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1 Electronic Supplementary Information Acid induced acetylacetonato replacement in biscyclometalated iridium(iii) complexes Yanfang Li, a,b Yang Liu * a,c and Ming Zhou* a,c a Suzhou Institute of Nano-Tech and Nano-Bionics, Chinese Academy of Sciences, 398 Ruoshui Road, Suzhou Industrial Park, Jiangsu, , P. R. China. b Graduate School of the Chinese Academy of Sciences. Beijing, 149, P. R. China c SunaTech Inc. biobay, Suzhou Industrial Park, Jiangsu, , P. R. China mzhou27@sinano.ac.cn yliu27@sinano.ac.cn
2 List of Scheme and Figures 1. UV-Vis spectrum of acetylacetone in acetonitrile...fig. S H NMR investigation of the transition from Ir(L) 2 (acac) to [Ir(L) 2 (MeCN) 2 ][OTf] upon the addition of TFA-d...Fig. S2 3. UV-Vis and emission spectra of Ir (btp) 2 acac with/without Hg(ClO 4 ) 2...Fig. S3 4. Emission spectra of complex 2-4 upon addition of Hg(ClO 4 ) 2....Fig. S4 5. Hg 2+ sensing mechanisms proposed in Ref. 23 (A) and Ref. 24 (B)...Scheme S H NMR studies on the sufur-containing compounds (2 mm in CD 3 CN) upon the addition of HgCl 2....Fig. S5 7. Emission spectra of complex Ir(MDQ) 2 acac upon addition of different amounts TFA and Hg(ClO 4 ) 2..Fig. S6 8.Emission spectra of 1 (2 µm) in MeCN solution by addition of different amounts of Hg(ClO 4 ) 2 in HEPES aqueous solution..fig. S7 9. Cyclic voltammograms of 6 (5 µm) in CH 3 CN solution.....fig. S9 1. Cyclic voltammograms of 1-3 in the absence and presence of Hg(ClO 4 ) 2 and TFA Figs. S8 & S1 11. ESI-MS study of the products of 1-2 mixed with 2 equiv of Hg(ClO 4 ) Figs. S11 & S Study on the chemical kinetics figs. S13 S H NMR, 13 C NMR and Mass Spectra of Ir(III) complexes figs. S16 S3 S1
3 Absorbance (a.u.) 2 M acetylacetone Fig. S1. UV-Vis spectrum of acetylacetone (2 µm) in CH 3 CN solution Fig. S2. 1 H NMR investigation of the transition from Ir(L) 2 (acac) to [Ir(L) 2 (MeCN) 2 ][OTf] upon the addition of TFA-d of 2 and 3 equiv. B: from 1 to 6; C: from 2 to 7; (all complexes dissolved in CD 3 CN, ca. 4 mm). S2
4 nm 61 nm Absorbance E.q. of Hg(ClO 4 ) nm 475 nm Emission (a.u) E.q. of Hg(ClO 4 ) 2 ex =44 nm Fig. S3. UV-Vis and emission spectra of Ir(btp) 2 acac (2 µm) in CH 3 CN solution with/without Hg nm 2 Emission (a.u.) nm nm 561 nm nm 3 4 Emission (a.u.) 1 5 Emission (a.u.) Fig. S4. Emission spectra of complex 2-4 (2 µm) in CH 3 CN solution upon addition of different amounts Hg(ClO 4 ) 2. S3
5 Scheme S1. Hg 2+ sensing mechanisms proposed in Ref. 23 (A) and Ref. 24 (B). Fig. S5. 1 H NMR studies on the sufur-containing compounds (2 mm in CD 3 CN) upon the addition of HgCl 2. (A) thiophene, (B) thiophene plus 1 equiv. of HgCl 2 and (C) thiophene plus 2 equiv. of HgCl 2 ; (D) btp, (E) btp plus 1 equiv. of HgCl 2 and (F) btp plus 2 equiv. of HgCl 2 ; (G) bt, (H) bt plus 1 equiv. of HgCl 2 and (I) bt plus 2 equiv. of HgCl 2. S4
6 2 Ir(MDQ) 2 acac+ TFA 62 nm 62 nm Ir(MDQ) 2 acac+ Hg(ClO 4 ) 2 Emission (a.u.) 1 Emission (a.u.) Fig. S6. Emission spectra of complex Ir(MDQ) 2 acac (2 µm) in CH 3 CN solution upon addition of different amounts TFA and Hg(ClO 4 ) 2. λ ex = 445 nm E.q. of Hg(ClO 4 ) 2 in HEPES Emission (a.u.) E.q. + 3 E.q. + 4 E.q Fig. S7. Emission spectra of 1 (2 µm) in MeCN solution by addition of different amounts of Hg(ClO 4 ) 2 in HEPES aqueous solution (λ ex = 44 nm) (A) I ( ) Hg(ClO 4 ) 2.48 V.9 V (B) I ( ) TFA.48 V.9 V E (V) E (V) Fig. S8. Cyclic voltammograms of 1 (5 µm) in CH 3 CN solution in the absence and presence of (A) Hg(ClO 4 ) 2 and (B) TFA. All measurements were carried out in a one-compartment cell under N 2 gas, equipped with a platinum working electrode, a platinum wire counter electrode, and a Ag/AgNO 3 (.1 M) reference electrode. The supporting electrolyte was.1 M tetrabutyl ammonium hexafluorophosphate (Bu 4 NPF 6 ) CH 3 CN solution. The potential scan rate was 5 mv/s -1. S5
7 V I ( ) V.85 V E (V) Fig. S9. Cyclic voltammograms of 6 (5 µm) in CH 3 CN solution The supported electrolyte was.1 M tetrabutyl ammonium hexafluorophosphate (Bu 4 NPF 6 ) CH 3 CN solution. The potential scan rate was 5 mv/s -1. I ( ) Hg(ClO 4 ) 2.54 V I ( ) TFA.54 V E (V) 3.7 V 3+ Hg(ClO 4 ) E (V) 3.69 V 3+ TFA I ( ) E (V) I ( ) E (V) Fig. S1. Cyclic voltammograms of 2 and 3 (5 µm) in CH 3 CN solution in the absence and presence of Hg(ClO 4 ) 2 and TFA. The experimental conditions were same as that described in Fig. S8. S6
8 Fig. S11. ESI-MS study of the product of Ir(btp) 2 acac mixed with 2 equiv of Hg(ClO 4 ) 2. The ESI-MS is identical to that of 6, i,e., [Ir(btp) 2 (MeCN) 2 ][OTf] synthesized in this work (see Fig. S23). Fig. S12. ESI-MS study of Ir(piq) 2 acac mixed with 2 equiv of Hg(ClO 4 ) 2. The ESI-MS is identical to that of 7, i,e., [Ir(piq) 2 (MeCN) 2 ][OTf] synthesized in this work (see Fig. S27). These studies shown in Fig. S11 & S12 were carried out in order to find any clue of the so-called Hg 2+ - Ir(btp) 2 (acac) complex. S7
9 Study on the chemical kinetics: The chemical kinetics experiment was measured quantitatively by monitoring the change in absorbance at 476 nm. The cyclometalated Ir(III) complex, Ir(btp) 2 acac, was dissolved in acetonitrile to obtain a stock solution (15 μm). To 2.5 ml of the Ir(III) complex solution in a quartz cuvette, 25 µl of the aqueous solution of TFA ( M) was added and consequently examined by UV-Vis absorption spectroscopy. The reaction was investigated at five different temperatures (3 o C, 35 o C, 4 o C, 45 o C and 5 o C) and the UV Vis absorption spectra were recorded as Figure S13. The concentration of Ir(btp) 2 acac solution during the reaction was determined spectrophotometrically at 476 nm according to calibration curve (Fig. S14). Ir(btp) 2 acac + TFA + MeCN [Ir(btp) 2 (MeCN) 2 ][CF 3 COO] + Hacac C : a b C t : a-x b-x x x Ir(btp) 2 acac dissociation reaction is estimated as a second-order reaction. The kinetics of the reaction d[ P] dx was calculated according to equation (1): Rate k[ Ir( btp) 2 acac][ TFA] k( a x)( b x), dt dt the second-order rate constant k was calculated as the equation (2): different temperatures were shown in Table S1. A plot of 1 b( a k ln t( a b) a( b x) x). The k at ln k versus 1/T was linear with negative slope E a and positive intercept (see Fig. S15). According to Arrhenius equation (3): ln k lna -, the apparent RT activation energy (E a ) was evaluated as 51.6 kj mol -1. In the mean time, according to the equation (4): lnk =-ΔG /RT=-ΔH /RT+ΔS /R, ΔH and ΔS were evaluated as 51.6 kj mol -1 and 41.7 kj mol -1 respectively. Absorbance nm 3 o C Ir(btp) 2 acac 2 min 4 min 6 min 8 min 1 min Absorbance Ir(btp) 2 acac 1 min 2 min 3 min 4 min 5 min 35 o C S8
10 Absorbance Ir(btp) 2 acac 1 min 2 min 3 min 4 min 5 min 4 o C Absorbance Ir(btp) 2 acac 1 min 2 min 3 min 4 min 5 min 45 o C Absorbance Ir(btp) 2 acac 1 min 2 min 3 min 4 min 5 min 5 o C Fig. S13. Absorbance changes with time and temperatures during the reaction of complex Ir(btp) 2 acac (15 µm) in CH 3 CN solution with 5 eq TFA. y=64x A 476 nm C Fig. S14. Representative calibration curve of A 476 nm versus of the concentration of Ir(btp) 2 acac in CH 3 CN solution. T ( o C) k (mol -1 L min -1 ) Table. S1. k values at different temperatures. S9
11 3. y=-6.276x lnk /T Fig. S15. Plot of lnk vs 1/T for Ir(btp) 2 acac Fig. S16. 1 H NMR spectrum of 3, i.e., Ir(bt) 2 (acac) in CD 3 CN S1
12 Fig. S17. 1 H NMR spectrum of 4, i.e., Ir(ppy) 2 (acac) in DMSO-d 6 Fig. S18. 1 H NMR spectrum of 8, i.e., [Ir(bt) 2 (MeCN) 2 ][OTf] in CDCl 3. S11
13 Fig. S19. 1 H NMR spectrum of 1, i.e., Ir(btp) 2 (acac) in CDCl 3 Fig. S2. 13 C NMR spectrum of 1, i.e., Ir(btp) 2 (acac) in CDCl 3 S12
14 Fig. S21. 1 H NMR spectrum of 6, i.e., [Ir(btp) 2 (MeCN) 2 ][OTf] in CD 3 CN Fig. S C NMR spectrum of 6, i.e., [Ir(btp) 2 (MeCN) 2 ][OTf] in CD 3 CN S13
15 Fig. S23. MS spectra of 6, i.e., [Ir(btp) 2 (MeCN) 2 ][OTf] Fig. S24. 1 H NMR spectrum of 2, i,e., Ir(piq) 2 (acac) in DMSO-d 6 S14
16 Fig. S25. 1 H NMR spectrum of 7, i,e., [Ir(piq) 2 (MeCN) 2 ][OTf] in CDCl Fig. S26. 1 H NMR spectrum of 7, i,e., [Ir(piq) 2 (MeCN) 2 ][OTf] in CDCl 3 S15
17 Fig. S27. MS spectrum of 7, i,e., [Ir(piq) 2 (MeCN) 2 ][OTf]. Fig. S28. 1 H NMR spectrum of 5, i.e., [Ir(btp) 2 (phen)][cl] in CDCl 3 S16
18 Fig. S C NMR spectrum of 5, i.e., [Ir(btp) 2 (phen)][cl] in CDCl 3 Fig. S3. MS spectrum of 5, i.e., [Ir(btp) 2 (phen)][cl]. S17
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