excitation of 34 nm. -4 -
5 MR date of 1 and 1-Hg 2+ H H Fig.6 Atomic numbering of 1 Table 1 Hydrogen chemical shifts (δ, in ppm) for 2 and its complex with Hg (II); atomic numbering is shown in Fig Hg 2+ (2:1,m/m) 1-Hg 2+ (1:1,m/m) Δλ(ppm) Δλ(ppm) H3(1) H1(13) H6(19) H2(14) H(17) H4(16) H7(18) H8(12) H9(11) H
6 ( c ) ( a ) ppm Fig.7 elected region of the 1 H MR spectra of (a) 1, (b)1/hg 2+ (2:1), (c) 1/Hg 2+ (1:1) in MeH-d 4 :D 2 (7:2, V/V). -6 -
7 H 3 C CH 3 H 3 C CH3 H + CH - Hg 2+ CH CH Hg 2+ CH - H 3 C CH 3 H + H 3 C CH 3 Fig. 8 Proposed coordination model for 1-Hg
8 ( a ) 2 [ 2 ] + H g 2 + [ 2 + H + ] + [ 2 + a + ] + The EI-M spectra of 2 and 2+Hg( 3 ) Relative Abundance m/z Relative Abundance m/z Fig.9 The EI-M spectra of 2 in the absence (a) and presence (b) of Hg( 3 ) 2 in CH 3 H. -8 -
9 ( a ) MR date of 2 and 2-Hg (II) H C CH 3 H Fig.1 Atomic numbering of 2 Table 2 Hydrogen chemical shifts (δ, in ppm) for 2 and its complex with Hg (II); atomic numbering is shown in Fig Hg 2+ (:1,m/m) 2-Hg 2+ (2:1,m/m) δ 1 /ppm δ 2 /ppm H12 H H11 H H H H H H H H H H H H6 H H H H2 H
10 ( c ) ( a ) ppm Fig.11 elected region of the 1 H MR spectra of (a) 2, (b) 2/Hg 2+ (:1), (c) 2/Hg 2+ (2:1) in MeH-d 4 :D 2 (2:1, V/V). -1 -
11 H 3 C H + CH 3 H 3 C H + CH 3 HC - C CH 3 - Hg 2+ CH H 3 C C - - H 3 C H + CH 3 H3C CH3 H + Fig. 12 Proposed coordination model for 2-Hg
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