Structural Effect of Thioureas on the Detection of Chemical Warfare Agent Simulants
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1 Structurl Effect of Thioures on the Detection of Chemicl Wrfre Agent Simulnts Seonggyun H, Minhe Lee, Hyun Ook Seo, b Sun Gu Song, Kyung-su Kim, Chn Heum Prk, Il Hee Kim, Young Dok Kim nd Chngsik Song* Deprtment of Chemistry, Sungkyunkwn University, 266, Seobu-ro, Jngn-gu, Suwon-si, Gyeonggi-do 16419, Republic of Kore. b Deprtment of Chemistry nd Energy Engineering, Sngmyung University, 2, Hongjimun 2-gil, Jongno-gu, Seoul 316, Republic of Kore. * E-mil: songcs@skku.edu. Contents Tble S1 Figure S1 Figure S2 Figure S3 Figure S4 Tble S2 Clcultion of FMx, equilibrium constnt (K) nd G o of receptors. Liner fitting of receptors from response curve of QCM mesurement: TUs 2 (), 4 (b) nd 8 (c). The schemtic digrm of MFC/bubbler system for QCM mesurement. The response curve of thioure-coted QCM sensor to DMMP vpor 6 ppm from TUs 1 to 9. The response curve of TUs 1 (), 2 (b), nd 8 (c) QCM sensor to different concentrtion of DMMP. Comprison of the men sensitivity nd the dsorbed mount of TU 4 with other mterils from references. S2 S3 S3 S4 S4 S5 Figure S5 Comprison of QCM tests with TU 4 for vrious gs molecules S5 Figure S6 QCM test of TU 4 depending on reltive humidity. S6 Figure S7-1 Figure S11 The NMR titrtion of 1, 2, 4 nd 8 (), nd NMR titrtion curve fter dding different concentrtion of DMMP (b). The NMR shift depending on the concentrtion of TUs from 1 to 5 mm: 1 (), 2 (b), 4 (c) nd 8 (d). S7-8 S9 Figure S12-17 The 1 H NMR nd 13 C NMR spectrum of 1, 2, 4 nd 8. S1-12 S1
2 Tble S1. Clcultion of FMx, equilibrium constnt (K) nd G o of receptors F Mx K (M -1 ) G o (kj/mol) TU 1 N/A N/A N/A TU TU TU Clcultion of ctive site ( FMx) nd equilibrium constnt (K) using Lngmuir isotherm eqution. The process of DMMP dsorption on ech receptor cn be expressed s follow ssuming the non-dissocitive dsorption of DMMP, S + A S A Eq 1 Where S is vcnt surfce sites of the receptor, A is DMMP molecules in gs phse, nd S A is the DMMP molecules dsorbed on the receptor surfce. If there is fixed number of surfce sites on the smple, the equilibrium constnt of DMMP dsorption (K) cn be defined in terms of the concentrtions of vcnt surfce sites [S], gsphse DMMP [A] nd DMMP dsorbed on receptor surfce [S A] s below. K = [S A].. Eq 2 [S][A] This cn be re-written using surfce coverge ( ) nd prtil pressure of DMMP (P) s follow, K = θ (1 θ)p.. Eq 3 Rerrngement of this eqution gives, θ = KP 1+KP Eq 4 nd tking the reciprocl of both side of eqution 4 gives, 1 = θ (1) Eq 5 K P The surfce coverge ( ) is the number of dsorbed molecules on the surfce divided by the number of molecules in monolyer covering the surfce sites nd it cn be re-expressed in terms of F s follow, θ = F F Mx....Eq 6 where FMx is the frequency chnge ( F) mesured during QCM experiments when the surfce of the receptor ws fully covered with monolyer of DMMP molecules. Combining Eq 5 nd 6 gives the liner reltionship between (1/ F) nd (1/P) s follow, 1 = ( 1 ) Eq 7 F F Mx K P F Mx The 1/ F t ech DMMP concentrtion ws plotted ginst the reciprocl of DMMP S2
3 concentrtion (1/P) for ech receptor cse nd ech set of dt ws fitted using liner lest squre regression method. The equilibrium constnt (K) of DMMP dsorption nd FMx vlues were derived from the slope (1/( FMx K)) nd Y-xis intercept (1/ FMx) of the line fitted to ech dt set. Further on, we hve clculted the Gibbs free energy chnge ( G o ) of DMMP dsorption for three receptor cses (2, 4, nd 8) using following eqution, G o = RT ln K Where R is the gs constnt (8.314 J/mol K), T is the bsolute temperture in Kelvins, nd K is the dsorption constnt. () D (1/delt F) Eqution y = + Adj. R-S.9948 Vlue Stndrd D Interce D Slope TU 2 liner fitting (b) D (1/delt F) Eqution y = + Adj. R-Sq.9988 Vlue Stndrd D Interce D Slope TU 4 liner fitting (c) D (1/delt F) Eqution y = + b Adj. R-Sq Vlue Stndrd D Intercep D Slope TU 8 liner fitting C (1/ppm) C (1/ppm) C (1/ppm) Figure S1. Liner fitting of receptors from response curve of QCM mesurement: TUs 2 (), 4 (b) nd 8 (c). Figure S2. The schemtic digrm of MFC/bubbler system for QCM mesurement. S3
4 F (Hz) F (Hz) , : DMMP blowing : N 2 blowing Time (s) Figure S3. The response curve of TU-coted QCM sensor to DMMP vpor 6 ppm from TUs 1 (yellow-green), 2 (light-purple), 3 (brown), 4 (red), 5 (ornge), 6 (nvy), 7 (pink), 8 (blue) nd 9 (green). () 12 ppm 12 ppm (b) 12 ppm 12 ppm. F (Hz) : DMMP blowing : N2 blowing F (Hz) : DMMP blowing : N2 blowing (c) : Delt F Tims (s) 12 ppm 12 ppm -8 : Delt F Time (s) : DMMP blowing -8 : N2 blowing : Delt F Time (s) Figure S4. The response curve of QCM sensor to different concentrtion of DMMP with 1 (), 2 (b), nd 8 (c). S4
5 Tble S2. Comprison of the men sensitivity nd the dsorbed mount of TU 4 with other mterils from references. Entry Smple Men Sensitivity Adsorbed Amount (S m) (DMMP g) Reference 1 HFHPB Fluorolcoholderivtives/SBA15 hybrids Titniumphthlocynines Poly(3-Methylthiophene) TU (Our work) n S m = 1 n f i (Hz/ppm) i C i Men sensitivity (S m vlues) f i : The frequency shift of the QCM C i : The concentrtion vlue F/ppm Acetone ACN EtOH Hex MeOH Toluene DMMP Figure S5. Comprison of QCM tests with TU 4 for vrious gs molecules. S5
6 : DMMP blowing : N 2 blowing : Delt F -3 DMMP RH 3.5% Delt F DMMP 98 ppm RH 7.5% RH 2% RH 3.5% RH DMMP 45% RH 7.5% DMMP RH 2% Time (s) DMMP RH 45% Figure S6. QCM test of TU 4 depending on reltive humidity. S6
7 () (b) 14 equiv. b 1.2 b (ppm) b 8 equiv ppm (f1) DMMP equiv.. Chemicl shift (ppm) Figure S7. The NMR titrtion of 1 (), NMR titrtion curve fter dding different concentrtion of DMMP (b). Clcultion of K nd G ws followed by ref 3 (Thordrson et l. J. Am. Chem. Soc. 214, 136, ). The detils were described therein. () (b) 21.5 equiv. 1.2 (ppm) equiv. 1. ppm (f1) DMMP equiv Chemicl shift (ppm) Figure S8. The NMR titrtion of 2 (), NMR titrtion curve fter dding different concentrtion of DMMP (b). Clcultion of K nd G ws followed by ref 3 (Thordrson et l. J. Am. Chem. Soc. 214, 136, ). The detils were described therein. S7
8 () (b) b 14 equiv. 1.2 b (ppm) b 2 1. ppm (t1) DMMP equiv equiv. 1.. Chemicl shift (ppm) Figure S9. The NMR titrtion of 4 (), NMR titrtion curve fter dding different concentrtion of DMMP (b). Clcultion of K nd G ws followed by ref 3 (Thordrson et l. J. Am. Chem. Soc. 214, 136, ). The detils were described therein. () b 16 equiv. (b) 1.2 b (ppm) DMMP equiv equiv. 1. ppm (t1) b Chemicl shift (ppm) Figure S1. The NMR titrtion of 8 (), NMR titrtion curve fter dding different concentrtion of DMMP (b). Clcultion of K nd G ws followed by ref 3 (Thordrson et l. J. Am. Chem. Soc. 214, 136, ). The detils were described therein. S8
9 Figure S11. The NMR shift depending on the concentrtion of TUs from 1 to 5 mm: 1 (), 2 (b), 4 (c) nd 8 (d). S9
10 Figure S12. The 1 H NMR spectrum of 2 (5 MHz, CDCl3). Figure S13. The 13 C NMR spectrum of 2 (125 MHz, CDCl3). S1
11 Figure S14. The 1 H NMR spectrum of 3 (5 MHz, CDCl3). Figure S15. The 13 C NMR spectrum of 3 (125 MHz, CDCl3). S11
12 Figure S16. The 1 H NMR spectrum of 4 (5 MHz, CDCl3). Figure S17. The 13 C NMR spectrum of 4 (125 MHz, CDCl3). S12
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