Highly sensitive cyanide anion detection with a coumarin-spiropyran conjugate as a fluorescent receptor. Electronic Supplementary Information (ESI )
|
|
- Marshall Sharp
- 5 years ago
- Views:
Transcription
1 This journal is (c) The Royal Society of Chemistry 11 Highly sensitive cyanide anion detection with a coumarin-spiropyran conjugate as a fluorescent receptor Yasuhiro Shiraishi,* Shigehiro Sumiya, and Takayuki Hirai Research Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, saka University, Toyonaka , Japan shiraish@cheng.es.osaka-u.ac.jp Electronic Supplementary Information (ESI ) Contents page Experimental procedure... Synthesis... Nonlinear fitting of the fluorescence titration data... 3 Calculation details... 4 Table S1. Electronic transition properties of and CN Fig. S1 1 H NMR chart of... 6 Fig. S 13 C NMR chart of... 7 Fig. S3 EI-MS chart of... 8 Fig. S4 Change in absorption spectra of under 334 nm irradiation... 9 Fig. S5 Change in absorption spectra of under 55 or 38 nm irradiation... 1 Fig. S6 Effect of other anions on the fluorescence response of to CN Fig. S7 Change in fluorescence spectra of upon CN addition.. 1 Fig. S8 Absorption titration of with CN... 1 Fig. S9 ESI-MS chart of measured with CN Fig. S1 Fluorescence titration of with CN Fig. S11 Absorption and fluorescence spectra of 7-hydroxy-4-methylcoumarin Fig. S1 Fluorescence decays of 7-hydroxy-4-methylcoumarin and CN Cartesian coordinates of (MC) and CN S
2 This journal is (c) The Royal Society of Chemistry 11 Experimental procedure Absorption spectra were measured on an UV-visible photodiode-array spectrophotometer (Shimadzu; Multispec-15) equipped with a temperature controller S-17. [1] Fluorescence spectra were measured on a JASC FP-65 fluorescence spectrophotometer. Time-resolved emission decay analysis was carried out on a PTI-3 apparatus (Photon Technology International) using a Xe nanoflash lamp filled with N. [] Light irradiations were carried out with a Xe lamp (3 W; Asahi Spectra Co. Ltd.; MAX-3) equipped with 334 nm (light intensity: 69.1 mw m ), 38 nm (53.8 mw m ), and 55 nm (3.5 mw m ) band-pass filters, respectively. 1 H and 13 C NMR spectra were obtained by a JEL JNM-GSX7 Excalibur and JNM-AL4 spectrometer. EI- and ESI-MS analysis was performed by a JEL JMS 7 Mass Spectrometer. Synthesis Compound (1,3,3,4 -tetramethylspiro[indoline-,8 -H,8H-pyrano[,3-h]chromen--one]) N + H CH MeH reflux, 3 h N (66%) 1,3,3-Trimethyl--methylideneindole (161 mg,.93 mmol) and 8-formyl-7-hydroxy-4- methylcoumarin ( mg,.98 mmol) [3] were refluxed in MeH (5 ml) for 3 h under N. The resultant was concentrated by evaporation. The crude product was purified by silica gel column chromatography with CH Cl, affording as a white solid. Yield: mg, 66 %. 1 H NMR (7 MHz, acetone-d 6, TMS): δ = 7.53 (d, J = 8.7 Hz, 1H, ArH), 7.4 (d, J = 1.6 Hz, 1H, CCHCH ), (m, H, ArH), 6.8 (t, J = 7.4 Hz, 1H, ArH), 6.68 (d, J = 8.7 Hz, 1H, ArH), 6.6 (d, J = 7.6 Hz, 1H, ArH), 6.14 (d, J = 1. Hz, 1H, CCHCCH 3 ), 5.96 (d, J = 1.6 Hz, 1H, CCHCH ),.8 (s, 3H, NCH 3 ),.4 (d, J = 1. Hz, 3H, CCHCCH 3 ), 1.3 (s, 3H, C(CH 3 ) ), 1.19 ppm (s, 3H, C(CH 3 ) ); 13 C NMR (68 MHz, CDCl 3, TMS): δ = 16.6, 157., 15.7, 149.6, 147.7, 136., 17.5, 14.9, 1.4, 11.3, 119.5, 119.3, 11.8, 111.7, 111.3, 17.1, 16.8, 15.4, 5., 8.8, 5.8,., 18.7 ppm; EI-MS: m/z: calcd for C 3 H 1 N 3 : 359.; found: [M + ]; HRMS (EI + ): m/z: calcd for C 3 H 1 N 3 [M + ]: ; found: S
3 This journal is (c) The Royal Society of Chemistry 11 Nonlinear fitting of the fluorescence titration data [4] When assuming a 1:1 stoichiometry for interaction between and CN, the equilibrium is given by the following equation: K + CN ass CN (1) The association constant, K ass, is expressed as: K [ CN ] [ CN ] ass = = [ ][ CN ] ([ ] -[ CN ])([ CN ] -[ CN ]) () [ CN ], [], and [CN ] are the equilibrium concentrations of the CN species, free, and free CN, respectively. [] and [CN ] are the initial concentrations of and CN, respectively. The eq. is transformed to: [ CN ([ ] ] = + [ CN ] ) ([ ] + [ CN ] + ) 4[ ] [ CN ] K - ass Kass (3) Fluorescence intensity is given as follows: [5] λ I =Φ [ ] (4) λ λ I = Φ [ ] +Φ [ CN ] (5) CN I (6) λ λ max = Φ [ ] max+φ [ CN ] CN max I is the intensity of at 453 nm without anion under UV irradiation, I is the intensity of at 453 nm obtained with CN under UV irradiation, and I max is the intensity of at 453 nm in the presence of excess amount of CN under UV irradiation. Φ λ and Φ λ CN- are the fluorescence quantum yields for and CN. By means of eqs 4, 5 and 6, the following equation is obtained: I max I I I = [ max CN ] [ CN ] (7) With excess amount of CN, [. CN ] max is almost equal to []. The eq 7 can therefore be replaced as follows: I max I I I [ ] = [ CN ] (8) From eq. 3 and 8, the following equation is obtained: 3S
4 This journal is (c) The Royal Society of Chemistry 11 I max I 1 {([ ] [ ] ) ([ ] [ ] 1 I = I + + CN CN + ) 4[ ] [ CN ] } (9) [ ] K ass K ass The eq. 9 was used for fitting of the fluorescence titration data with CN. Calculation details Preliminary geometry optimizations were performed using the WinMPAC version 3. software (Fujitsu Inc.) at the semiempirical PM3 level. [6] The obtained structures were fully refined with tight convergence criteria at the DFT level with the Gaussian 3 package, [7] using the B3LYP/6-31G* basis set for all atoms. The excitation energies and the oscillator strength of each structure were calculated by the time-dependent density-functional response theory (TD-DFT) [8] at the same level of optimization using the polarizable continuum model (PCM) [9] with water as a solvent. Cartesian coordinates for the MC form of and CN species are summarized in the end of this ESI. [1] Y. Shiraishi, R. Miyamoto, T. Hirai, Langmuir 8, 4, [] Y. Shiraishi, Y. Tokitoh, T. Hirai, rg. Lett. 6, 8, [3] D. R. Bender, D. Kanne, J. D. Frazier, H. Rapoport, J. rg. Chem. 1983, 48, [4] J. Bourson, J. Pouget, B. Valeur, J. Phys. Chem. 1993, 97, [5] R. Yang, K. Li, K. Wang, F. Zhao, N. Li, F. Liu, Anal. Chem. 3, 75, [6] Y. Shiraishi, N. Saito, T. Hirai J. Am. Chem. Soc. 5, 17, [7] a) 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,. 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,. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. chterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain,. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. rtiz, 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. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 4. b) GaussView, Version 3.9, R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W. L. Hovell, R. Gilliland, Semichem, Inc., Shawnee Mission, KS, 3. [8] R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 19, [9] M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 55, S
5 This journal is (c) The Royal Society of Chemistry 11 Table S1. Calculated excitation energy (E), wavelength (λ), ground to excited state transition electric dipole moments (µ) and oscillator strength (f) for low-laying singlet state (S n ) of the MC form of and CN. (MC) S S 1 Main orbital transition (CIC a ) HM 1 LUM (.1) HM LUM (.6) S S HM LUM (.69) S S 3 HM 1 LUM (.66) CN S S 1 S S S S 3 HM LUM (.13) HM LUM (.61) HM LUM+1 (.19) HM LUM (.17) HM LUM+1 (.64) HM 3 LUM (.4) HM LUM (.11) HM 1 LUM (.63) E (ev) [λ (nm)].479 [51.67] [44.33] [397.78] 3.61 [38.7] [35.78] [34.85] a CI expansion coefficients for the main orbital transitions. µ (Debye) µ x µ y µ z µ tot f 5S
6 This journal is (c) The Royal Society of Chemistry 11 N Fig. S1 1 H NMR chart of (acetone-d 6, 7 MHz). 6S
7 This journal is (c) The Royal Society of Chemistry 11 N Fig. S 13 C NMR chart of (CDCl 3, 68 MHz). 7S
8 This journal is (c) The Royal Society of Chemistry 11 N Fig. S3 EI-MS chart of. 8S
9 This journal is (c) The Royal Society of Chemistry 11 a).3 5 min. A.1 b).3 min nm A. 58 nm t / min Fig. S4 (a) Time-dependent change in absorption spectra of (1 µm) measured in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under UV irradiation (334 nm) at 5 C. (b) Change in absorbance of 37 and 58 nm bands. 9S
10 This journal is (c) The Royal Society of Chemistry 11 a) A.3 min..1 A nm.1 58 nm min t / min b) A.3..1 min A nm.1 58 nm t / min 7 min Fig. S5 Time-dependent change in absorption spectra of (1 µm) measured in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under irradiation of (a) 38 nm and (b) 55 nm monochromatic light at 5 C. The measurements were carried out as follows: UV light (334 nm) was irradiated to the solution containing for 3 min. The spectral measurements were then started under irradiation of the respective monochromatic light. (Inset) Change in absorbance of 37 and 58 nm bands. 1S
11 This journal is (c) The Royal Society of Chemistry 11 a) 5 + CN - or + CN - + other anions 15 5 Fl 453 nm CN - + F - Fl b) CN - + Cl - CN - + Br - CN - + I - CN - + Ac - CN - + H P 4 - CN - + HS 4 - CN - + Cl 4 - CN - + N 3 - CN - + SCN - CN - Fig. S6 (a) Fluorescence spectra (λ ex = 39 nm) of (1 µm) measured with 5 equiv of CN together with 5 equiv of other respective anions in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under UV irradiation (334 nm) at 5 C. The fluorescence measurements were carried out after the solution was stirred for 3 min under UV irradiation. (b) Fluorescence intensity of the respective solutions. 11S
12 This journal is (c) The Royal Society of Chemistry 11 a) b) FI min FI 453 nm t / min FI min FI 453 nm t / min Fig. S7 Time-dependent change in the fluorescence spectra (λ ex = 39 nm) of (1 µm) measured after addition of (a) 1 equiv or (b) 5 equiv of CN in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under UV irradiation (334 nm) at 5 C. (Inset) Change in fluorescence intensity at 453 nm..3 A.3..1 [CN - ] µm A [CN - ] / [] 1 µm 37 nm 58 nm Fig. S8 Absorption titration of (1 µm) with CN in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under UV irradiation (334 nm) at 5 C. Each spectrum was obtained after stirring the solution for 3 min with UV irradiation. (Inset) Change in absorbance of 37 and 58 nm bands. 1S
13 This journal is (c) The Royal Society of Chemistry 11 [ + CN + n-bu 4 N + ] + m/z (Calculated:[ + CN + n-bu 4 N + ] + m/z 869.7) Fig. S9 ESI-MS chart of a MeCN solution containing of and equiv of n-bu 4 N + salt of CN obtained after UV irradiation (334 nm). 13S
14 This journal is (c) The Royal Society of Chemistry 11 Fl [CN - ] 5 µm Fl [CN - ] 1 µm.5 µm µm Fig. S1 Change in fluorescence spectra (λ ex = 37 nm) of (1 µm) during titration with CN in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under UV irradiation (334 nm) at 5 C. The spectra at each CN concentration were obtained after stirring the solution for 3 min under UV irradiation. The blue and red spectra were obtained with and.5 µm CN. A) 1. a b A (normalized).8.4 B) FI (normalized) a b Fig. S11 (A) Absorption spectra of (a) 7-hydroxy-4-methylcoumarin (1 µm) in a water/mecn mixture (8/ v/v; ph 1.8) and (b) (1 µm) measured with 5 equiv of CN in a water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) under UV irradiation (334 nm) at 5 ºC. (B) Normalized fluorescence spectra of (a) 7-hydroxy-4-methylcoumarin (λ ex = 3 nm) and (b) (λ ex = 39 nm) with 5 equiv of CN under UV irradiation at 5 ºC. The spectrum (b) was obtained after stirring the solution for 3 min under UV irradiation. 14S
15 This journal is (c) The Royal Society of Chemistry 11 a) 1 Intensity A.C t / ns W.R. species 7-hydroxy-4-methylcoumarin τ / ns (a / %) 4.1 (1) χ 1.59 b) 1 Intensity 1 1 A.C t / ns W.R. N CN τ / ns species (a / %) 4.1 CN - (1) χ 1.7 Fig. S1 (a) Fluorescence decay of 7-hydroxy-4-methylcoumarin in a water/mecn mixture (8/ v/v; ph 1.8) (λ ex = 337 nm, λ em = 448 nm). (b) Fluorescence decay of measured with 5 equiv of CN in a buffered water/mecn mixture (8/ v/v; CHES 1 mm, ph 9.3) (λ ex = 337 nm, λ em = 453 nm). The measurement was carried out after stirring the solution for 3 min under UV irradiation (334 nm). Shown as insert are the decay times (τ / ns) and the normalized pre-exponential factors (a). For judging the quality of the fit, chi-squares (χ ), autocorrelation functions (A.C.), and weighted residuals are also shown. 15S
16 This journal is (c) The Royal Society of Chemistry 11 Cartesian Coordinates (in Å) of the MC form of N (MC) C C C C C C H C H C H N H C H C H C H C H C H C H C H C H C H C H C H C H C H H H C H C H S
17 This journal is (c) The Royal Society of Chemistry 11 Cartesian Coordinates (in Å) of the CN species N CN CN C C C C C C N C H C H N H C H C H C H C H C H C H C H C H C H C H C H C H C H H H C H C H C H S
A phenylbenzoxazole-amide-azacrown linkage as a selective fluorescent receptor for ratiometric sening of Pb(II) in aqueous media
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,*
More informationA dominant homolytic O-Cl bond cleavage with low-spin triplet-state Fe(IV)=O formed is revealed in the mechanism of heme-dependent chlorite dismutase
Supplementary Information to: A dominant homolytic O-Cl bond cleavage with low-spin triplet-state Fe(IV)=O formed is revealed in the mechanism of heme-dependent chlorite dismutase Shuo Sun, Ze-Sheng Li,
More information3,4-Ethylenedioxythiophene (EDOT) and 3,4- Ethylenedioxyselenophene (EDOS): Synthesis and Reactivity of
Supporting Information 3,4-Ethylenedioxythiophene (EDOT) and 3,4- Ethylenedioxyselenophene (EDOS): Synthesis and Reactivity of C α -Si Bond Soumyajit Das, Pradip Kumar Dutta, Snigdha Panda, Sanjio S. Zade*
More informationDecomposition!of!Malonic!Anhydrides. Charles L. Perrin,* Agnes Flach, and Marlon N. Manalo SUPPORTING INFORMATION
S1 Decomposition!of!Malonic!Anhydrides Charles L. Perrin,* Agnes Flach, and Marlon N. Manalo SUPPORTING INFORMATION Complete Reference 26: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M.
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Highly Luminescent Tetradentate Bis-Cyclometalated Platinum Complexes: Design, Synthesis, Structure, Photophysics, and Electroluminescence Application Dileep A. K. Vezzu, Joseph
More informationSupplementary information
Supplementary information doi: 10.1038/nchem.287 A Potential Energy Surface Bifurcation in Terpene Biosynthesis Young J. Hong and Dean J. Tantillo* Department of Chemistry, University of California, Davis,
More informationPlanar Pentacoordinate Carbon in CAl 5 + : A Global Minimum
Supporting Information: Planar Pentacoordinate Carbon in CAl 5 + : A Global Minimum Yong Pei, Wei An, Keigo Ito, Paul von Ragué Schleyer, Xiao Cheng Zeng * Department of Chemistry and Nebraska Center for
More informationSupporting Information
Electronic Supplementary Material (ESI) for Energy & Environmental Science. This journal is The Royal Society of Chemistry 2014 Supporting Information Perylene Diimides: a Thickness-Insensitive Cathode
More informationTruong Ba Tai, Long Van Duong, Hung Tan Pham, Dang Thi Tuyet Mai and Minh Tho Nguyen*
Supplementary Information: A Disk-Aromatic Bowl Cluster B 30 : Towards Formation of Boron Buckyballs Truong Ba Tai, Long Van Duong, Hung Tan Pham, Dang Thi Tuyet Mai and Minh Tho Nguyen* The file contains
More informationPhotoinduced intramolecular charge transfer in trans-2-[4 -(N,Ndimethylamino)styryl]imidazo[4,5-b]pyridine:
Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences. This journal is The Royal Society of Chemistry and Owner Societies 2014 Photoinduced intramolecular charge transfer
More informationAluminum Siting in the ZSM-5 Framework by Combination of
Supplementary Information Aluminum Siting in the ZSM-5 Framework by Combination of High Resolution 27 Al NMR and DFT/MM calculations Stepan Sklenak,* a Jiří Dědeček, a Chengbin Li, a Blanka Wichterlová,
More informationSupporting Information. for. Silylation of Iron-Bound Carbon Monoxide. Affords a Terminal Fe Carbyne
Supporting Information for Silylation of Iron-Bound Carbon Monoxide Affords a Terminal Fe Carbyne Yunho Lee and Jonas C. Peters* Division of Chemistry and Chemical Engineering, California Institute of
More informationElectronic Supplementary information
Electronic Supplementary information SERS observation of soft C H vibrational mode of bifunctional alkanethiol molecules adsorbed at Au and Ag electrodes Inga Razmute-Razmė, Zenonas Kuodis, Olegas Eicher-Lorka
More informationMethionine Ligand selectively promotes monofunctional adducts between Trans-EE platinum anticancer drug and Guanine DNA base
Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2010 Supplementary Information Methionine Ligand selectively promotes monofunctional adducts between
More informationSpin contamination as a major problem in the calculation of spin-spin coupling in triplet biradicals
Supporting Information to the manuscript Spin contamination as a major problem in the calculation of spin-spin coupling in triplet biradicals P. Jost and C. van Wüllen Contents Computational Details...
More informationSynergistic Effects of Water and SO 2 on Degradation of MIL-125 in the Presence of Acid Gases
Supporting Information Synergistic Effects of Water and SO 2 on Degradation of MIL-125 in the Presence of Acid Gases William P. Mounfield, III, Chu Han,, Simon H. Pang, Uma Tumuluri, Yang Jiao, Souryadeep
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany From the alkyllithium aggregate [(nbuli) 2 PMDTA] 2 to lithiated PMDTA Carsten Strohmann*, Viktoria H. Gessner Institut für Anorganische Chemie,
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Aluminum Siting in Silicon-rich Zeolite Frameworks. A Combined High Resolution 27 Al NMR and QM/MM Study of ZSM-5 Stepan Sklenak,* Jiří Dědeček,
More informationSupporting Information For. metal-free methods for preparation of 2-acylbenzothiazoles and. dialkyl benzothiazole-2-yl phosphonates
Supporting Information For Peroxide as switch of dialkyl H-phosphonate: two mild and metal-free methods for preparation of 2-acylbenzothiazoles and dialkyl benzothiazole-2-yl phosphonates Xiao-Lan Chen,*,
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting Information Prenylated Benzoylphloroglucinols and from the Leaves of Garcinia multiflora
More informationElectronic supplementary information (ESI) Infrared spectroscopy of nucleotides in the gas phase 2. The protonated cyclic 3,5 -adenosine monophosphate
Electronic supplementary information (ESI) Infrared spectroscopy of nucleotides in the gas phase 2. The protonated cyclic 3,5 -adenosine monophosphate Francesco Lanucara, a,b Maria Elisa Crestoni,* a Barbara
More informationSupporting Information. Synthesis, Molecular Structure, and Facile Ring Flipping of a Bicyclo[1.1.0]tetrasilane
Supporting Information Synthesis, Molecular Structure, and Facile Ring Flipping of a Bicyclo[1.1.0]tetrasilane Kiyomi Ueba-Ohshima, Takeaki Iwamoto,*,# Mitsuo Kira*, #Research and Analytical Center for
More informationSupporting Information. spectroscopy and ab initio calculations of a large. amplitude intramolecular motion
Supporting Information Pseudorotation in pyrrolidine: rotational coherence spectroscopy and ab initio calculations of a large amplitude intramolecular motion Maksim Kunitski, Christoph Riehn, Victor V.
More informationPhosphine Oxide Jointed Electron Transporters for Reducing Interfacial
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Supporting Information Phosphine Oxide Jointed Electron Transporters for
More informationSuperacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles
Superacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles Yiliang Zhang, Daniel J. DeSchepper, Thomas M. Gilbert, and Douglas A. Klumpp Department of Chemistry
More informationSupplemental Material
Supplemental Material Sensitivity of Hydrogen Bonds of DNA and RNA to Hydration, as Gauged by 1 JNH Measurements in Ethanol Water Mixtures Marlon N. Manalo, Xiangming Kong, and Andy LiWang* Texas A&M University
More informationGroup 13 BN dehydrocoupling reagents, similar to transition metal catalysts but with unique reactivity. Part A: NMR Studies
Part A: NMR Studies ESI 1 11 B NMR spectrum of the 2:1 reaction of i Pr 2 NHBH 3 with Al(NMe 2 ) 3 in d 6 -benzene 24 h later 11 B NMR ESI 2 11 B NMR spectrum of the reaction of t BuNH 2 BH 3 with Al(NMe
More informationAli Rostami, Alexis Colin, Xiao Yu Li, Michael G. Chudzinski, Alan J. Lough and Mark S. Taylor*
N,N -Diaryl Squaramides: General, High-yielding Synthesis and Applications in Colorimetric Anion Sensing Ali Rostami, Alexis Colin, Xiao Yu Li, Michael G. Chudzinski, Alan J. Lough and Mark S. Taylor*
More informationMolecular Engineering towards Safer Lithium-Ion Batteries: A. Highly Stable and Compatible Redox Shuttle for Overcharge.
Supporting Information Molecular Engineering towards Safer Lithium-Ion Batteries: A Highly Stable and Compatible Redox Shuttle for vercharge Protection Lu Zhang, Zhengcheng Zhang,*, Paul C. Redfern, Larry
More informationElectronic Supplementary Information for:
Electronic Supplementary Information for: The Potential of a cyclo-as 5 Ligand Complex in Coordination Chemistry H. Krauss, a G. Balazs, a M. Bodensteiner, a and M. Scheer* a a Institute of Inorganic Chemistry,
More informationHighly sensitive detection of low-level water contents in. organic solvents and cyanide in aqueous media using novel. solvatochromic AIEE fluorophores
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Highly sensitive detection of low-level water contents
More informationUniversity of Groningen
University of Groningen Tuning the Temperature Dependence for Switching in Dithienylethene Photochromic Switches Kudernac, Tibor; Kobayashi, Takao; Uyama, Ayaka; Uchida, Kingo; Nakamura, Shinichiro; Feringa,
More informationEffect of Ionic Size on Solvate Stability of Glyme- Based Solvate Ionic Liquids
Supporting Information for: Effect of Ionic Size on Solvate Stability of Glyme- Based Solvate Ionic Liquids Toshihiko Mandai,,ǁ Kazuki Yoshida, Seiji Tsuzuki, Risa Nozawa, Hyuma Masu, Kazuhide Ueno, Kaoru
More informationDepartment of Chemistry, School of life Science and Technology, Jinan University, Guangzhou , China b
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information for A Br substituted phenanthroimidazole derivative with aggregation
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2008 Pyridine Catalyzed Stereoselective Addition of Acyclic 1,2-Diones to Acetylenic Ester: Synthetic and Theoretical
More informationSTRUCTURAL DETERMINATION OF A SYNTHETIC POLYMER BY GAUSSIAN COMPUTATIONAL MODELING SOFTWARE
STRUCTURAL DETERMINATIN F A SYNTHETIC PLYMER BY GAUSSIAN CMPUTATINAL MDELING SFTWARE AND NUCLEAR MAGNETIC RESNANCE SPECTRSCPY Kristen Entwistle*, Dwight Tshudy*, Terrence Collins** *Department of Chemistry,
More informationElectronic Supplementary Information (ESI) for Chem. Commun.
page S1 Electronic Supplementary Information (ESI) for Chem. Commun. Nitric oxide coupling mediated by iron porphyrins: the N-N bond formation step is facilitated by electrons and a proton Jun Yi, Brian
More informationA Redox-Fluorescent Molecular Switch Based on a. Heterobimetallic Ir(III) Complex with a Ferrocenyl. Azaheterocycle as Ancillary Ligand.
Supporting Information (SI) A Redox-Fluorescent Molecular Switch Based on a Heterobimetallic Ir(III) Complex with a Ferrocenyl Azaheterocycle as Ancillary Ligand. Fabiola Zapata, Antonio Caballero, Arturo
More informationSupporting Information. A rare three-coordinated zinc cluster-organic framework
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 0 Supporting Information A rare three-coordinated zinc cluster-organic framework with two types of second
More informationMetal Enhanced Interactions of Graphene with Monosaccharides. A Manuscript Submitted for publication to. Chemical Physics Letters.
Metal Enhanced Interactions of Graphene with Monosaccharides A Manuscript Submitted for publication to Chemical Physics Letters February 15, 2016 Carlos Pereyda-Pierre a and Abraham F. Jalbout b* a DIFUS,
More informationSupporting Information. O-Acetyl Side-chains in Saccharides: NMR J-Couplings and Statistical Models for Acetate Ester Conformational Analysis
Supporting Information -Acetyl Side-chains in Saccharides: NMR J-Couplings and Statistical Models for Acetate Ester Conformational Analysis Toby Turney, Qingfeng Pan, Luke Sernau, Ian Carmichael, Wenhui
More informationReversible intercyclobutadiene haptotropism in cyclopentadienylcobalt linear [4]phenylene
Reversible intercyclobutadiene haptotropism in cyclopentadienylcobalt linear [4]phenylene Thomas A. Albright, Sander Oldenhof, Oluwakemi A. Oloba, Robin Padilla and K. Peter C. Vollhardt * Experimental
More informationSupporting information on. Singlet Diradical Character from Experiment
Supporting information on Singlet Diradical Character from Experiment Kenji Kamada,,* Koji Ohta, Akihiro Shimizu, Takashi Kubo,,* Ryohei Kishi, Hideaki Takahashi, Edith Botek, Benoît Champagne,,* and Masayoshi
More informationSupporting Information. 4-Pyridylnitrene and 2-pyrazinylcarbene
Supporting Information for 4-Pyridylnitrene and 2-pyrazinylcarbene Curt Wentrup*, Ales Reisinger and David Kvaskoff Address: School of Chemistry and Molecular Biosciences, The University of Queensland,
More informationA Computational Model for the Dimerization of Allene: Supporting Information
A Computational Model for the Dimerization of Allene: Supporting Information Sarah L. Skraba and Richard P. Johnson* Department of Chemistry University of New Hampshire Durham, NH 03824 Corresponding Author:
More informationSupporting Information. {RuNO} 6 vs. Co-Ligand Oxidation: Two Non-Innocent Groups in One Ruthenium Nitrosyl Complex
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supporting Information {RuNO} 6 vs. Co-Ligand Oxidation: Two Non-Innocent Groups in
More informationA theoretical study on the thermodynamic parameters for some imidazolium crystals
Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research, 2015, 7(2):550-554 Research Article ISSN : 0975-7384 CODEN(USA) : JCPRC5 A theoretical study on the thermodynamic parameters
More informationSupporting Information
Supporting Information Oxygen Atom Transfer Reactions of Iridium and Osmium Complexes: Theoretical Study of Characteristic Features and Significantly Large Differences Between These Two Complexes Atsushi
More informationSupplementary Material
The Electronic Spectrum of the C s -C 11 H 3 Radical Dongfeng Zhao, 1 Harold Linnartz,,1 and Wim Ubachs 1 1 Institute for Lasers, Life, and Biophotonics, VU University Amsterdam, De Boelelaan 1081, NL
More informationMolecular Modeling of Photoluminescent Copper(I) Cyanide Materials. Jasprina L Ming Advisor: Craig A Bayse
Molecular Modeling of Photoluminescent Copper(I) Cyanide Materials Jasprina L Advisor: Craig A Bayse Department of Chemistry and Biochemistry, Old Dominion University, Hampton Boulevard, Norfolk, Virginia
More informationCalculating Accurate Proton Chemical Shifts of Organic Molecules with Density Functional Methods and Modest Basis Sets
Calculating Accurate Proton Chemical hifts of rganic Molecules with Density Functional Methods and Modest Basis ets Rupal Jain,, # Thomas Bally,, * and Paul Rablen $, * Department of Chemistry, University
More informationFerromagnetic Coupling of [Ni(dmit) 2 ] - Anions in. (m-fluoroanilinium)(dicyclohexano[18]crown-6)[ni(dmit) 2 ]
Supporting Information Ferromagnetic Coupling of [Ni(dmit) 2 ] - Anions in (m-fluoroanilinium)(dicyclohexano[18]crown-6)[ni(dmit) 2 ] Tomoyuki Akutagawa, *,, Daisuke Sato, Qiong Ye, Shin-ichiro Noro,,
More informationMotooka, Nishi, Fukuoka , Japan.
Electronic Supplementary Information A highly luminescent spiro-anthracenone-based organic light-emitting diode through thermally activated delayed fluorescence Keiro Nasu, a Tetsuya Nakagawa, a Hiroko
More informationSUPPLEMENTARY INFORMATION
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Novel B(Ar') 2 (Ar'') hetero-tri(aryl)boranes: a systematic study of Lewis acidity Robin
More informationSupporting Information
Supporting nformation Chromism Based on Supramolecular H-bonds Xiaowei Yu,, Chuanlang Zhan, *, Xunlei Ding, Shanlin Zhang, Xin Zhang, Huiying Liu, Lili Chen, Yishi Wu, Hongbing Fu, Shenggui He, *, Yan
More informationChina; University of Science and Technology, Nanjing , P R China.
Electronic Supplementary Information Lithium-doped MOF impregnated with lithium-coated fullerenes: A hydrogen storage route for high gravimetric and volumetric uptakes at ambient temperatures Dewei Rao,
More informationSupporting Information For
Supporting Information For Chemo-, Regio- and Stereoselective Synthesis of Polysusbtituted xazolo[3,2-d][1,4]oxazepin-5(3h)ones via a Domino oxa- Michael/aza-Michael/Williamson Cycloetherification Sequence
More informationConcerted halogen and hydrogen bonding in RuI 2 (H 2 dcbpy)(co) 2 ] I 2 (CH 3 OH) I 2 [RuI 2 (H 2 dcbpy)(co) 2 ]
Concerted halogen and hydrogen bonding in RuI 2 (H 2 dcbpy)(co) 2 ] I 2 (CH 3 OH) I 2 [RuI 2 (H 2 dcbpy)(co) 2 ] Matti Tuikka a, Mika Niskanen a, Pipsa Hirva a, Kari Rissanen b, Arto Valkonen b, and Matti
More informationSupporting Information
Missing Monometallofullerene with C 80 Cage Hidefumi Nikawa, Tomoya Yamada, Baopeng Cao, Naomi Mizorogi, Slanina Zdenek, Takahiro Tsuchiya, Takeshi Akasaka,* Kenji Yoza, Shigeru Nagase* Center for Tsukuba
More informationSupporting Information
Rich coordination chemistry of π-acceptor dibenzoarsole ligands Arvind Kumar Gupta, 1 Sunisa Akkarasamiyo, 2 Andreas Orthaber*,1 1 Molecular Inorganic Chemistry, Department of Chemistry, Ångström Laboratories,
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany The Donor-Acceptor Cyclopropanes as Three-Carbon Component in [4+3]-Cycloaddition. Reaction with 1,3-Diphenylisobenzofuran lga A. Ivanova,*
More informationSupplementary Information
Supplementary Information Enhancing the Double Exchange Interaction in Mixed Valence {V III -V II } Pair: A Theoretical Perspective Soumen Ghosh, Saurabh Kumar Singh and Gopalan Rajaraman* a Computational
More informationSupporting Information. Detection of Leucine Aminopeptidase Activity in Serum Using. Surface-Enhanced Raman Spectroscopy
Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2018 Supporting Information Detection of Leucine Aminopeptidase Activity in Serum Using Surface-Enhanced
More information1,5,2,4,6,8-dithiatetrazocine. Synthesis, computation, crystallography and voltammetry of the parent heterocycle. Supplemental Information
1,5,2,4,6,8-dithiatetrazocine. Synthesis, computation, crystallography and voltammetry of the parent heterocycle. Klaus H. Moock 1, Ken M. Wong 2 and René T. Boeré* 2 Moock Environmental Solutions Ltd.,
More informationSupporting Information
Supporting Information Hydrogen-bonding Interactions Between [BMIM][BF 4 ] and Acetonitrile Yan-Zhen Zheng, a Nan-Nan Wang, a,b Jun-Jie Luo, a Yu Zhou a and Zhi-Wu Yu*,a a Key Laboratory of Bioorganic
More informationNon-Radiative Decay Paths in Rhodamines: New. Theoretical Insights
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2014 Non-Radiative Decay Paths in Rhodamines: New Theoretical Insights Marika Savarese,
More informationScalable synthesis of quaterrylene: solution-phase
PT2 PT2 P 2PT......... Electronic Supplementary Information For Scalable synthesis of quaterrylene: solution-phase 1 PH NMR spectroscopy of its oxidative dication Rajesh Thamatam, Sarah L. Skraba and Richard
More informationLarge Hydroazaacene Diimides: Synthesis, Tautomerism, Halochromism, and Redox-switchable NIR Optics
Large Hydroazaacene Diimides: Synthesis, Tautomerism, Halochromism, and Redox-switchable NIR Optics Supplementary Information Kang Cai, Qifan Yan, and Dahui Zhao* Beijing National Laboratory for Molecular
More informationComputational Material Science Part II
Computational Material Science Part II Ito Chao ( ) Institute of Chemistry Academia Sinica Aim of Part II Get familiar with the computational methodologies often used and properties often predicted in
More informationSupporting Information
Mechanical Control of ATP Synthase Function: Activation Energy Difference between Tight and Loose Binding Sites Supporting Information Tamás Beke-Somfai* 1,2, Per Lincoln 1, Bengt Nordén* 1 1 Department
More informationSUPPORTING INFORMATION. Ammonia-Borane Dehydrogenation Promoted by a Pincer-Square- Planar Rhodium(I)-Monohydride: A Stepwise Hydrogen Transfer
S 1 SUPPORTING INFORMATION Ammonia-Borane Dehydrogenation Promoted by a Pincer-Square- Planar Rhodium(I)-Monohydride: A Stepwise Hydrogen Transfer from the Substrate to the Catalyst Miguel A. Esteruelas,*
More informationSupporting Information. S1: NMR Spectroscopy and resonance assignments ( 1 H, 13 C)
Supporting Information S1: NMR Spectroscopy and resonance assignments ( 1 H, 13 C) All NMR spectra were recorded at 25 C. Heteronuclear [ 1 H, 13 C] HSQC spectra were standard experiments in D 2 O (99.990%)
More informationSUPPLEMENTARY INFORMATION
DOI: 10.1038/NCHEM.1754 Caesium in high oxidation states and as a p-block element Mao-sheng Miao Materials Research Laboratory, University of California, Santa Barbara, CA 93106-5050, USA and Beijing Computational
More informationExperimental Evidence for Non-Canonical Thymine Cation Radicals in the Gas Phase
Supporting Information for Experimental Evidence for Non-Canonical Thymine Cation Radicals in the Gas Phase Andy Dang, Huong T. H. Nguyen, Heather Ruiz, Elettra Piacentino,Victor Ryzhov *, František Tureček
More informationSupporting Information
Theoretical examination of competitive -radical-induced cleavages of N-C and C -C bonds of peptides Wai-Kit Tang, Chun-Ping Leong, Qiang Hao, Chi-Kit Siu* Department of Biology and Chemistry, City University
More informationThe Activation of Carboxylic Acids via Self Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation
The Activation of Carboxylic Acids via Self Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation Mattia Riccardo Monaco, Daniele Fazzi, Nobuya Tsuji, Markus Leutzsch,
More informationOligo(N-aryl glycines): A New Twist on Structured Peptoids
Supporting Information ligo(-aryl glycines): A ew Twist on Structured Peptoids eel H. Shah, Glenn L. Butterfoss,, Khanh guyen, Barney Yoo, Richard Bonneau,, Dallas L. Rabenstein, and Kent Kirshenbaum*,
More informationLigand-to-Metal Ratio Controlled Assembly of Nanoporous Metal-Organic Frameworks
Electronic Supplementary Information for Ligand-to-Metal Ratio Controlled Assembly of Nanoporous Metal-Organic Frameworks Jian-Guo Lin, a Yan-Yan Xu, a Ling Qiu, b Shuang-Quan Zang, a Chang-Sheng Lu, a
More information1,4-Benzene-Bridged Covalent Hybrid of Triarylamine and Cyclometalated Ruthenium: A New Type of Organic-Inorganic Mixed-Valent System
Supporting Information for: 1,4-Benzene-Bridged Covalent Hybrid of Triarylamine and Cyclometalated Ruthenium: A ew Type of Organic-Inorganic Mixed-Valent System Chang-Jiang Yao, Ren-Hui Zheng, Qiang Shi,
More informationSupramolecular Aggregates with Distinct Optical. Properties from PDI Oligomers of Similar Structures
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2015 Electronic Supplementary Information Supramolecular Aggregates with Distinct Optical
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Reaction Dynamics of the Decaniobate ([H x Nb 10 O 28 ] (6-x)- ) Ion in Water Eric M. Villa, C. André Ohlin, Edina Balogh, Travis M. Anderson,
More information(1) 2. Thermochemical calculations [2,3]
1. Introduction The exploration of reaction mechanisms and reaction paths that cannot be measured directly during an experiment has nowadays become a daily routine for chemists to support their laboratory
More informationElectronic Supplementary Information. Electron Mobility for All-Polymer Solar Cells
Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers. This journal is the Partner Organisations 2018 Electronic Supplementary Information for Double B N Bridged Bipyridine-Containing
More informationTwo-Dimensional Carbon Compounds Derived from Graphyne with Chemical Properties Superior to Those of Graphene
Supplementary Information Two-Dimensional Carbon Compounds Derived from Graphyne with Chemical Properties Superior to Those of Graphene Jia-Jia Zheng, 1,2 Xiang Zhao, 1* Yuliang Zhao, 2 and Xingfa Gao
More informationSupporting Information. Fluorescent Coronene Monoimide Gels via H-bonding Induced Frustrated Dipolar Assembly
Supporting Information Fluorescent Coronene Monoimide Gels via H-bonding Induced Frustrated Dipolar Assembly Ankit Jain, K. Venkata Rao, Chidambar Kulkarni, Anjana George and Subi J. George* Supramolecular
More informationSupporting Information
Supporting Information Probing the Electronic and Structural Properties of Chromium Oxide Clusters (CrO ) n and (CrO ) n (n = 1 5): Photoelectron Spectroscopy and Density Functional Calculations Hua-Jin
More informationElectronic relaxation dynamics of PCDA PDA studied by transient absorption spectroscopy
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. his journal is the Owner Societies 06 Electronic Supplementary Information for Electronic relaxation dynamics of PCDA PDA
More informationSupporting Information
Quantum Chemistry Study of U(VI), Np(V) and Pu(IV,VI) Complexes with Preorganized Tetradentate Phenanthroline Amide Ligands Cheng-Liang Xiao, Qun-Yan Wu, Cong-Zhi Wang, Yu-Liang Zhao, Zhi-Fang Chai, *
More informationPreprint. This is the submitted version of a paper published in Journal of Computational Chemistry.
http://www.diva-portal.org Preprint This is the submitted version of a paper published in Journal of Computational Chemistry. Citation for the original published paper (version of record): Roca-Sanjuan,
More informationDFT and TDDFT calculation of lead chalcogenide clusters up to (PbX) 32
DFT and TDDFT calculation of lead chalcogenide clusters up to (PbX) 32 V. S. Gurin Research Institute for Physical Chemical Problems, Belarusian State University, Leningradskaya 14, 220006, Minsk, Belarus
More informationSupporting Information
Supporting Information Unimolecular Photoconversion of Multicolor Luminescence on Hierarchical Self-Assemblies Liangliang Zhu, Xin Li, Quan Zhang, Xing Ma, # Menghuan Li, # Huacheng Zhang, Zhong Luo, Hans
More informationDriving forces for the self-assembly of graphene oxide on organic monolayers
Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2014 Supporting Information Driving forces for the self-assembly of graphene oxide on organic monolayers
More informationA Fluorescent Heteroditopic Hemicryptophane Cage for the Selective Recognition of Choline Phosphate
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A Fluorescent Heteroditopic Hemicryptophane Cage for the Selective Recognition of Choline Phosphate
More informationTuning the electron transport band gap of bovine serum. albumin by doping with Vb12
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2019 Electronic Supplementary Information: Tuning the electron transport band gap of bovine serum albumin
More informationSupplementary Information:
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supplementary Information: Coordination and Insertion of Alkenes and Alkynes in Au III
More informationSupporting information
Supporting information Metal free Markovnikov type alkyne hydration under mild conditions Wenbo Liu, Haining Wang and Chao-Jun Li * Department of Chemistry and FQRNT Center for Green Chemistry and Catalysis,
More informationConcerted Attack of Frustrated Lewis Acid Base Pairs on Olefinic Double Bonds: A Theoretical Study
Supporting Information Concerted Attack of Frustrated Lewis Acid Base Pairs on Olefinic Double Bonds: A Theoretical Study András Stirling, Andrea Hamza, Tibor András Rokob and Imre Pápai* Chemical Research
More informationSupporting Information
Supporting Information ucleophile-catalyzed Additions to Activated Triple Bonds. Protection of Lactams, Imides, and ucleosides with MocVinyl and Related Groups Laura Mola, Joan Font, Lluís Bosch, Joaquim
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2015 Electronic Supporting Information Materials and methods 1,2-Bis[2,5-dimethyl(3-thienyl)]ethane-1,2-dione
More informationCICECO, Departamento de Química, Universidade de Aveiro, Aveiro, Portugal
Evidence for the Interactions Occurring between Ionic Liquids and Tetraethylene Glycol in Binary Mixtures and Aqueous Biphasic Systems Luciana I. N. Tomé, Jorge F. B. Pereira,, Robin D. Rogers, Mara G.
More information