Isatin phenylhydrazones: Anion enhanced photochromic behaviour
|
|
- Hester Johnston
- 5 years ago
- Views:
Transcription
1 Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences. This journal is The Royal Society of Chemistry and Owner Societies 2015 Electronic Supplementary Information (ESI) Isatin phenylhydrazones: Anion enhanced photochromic behaviour Marek Cigáň a, *, Klaudia Jakusová a, Martin Gáplovský b, Juraj Filo a, Jana Donovalová a, Anton Gáplovský a a Faculty of Natural Sciences, Institute of Chemistry, Comenius University, Mlynská dolina CH-2, SK Bratislava, Slovakia; s: cigan@fns.uniba.sk (M.C.); jakusova@fns.uniba.sk (K.J.); donovalova@fns.uniba.sk (J.D.); horvathm@fns.uniba.sk (M.H.); sokolik@fns.uniba.sk (R.S.); gaplovsky@fns.uniba.sk (A.G.) b Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, SK Bratislava, Slovakia; gaplovsky@fpharm.uniba.sk (M.G.) * cigan@fns.uniba.sk 1
2 EXPERIMENTAL SECTION Supporting information Synthesis General Scheme: Synthesis of 1 and 2 Z-isomers in EtOH. (E)-isatin N 2 -phenylhydrazones 1 and 2: (Z)-3-(phenylhydrazono)indolin-2-one Z1: Obtained from phenylhydrazine (0.76g) in 78% yield (1.24g), 1 H NMR (300 MHz, DMSO-d 6 ), δ: (s, 1H), (s, 1H), 7.56 (d, J = 7.5 Hz, 1H), (m, 4H), 7.25 (td, J = 7.7, 1.2 Hz, 1H), 7.05 (m, 2H), 6.93 (d, J = 7.8 Hz, 1H). 13 C NMR (75 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). Anal. Calcd. for C 14 H 11 N 3 O (237.26) C, 70.87; H, 4.867; N, Found C, 71.71; H, 4.71; N, (Z)-3-(phenylhydrazono)-1-methylindolin-2-one Z2: Obtained from phenylhydrazine (0.69g) in 83% yield (1.30g), 1 H NMR (300 MHz, (CD 3 ) 2 CO), δ: (s, 1H), 7.63 (dd, J = 7.5, 0.5 Hz, 1H), (m, 5H), 7.13 (ddd, J = 7.6, 0.9 Hz, 1H), (m, 2H), 3.32 (s, 3H). 13 C NMR (75 MHz, DMSO), δ: (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). Anal. Calcd. for C 15 H 13 N 3 O (251.28) C, 71.70; H, 5.21; N, Found C, 71.82; H, 5.18; N,
3 Titration experiments Apparent association constant K ass determinations Equation (1) was rewritten to the following form for nonlinear fit: A = A0 + c1 *(P1- A0 ) * ( c0 + x +1/P2 - ( c0 + x +1/P2)^2-4 * c0 * x ), (2) where: c 0 = , c 1 = 1/2c 0 = , parameter P1 = A lim, parameter P2 = K ass and x = c A-. The A 0 value was fixed to the absorbance value A for x = 0. The large difference in constants c 0, c 1 and the x- data range led rescaling the nonlinear function (x and fitted parameter 1/P2 by a factor of 10 4 ). Following this modification, the standard non-linear least-squares Nelder-Mead minimization method was employed to determine fitting parameters P1 and P2. 60,61 Three different wavelengths were used to K ass determination of Z1 and Z2 (470 nm, 475 nm and 480 nm). 3
4 Light initiated E-Z and Z-E isomerization Quantum yield determination The Z-E isomerization quantum yield ( E-Z ) of isatin phenylhydrazone Z-isomers Z1 and Z2 in DMF solution was determined by equations (6) and (7) at low Z-E conversion (to eliminate the effect of back E-Z photoisomerization): 62 φ Z E = c t c 0 dc t I a dt 0 = Δc t I a dt 0 c = A λ ε (6); Z λ (7) where: c is the concentration change in Z-isomer, I a is Z-isomer absorbed photon flux at the irradiation wavelength using a monochromatic light source, A is the absorbance change at irradiation wavelength using a monochromatic light source, Z is Z-isomer molar extinction coefficient at irradiation wavelength using a monochromatic light source and t is irradiation time. Because only Z- isomers were isolated from the reaction mixture, the Z-isomer extinction coefficient at 405 nm was determined by Eq. (8): ε Z 405 = A 405 c Z. (8) The Z-isomer absorbed photon flux I a during Z-E isomerization at irradiation wavelength = 405 nm and incident Z-isomer concentration c 0 was calculated by Eq. (9): 62 I a,z 405 = I 0[ 1 10 [ε Z 405 (c 0 Δc)] ]. (9) The incident photon flux I 0 was determined by 2-nitrobenzaldehyde (2-NB) as chemical actinometer, according to Eq. (10): 63 k I 0 = 2.303ε o NB 405 φ o NB 405 l, (10) where: o-nb405 is the molar extinction coefficient of 2-NB at irradiation wavelength 405 nm, o-nb405 is the quantum yield of 2-NB photodegradation at irradiation wavelength, l is the path length and k is the 2- NB first-order photodegradation slope plotted under low-light-absorbing conditions: 63 4
5 (11) ln( [o NB] ) t = kt [o NB] 0. Quantum yield of the A-form transformation (Ф A ) induced by light (465 nm LED sources) was determined by Eqs. (12)-(14): (13) φ A = c t c 0 dc A t I a dt 0 = Δc A t I a dt 0 (12); c A = A λ ε A λ where: c is the concentration change in A-form (E-isomer of azo A-form), I a is A-form absorbed photon flux at the irradiation wavelength using a monochromatic light source, A is the absorbance change at irradiation wavelength using a monochromatic light source, Z is A-form molar extinction coefficient at irradiation wavelength using a monochromatic light source and t is irradiation time. Because the amount of transformed Z-isomer to A-form after the strongly basic anion addition is known, the A-form concentration change was determined by Eq. (13) at low A- to B-form conversion (to eliminate the effect of back B-A thermal transformation that is approximately 10-times slower compared to A-B photochemical transformation). The A-form extinction coefficient at 465 nm was calculated as: A465 = A 465 /c A465 ; where: c A = c Z(without F - ) - c, c = A 375 / Z375 and Z375 = A 375 /c Z(without F - ). The A-form absorbed photon flux I a at irradiation wavelength = 465 nm and incident A-form concentration c A0 was calculated by Eq. (14): I a,a 465 = I 0[ 1 10 [ε A 465 (c A0 Δc)] ]. (14) The incident photon flux I 0 at 465 nm was determined by ferrioxalate (FE) actinometry, according to Eq. (15): 64 ( da FE 390 ) 1 I a, FE 465 dt φ FE 465. ε FE 390. l I 0 = = 1 10 A FE A FE 465 (15), where: a, FE465 is ferrioxalate actinometer absorbed photon flux, A FE is ferrioxalate absorbance at corresponding wavelength using a monochromatic light source, FE390 is ferrioxalate molar extinction coefficient at 390 nm, FE465 is quantum yield of ferrioxalate photochemical conversion and l is the path 5
6 length. Ferrioxalate absorbance at 465 nm (A FE was measured by Ocean Optics SD2000 spectrophotometer. 6
7 Photochemical A/B conversion Because the A-form extinction coefficients at 465 nm for both phenylhydrazones 1 and 2 are known, the amount of photochemically transformed azo A-form to form B was calculated by Eq. (16): c A A 465 A 465 = ~ = ε B 465 ε A 465 1/4ε A 465 ε A 465 (16) A 465 1/3ε A 465 ε A 465 = A 46 3/4ε where the molar extinction coefficients of corresponding B-forms ( B465 ) were extrapolated from the A / B ratio of long-wavelength transitions in calculated UV-Vis spectra of A- and B-forms (M062x 6-31+g(dp) level). The long-wavelength transitions relates to a charge-transfer transition in A-form and n-π* transition in B-form, respectively. Initial concentrations of A-form in solution (c A ) were calculated according to the following equation: c A = c Z (without F ) c, (17) where Δc = ΔA 375 / Z375 and Z375 = A 375 /c - Z(without F ). The photoisomerization extent therefore increases from 20-30% conversion to 84% and 77% after F - anion addition to Z1 and Z2 solution, respectively. If ε B 465 = 1/5ε A 465 is assumed, then photoisomerization extents are 79% and 71%. 7
8 SUPPORTING SCHEMES AND FIGURES Fig. S1. 1 H NMR spectrum of Z2 in DMSO-d 6 before and after irradiation with light of 405 nm wavelength (T = K). Scheme S1. Assumed structure of Z1 dimer at higher concentrations. 8
9 Fig. S2. Calculated relative Gibbs free energies of E1 and Z1 isomers (keto forms) and their enol E1- enol and Z1-enol conformers at the M062x 6-31+g(dp) level in vacuum (T = K; TS transition state). 9
10 E1 Z1 Scheme S2. Calculated geometries of E1 and Z1 isomer keto-forms at the M062x 6-31+g(dp) level in vacuum (T = K). Quantum-chemical calculations failed to detect direct TS from E1 E-isomer. 10
11 E1-enol Z1-enol E1-enolZ1-enolTS Scheme S3. Calculated geometries of E1 and Z1 isomer enol-forms (E1-enol and Z1-enol) and corresponding transition state (TS) for their mutual E-Z (Z-E) thermal isomerization in vacuum at the at the M062x 6-31+g(dp) level (T = K). 11
12 Fig. S3. The time-dependent absorbance changes of isatin phenylhydrazone Z1 at 450nm and 400 nm ( M) after addition of M TBA + F - in DMF (c Z1 = M; c F - = M; T = K; t 1/2 is the reaction half-life calculated from mono-exponential fit of absorbance change at 450 nm). Fig. S4. The Z1-anion interaction pseudo first-oder rate constant (k) dependence on the F - anion concentration (c Z1 = M; T = K). 12
13 Fig. S5. Time-dependet UV-Vis spectrum changes of isatin phenylhydrazone Z1 solution after the TBA + OH - addition in DMF (c Z1 = M; c OH - = M; T = K). Fig. S6. Time-dependet UV-Vis spectrum changes of isatin phenylhydrazone Z1 solution after the TBA + CH 3 COO - addition in DMF (c Z1 = M; c CH3COO - = M; T = K). 13
14 Fig. S7. The time-dependent absorbance changes of isatin phenylhydrazone Z1 at 450nm and 405 nm ( M) after addition of M TBA + CH 3 COO - in DMF (c Z1 = M; c CH3COO - = M; T = K). Fig. S8. The time-dependent absorbance changes of isatin phenylhydrazone Z1 at 450nm and 405 nm ( M) after addition of M TBA + CH 3 COO - in DMF (c Z1 = M; c CH3COO - = M; T = K). 14
15 Fig. S9. 1 H NMR spectrum of Z2 in DMSO-d 6 before and after TBA + F - addition (T = K). Fig. S10. Absorbance change of Z1 + TBA + F - solution at 400nm ( -----) and 450 nm ( -----) in DMF due to 390 s photochemical initialization ( ) and 400 s back thermal relaxation ( ) (c Z1 = M; c F - = M; T = K). Half-life of photochemical transformation (t 1/2 = 43 s) increases due to the Z1 concentration increase (t 1/2 was calculated from mono-exponential fit of absorbance change at 450 nm). 15
16 Fig. S11. Reversible cycles of Z2 + TBA + F - solution absorbance at 450 nm in DMF due to photochemical initialization and back thermal relaxation (26 cycles). Fig. S12. Reversible cycles of Z1 + TBA + OH - solution absorbance at 400 and 450 nm in DMF due to photochemical initialization and back thermal relaxation at two different Z1 concentration (Figures A and B). 16
17 Fig. S13. Dependence of the photochemical A to B transformation rate constant k (s -1 ) on the light intensity in DMF (λ irr = 465 nm; c Z1 = M; c F - = M; T = K). Fig. S14. Dependence of the photochemically induced A to B form transformation conversion (absorbance difference at 450 nm in the initial and photostationary state) on the light intensity in DMF (λ irr = 465 nm; c Z1 = M; c F - = M; T = K). 17
18 MeOH addition The addition of MeOH to 1:TBA + F (or 2:TBA + F) solution mixture in DMF results in the A-form destruction (Fig. S15). The absorption band at 450 nm gradually vanishes after MeOH addition and a new hypsochromic band at approximately 385 nm appears. In the next reaction phase, the new band shifts bathochromically to 395 nm (Figs. S15 and S16). Fig. S15. The UV-Vis spectral changes of 1:TBA + F solution mixture after the addition of different MeOH concentration (solvent: DMF; c Z1 = M; c F - = M; T = K). Fig. S16. Time-dependence of the 1:TBA + F solution mixture absorbance at 470 nm at different MeOH concentration (solvent: DMF; c Z1 = M; c F - = M; T = K). 18
19 Based on the observed spectral changes, we assigned the product structure in the initial reaction phase to enol D-form (Scheme S3). Scheme S3. Gradual A-form transformation to initial Z-isomers in the presence of MeOH. Because MeOH is stronger acid compared to A-form, the thermodynamically more stable tetrabutylammonium methanolate (CH 3 O - TBA + ) is formed. The absorption band appearance with A at 385 nm in the initial reaction phase is therefore the result of azo D-form formation (Fig. S15). The D-form formation is relatively fast reaction. In the next reaction phase (at high MeOH concentration over M), the relatively slow D-form transformation back to the initial isatine phenylhydrazones Z1 and Z2 occurs and this results in the A bathochromic shift to 395 nm. The final UV-Vis and 1 H NMR spectra are almost identical with initial UV-Vis and 1 H NMR spectra spectra of 1 and 2 in MeOH (Figs. S15 and S17). The small A shift results from the increase in solution ionic strength due to the TBA + F - presence. 19
20 Fig. S17. 1 H NMR spectrum of Z1 in DMSO-d 6 before and after TBA + F - addition followed by MeOH addition (T = K). 20
21 ADDITIONAL REFERENCES [60] W.H. Press, S. Teukolsky, W. Vetterling, B. Flannery, Numerical Recipes: The Art of Scientific Computing, Cambridge University Press, New York, [61] Wolfram Research, Inc., Mathematica, Version 9.0, Champaign, IL, [62] P. Klán, J. Wirz, Spectrophotometric Determination of the Reaction Progress, in: J. Coxon, P. Bailey, L. Field, J.A. Gladysz, P. Parsons, P. Stang (Eds.), Photochemistry of Organic Compounds: From Concepts To Practice, John Wiley & Sons Ltd, 2009, Chichester, pp [63] E.S. Galbavy, K. Ram, C. Anastasio, 2-Nitrobenzaldehyde as a chemical actinometer for solution and ice photochemistry, J. Photochem. Photobiol. A Chem., 2010, 209, , [64] T. Lehóczki, É. Józsa, K. Ösz, Ferrioxalate actinometry with online spectrophotometric detection, J. Photochem. Photobiol. A Chem., 2013, 251, 63-68, 21
Photochemical & Photobiological Sciences
Photochemical & Photobiological Sciences PAPER View Article Online View Journal View Issue Published on 02 November 2017. Downloaded by Masarykova Univerzita V Brne on 07/12/2017 13:56:24. Cite this: Photochem.
More informationLight-powered autonomous and directional molecular motion of a dissipative self-assembling system
SUPPLEMENTARY INFORMATION DOI: 10.1038/NNANO.2014.260 Light-powered autonomous and directional molecular motion of a dissipative self-assembling system Giulio Ragazzon, Massimo Baroncini, Serena Silvi,
More informationSupporting Information. Shining New Light on the Spiropyran Photoswitch: A Photocage Decides between cis-trans or Spiro-Merocyanine Isomerization.
Supporting Information Shining New Light on the Spiropyran Photoswitch: A Photocage Decides between cis-trans or Spiro-Merocyanine Isomerization. Cassandra L. Fleming, Shiming Li, Morten Grøtli, and Joakim
More informationSupporting Information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 217 Electronic Supplementary Material
More informationSupramolecular Free Radicals: Near-infrared Organic Materials with Enhanced Photothermal Conversion. Supporting Information
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2015 Supramolecular Free Radicals: Near-infrared Organic Materials with Enhanced Photothermal
More informationSupporting Information to: Proton Stabilized Photochemically Reversible E/Z Isomerization of Spiropyrans
Supporting Information to: Proton Stabilized Photochemically Reversible E/Z Isomerization of Spiropyrans L. Kortekaas, a J. Chen, a D. Jacquemin, b and W. R. Browne a a Molecular Inorganic Chemistry, Stratingh
More informationSupporting Information. BODIPY-based Ratiometric Fluorescent Probe for Sensitive and Selective Sensing of Cyanide Ion
Supporting Information BODIPY-based Ratiometric Fluorescent Probe for Sensitive and Selective Sensing of Cyanide Ion Jingtuo Zhang, a Shilei Zhu, a Loredana Valenzano, a Fen-Tair Luo, b and Haiying Liu*
More informationTransformations of Oxidized Multiwalled Carbon Nanotubes Exposed to UVC (254nm) Irradiation. Supporting Information
Electronic Supplementary Material (ESI) for Environmental Science: Nano. This journal is The Royal Society of Chemistry 2014 Transformations of Oxidized Multiwalled Carbon Nanotubes Exposed to UVC (254nm)
More informationAbsorbance (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Wavelength (nm) Wavelength (nm)
Intensity (a. u.) Absorbance (a. u.) a UV UV b Wavelength (nm) Wavelength (nm) UV UV Wavelength (nm) Wavelength (nm) Supplementary Figure 1. UV-Vis absorbance spectral changes of (a) SP-Gal (left, 10 μm),
More informationInfluence of photo-isomerisation on host-guest interaction in poly(azocalix[4]arene)s
Electronic Supplementary Information Influence of photo-isomerisation on host-guest interaction in poly(azocalix[4]arene)s Szymon Wiktorowicz, Heikki Tenhu and Vladimir Aseyev *, Department of Chemistry,
More informationThe investigation of the photokinetics of a platinum organoamine complex using the Cary 50/60
The investigation of the photokinetics of a platinum organoamine complex using the Cary 50/60 Application Note Chemical Author Jeffrey J. Comerford, PhD. Agilent Technologies, Inc. Mulgrave, Victoria 3170,
More informationRational design of light-directed dynamic spheres
Electronic Supplementary Information (ESI) Rational design of light-directed dynamic spheres Yumi Okui a and Mina Han* a,b a Department of Chemistry and Department of Electronic Chemistry Tokyo Institute
More informationSupporting Information
Supporting Information Chemo-selectivity of IBX oxidation of hydroxybenzyl alcohols in the presence of Hemicucurbit[6]uril Hang Cong, a,b Takehiko Yamato* a and Zhu Tao b a Department of Applied Chemistry,
More informationTime-Programmed Helix Inversion in Phototunable Liquid Crystals
Time-Programmed Helix Inversion in Phototunable Liquid Crystals Sarah Jane Aßhoff, Supitchaya Iamsaard, Alessandro Bosco, Jeroen J. L. M.Cornelissen, Ben L. Feringa and Nathalie Katsonis* Electronic Supplementary
More informationInvestigation of Cation Binding and Sensing by new Crown Ether core substituted Naphthalene Diimide systems
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 218 Supplementary Material Investigation
More informationElectronic Supplementary Information
Electronic Supplementary Information Influence of DNA-binding on the photochromic equilibrium of a chromene derivative Sergey V. Paramonov, Vladimir Lokshin, Heiko Ihmels, Olga A. Fedorova Contents: Synthesis
More informationSupplement of A new source of methylglyoxal in the aqueous phase
Supplement of Atmos. Chem. Phys., 16, 2689 2702, 2016 http://www.atmos-chem-phys.net/16/2689/2016/ doi:10.5194/acp-16-2689-2016-supplement Author(s) 2016. CC Attribution 3.0 License. Supplement of A new
More informationStereocontrolled Self-Assembly and Photochromic Transformation of
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2018 Supporting Information for Stereocontrolled Self-Assembly and Photochromic Transformation
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationELECTRONIC SUPPLEMENTARY INFORMATION
Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences. This journal is The Royal Society of Chemistry and Owner Societies 2017 ELECTRONIC SUPPLEMENTARY INFORMATION Fabiano
More informationSupporting Informations for. 1,8-Naphthyridine-based molecular clips for off-on fluorescence sensing
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting Informations for 1,8-aphthyridine-based molecular clips for off-on fluorescence
More informationSupporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin*
Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Supporting Information Fluorescent and Colorimetric Probe Containing Oxime-Ether for Pd 2+ in Pure
More informationSupporting Information. Use of activated enol ethers in the synthesis of pyrazoles: reactions with hydrazine and a study of pyrazole tautomerism
Supporting Information for Use of activated enol ethers in the synthesis of pyrazoles: reactions with hydrazine and a study of pyrazole tautomerism Denisa Tarabová 1, Stanislava Šoralová 2,3, Martin Breza
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
More informationSupporting Information
Supporting Information In Situ Ratiometric Quantitative Tracing Intracellular Leucine Aminopeptidase Activity via an Activatable Near- Infrared Fluorescent Probe Kaizhi Gu, Yajing Liu, Zhiqian Guo,*,,#
More informationSupporting Information for. Metallonaphthalocyanines as Triplet Sensitizers for Near-Infrared. Photon Upconversion beyond 850 nm
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2015 Supporting Information for Metallonaphthalocyanines as Triplet Sensitizers for
More informationA BODIPY-based fluorescent probe for the differential
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 15 Supporting information A BODIPY-based fluorescent probe for the differential recognition of Hg(II)
More informationA dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex
Supporting Information (SI) A dual-model and on off fluorescent Al 3+ /Cu 2+ - chemosensor and the detection of F /Al 3+ with in situ prepared Al 3+ /Cu 2+ complex Xiaoya Li, Mingming Yu, Faliu Yang, Xingjiang
More informationELECTRONIC SUPPLEMENTARY INFORMATION
Multifunctional switching of a photo- and electro-chemiluminescent Iridium complex Simone Monaco, a Monica Semeraro, a Wenjuan Tan, b He Tian,* b Paola Ceroni,* a,c and Alberto Credi* a,c a Photochemical
More informationAn unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP)
This journal is The Royal Society of Chemistry 213 Supplementary Information for An unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP) Lei Shi, Ping Hu, Yanliang Ren and
More informationN-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
More informationElectronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective
Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,
More informationElectronic Supplementary Information (ESI) for. Stereoselective photoreaction in P-stereogenic dithiazolylbenzo[b]phosphole chalcogenides
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 216 Electronic Supplementary Information
More informationHighly Water-soluble BODIPY-based Fluorescent Probes for Sensitive Fluorescent Sensing of Zinc (II)
Supporting Information Highly Water-soluble BODIPY-based Fluorescent Probes for Sensitive Fluorescent Sensing of Zinc (II) Shilei Zhu, [a] Jingtuo Zhang, [a] Jagadeesh Janjanam, [a] Giri Vegesna, [a] Fen-Tair
More informationMolecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
More informationA colorimetric and fluorescent turn-on sensor for pyrophosphate. anion based on dicyanomethylene-4h-chromene framework
Electronic Supplementary Information (ESI) A colorimetric and fluorescent turn-on sensor for pyrophosphate anion based on dicyanomethylene-4h-chromene framework Xiaomei Huang, Zhiqian Guo, Weihong Zhu*,
More informationUnidirectional Photoinduced Shuttling in a Rotaxane with a Symmetric Stilbene Dumbbell
opyright WLY-V Verlag mb, -6945 Weinheim, 200. Supporting nformation for ngew. hem. nt. d. Z8537 Unidirectional Photoinduced Shuttling in a Rotaxane with a Symmetric Stilbene umbbell arol. Stanier, Sara.
More informationA fluorescent ph probe for acidic organelle in living cells
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information for A fluorescent ph probe for acidic organelle in
More informationFluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium
Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing
More information1+2 on GHD (5 µl) Volume 1+2 (µl) 1 on GHD 1+2 on GHD
1+2 on GHD (20 µl) 1+2 on GHD (15 µl) 1+2 on GHD (10 µl) 1+2 on GHD (5 µl) Volume 1+2 (µl) 1 on GHD 1+2 on GHD Supplementary Figure 1 UV-Vis measurements a. UV-Vis spectroscopy of drop-casted volume of
More information2,4-Dioxo-4-phenylbutanoic acid (1). Yield: 7.90 g, 80 %; pale yellow powder; m.p.: C, dcc** (from AcOEt/benzene); C10H8O4, FW: 192.
J. Serb. Chem. Soc. 82 (3) S158 S187 (2017) Supplementary material SUPPLEMENTARY MATERIAL TO Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids ILIJA N. CVIJETIĆ1, TATJANA Ž. VERBIĆ2*,
More informationSUPPLEMENTARY INFORMATION
This journal is The Royal Society of Chemistry and Owner Societies 214 SUPPLEMENTARY INFORMATION Photophysical Properties and Photochemistry of Substituted Cinnamates and Cinnamic Acids for UVB Blocking:
More informationCorygaline A, Hexahydrobenzophenanthridine Alkaloid with. Unusual Carbon Skeleton from Corydalis bungeana Turcz.
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information for Corygaline A, Hexahydrobenzophenanthridine Alkaloid
More informationSupporting Information:
Supporting Information: Visible Light Initiated Thiol-Michael Addition Polymerizations with Coumarin-based Photo-base Generators, Another Photoclick Reaction Strategy Xinpeng Zhang, Weixian Xi, Chen Wang,
More informationSupporting Information
Supporting Information Photo-controlled reversible guest uptake, storage and release by azobenzene-modified microporous multi-layer films of pillar[5]arenes Tomoki Ogoshi,,,,* Shu Takashima and Tada-aki
More informationSolvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More informationChap. 12 Photochemistry
Chap. 12 Photochemistry Photochemical processes Jablonski diagram 2nd singlet excited state 3rd triplet excited state 1st singlet excited state 2nd triplet excited state 1st triplet excited state Ground
More informationSUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore
SUPPORTING INFORMATION A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore Serdar Atilgan,, Tugba Ozdemir, and Engin U. Akkaya * Department
More informationSupporting Information. An AIE active Y-shaped diimidazolylbenzene: aggregation and
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information An AIE active Y-shaped diimidazolylbenzene: aggregation
More informationSupporting Information
Supporting Information Photophysical Properties of the Series fac- and mer-(-phenylisoquinolinato-n^c ) x (- phenylpyridinato-n^c ) 3-x Iridium(III) (x = to 3) Joseph C. Deaton *,, Ralph H. Young, Jerome
More informationUniversity of Groningen. Mechanisms in non-heme iron oxidation catalysis Chen, Juan
University of Groningen Mechanisms in non-heme iron oxidation catalysis Chen, Juan IMPORTNT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please
More informationCN NC. dha-7. dha-6 R' R. E-vhf (s-trans) E-vhf (s-cis) R CN. Z-vhf (s-cis) Z-vhf (s-trans) R = AcS R' = AcS
R' R R' R dha-6 dha-7 R' R R' R E-vhf (s-cis) E-vhf (s-trans) R R' R R' Z-vhf (s-cis) Z-vhf (s-trans) R = R' = Supplementary Figure 1 Nomenclature of compounds. Supplementary Figure 2 500 MHz 1 H NMR spectrum
More informationElectronic Supplementary Information. Selective detection of Al 3+ and citric acid with a fluorescent amphiphile
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Selective detection of Al 3+ and citric
More informationElectronic Supporting Information (ESI)
Electronic Supporting Information (ESI) FRET operated sensor for intracellular ph mapping: Strategically improved efficiency on moving from anthracene to naphthalene derivative Arnab Banerjee a, Animesh
More informationSelf-Assembly of Single Amino acid-pyrene Conjugates with Unique Structure-Morphology Relationship
Electronic Supplementary Material (ESI) for Soft Matter. This journal is The Royal Society of Chemistry 2017 Self-Assembly of Single Amino acid-pyrene Conjugates with Unique Structure-Morphology Relationship
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Synthesis of Functionalized Thia Analogues of Phlorins and Covalently Linked Phlorin-Porphyrin Dyads Iti Gupta a, Roland Fröhlich b and Mangalampalli Ravikanth *a a Department of
More informationA selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) A selenium-contained aggregation-induced
More informationSupporting Information. Light-induced Wide Range Color Switching of Liquid Crystal. Blue Phase doped with Hydrogen-bonded Chiral Azobenzene.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Light-induced Wide Range Color Switching of Liquid Crystal Blue Phase
More informationA Visible Near-Infrared Chemosensor for Mercury Ion
A Visible Near-Infrared Chemosensor for Mercury Ion Mei Zhu, Mingjian Yuan, Xiaofeng Liu, Jialiang Xu, Jing Lv, Changshui Huang Huibiao Liu, Yuliang Li,* Shu Wang, Daoben Zhu Beijing National Laboratory
More informationSupporting Information
Supporting Information Highly Selective Colorimetric Chemosensor for Co 2+ Debabrata Maity and T. Govindaraju* Bioorganic Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced
More informationSynthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property
Supporting Information for: Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Wen-Bin Jia, Hao-Wei Wang, Long-Mei Yang, Hong-Bo Lu, Lin Kong, Yu-Peng
More informationElectronic supplementary information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 205 Electronic supplementary information High efficiency, thermally activated, delayed fluorescence
More informationUV-Vis Absorption Experiment 5: Beer- Lambert Law and the Temperature Dependence of the Crystal Violet- Sodium Hydroxide Reaction
1 UV-Vis Absorption Experiment 5: Beer- Lambert Law and the Temperature Dependence of the Crystal Violet- Sodium Hydroxide Reaction Overview In Part A of this experiment, the absorption behaviour of crystal
More informationPhotoinduced Guest Transformation Promotes Translocation of Guest from Hydroxypropyl-β-Cyclodextrin to Cucurbit[7]uril
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Photoinduced Guest Transformation Promotes Translocation of Guest from Hydroxypropyl-β-Cyclodextrin
More informationSynthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine Hydrate in Aqueous Medium
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Synthesis of Dihydroquinoline Based Merocyanines as Naked Eye and Fluorogenic sensors for Hydrazine
More informationVishal Kachwal a, Parvej Alam a, Hare Ram Yadav b, Saleem Pasha a, Angshuman Roy Choudhury b, Inamur Rahaman Laskar *a
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Simple Ratiometric Push-Pull
More informationSupporting information. An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling
Supporting information An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling X. Shang, 1 R. Lai, 1,3 X. Song, 1 H. Li, 1,3 W. Niu, 2 and J. Guo 1 * 1. Department of Chemistry,
More informationFacile Synthesis of Flavonoid 7-O-Glycosides
Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
More informationSupporting Information
Supporting Information Unprecedented solvent-dependent sensitivities in highly efficient detection of metal ions and nitroaromatic compounds by a fluorescent Ba MOF Rongming Wang, Xiaobin Liu, Ao Huang,
More informationSupplementary Information
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2014 Supplementary Information Rational Design of Tetraphenylethylene-based Luminescent
More informationTunable Visible Light Emission of Self-Assembled Rhomboidal Metallacycles
Tunable Visible Light Emission of Self-Assembled Rhomboidal Metallacycles J. Bryant Pollock,* Gregory L. Schneider, Timothy R. Cook, Andrew S. Davies, Peter J. Stang* Department of Chemistry, University
More informationA ratiometric luminescent sensing of Ag + ion via in situ formation of coordination polymers
Electronic Supplementary Information (ESI) A ratiometric luminescent sensing of Ag + ion via in situ formation of coordination polymers Dong-Hua Li, a Jiang-Shan Shen, b Na Chen, a Yi-Bin Ruan a and Yun-Bao
More informationPART SPECTROPHOTOMETRIC STUDIES
PART SPECTROPHOTOMETRIC STUDIES CHAPTER General Principles of Spectrophotometry 123 In absorption spectroscopy, absorption measurements based upon ultraviolet light and visible radiation find application
More informationLambert s law. Beer s law. di x / I x = -kdx (-di x = k I x dx) = - a c dx. I/I 0 = e -kl T = A = - log (T) = - log (I/I 0 )
di x / I x = -kdx (-di x = k I x dx) Integrating this equation from x=0 ~ l (I x =I 0 ~I) gives ; ln I ln I 0 = -kl ln I/I 0 = -kl Expressing the number of photons absorbed by the slab as di x, and the
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) A thin-layered chromatography plate prepared from naphthalimide-based receptor immobilized SiO 2 nanoparticles as a portable chemosensor and adsorbent for Pb
More informationSynthesis, characterization and molecular recognition of bis-platinum terpyridine dimer. Supporting information
This journal is (c) The Royal Society of Chemistry 008 Synthesis, characterization and molecular recognition of bis-platinum terpyridine dimer Robert Trokowski, Shigehisa Akine, Tatsuya abeshima Graduate
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science Electronic Supplementary Information NIR Fluorescent Biotinylated Cyanine Dye: Optical Properties and Combination with
More informationSuper-Resolution Monitoring of Mitochondrial Dynamics upon. Time-Gated Photo-Triggered Release of Nitric Oxide
Supporting Information for Super-Resolution Monitoring of Mitochondrial Dynamics upon Time-Gated Photo-Triggered Release of Nitric Oxide Haihong He a, Zhiwei Ye b, Yi Xiao b, *, Wei Yang b, *, Xuhong Qian
More informationUnravelling the Photoswitching Mechanism in Donor Acceptor Stenhouse Adducts
Supporting Information Unravelling the Photoswitching Mechanism in Donor Acceptor Stenhouse Adducts Michael M. Lerch, Sander J. Wezenberg, Wiktor Szymanski,, Ben L. Feringa*, Centre for Systems Chemistry,
More informationSupporting Information for
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information for Sweet Ionic Liquid Gels: Materials for Sweetening of Fuels Floriana
More informationSupporting Information
Supporting Information Bromodimethylsulfonium bromide (BDMS) as a Potential Candidate for Photocatalytic Selective xidation of Benzylic Alcohols Using xygen and Visible Light Sarifuddin Gazi, Rajakumar
More informationSupporting Information
This journal is The Royal Society of Chemistry 212 Supporting Information Novel pyrene- and anthracene-based Schiff base derivatives as Cu 2+ and Fe 3+ fluorescence turn-on sensors and for aggregation
More informationSupporting Information
Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,
More informationSupramolecular hydrogen-bonded photodriven actuators based on an azobenzenecontaining
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2017 Supporting Information Supramolecular hydrogen-bonded photodriven actuators
More informationSupporting Information
Supporting Information Towards Singlet Oxygen Delivery at a Measured Rate: A Selfreporting Photosensitizer Sundus Erbas-Cakmak #, Engin U. Akkaya # * # UNAM-National Nanotechnology Research Center, Bilkent
More informationUV vis Spectra and Photoswitching
UV vis Spectra and Photoswitching Supplementary Figure 1 Overlay of the UV vis absorption spectra of compound 1 6 (compound 1 and 2: ~4 µm; compounds 3 6: ~20 µm; toluene; room temperature) with their
More informationDNA binding properties, histidine interaction and cytotoxicity studies. of water soluble ruthenium(ii) terpyridine complexes.
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 DNA binding properties, histidine interaction and cytotoxicity studies of water soluble
More informationUltra-Sensitive ph Control of Supramolecular Polymers and Hydrogels: pk a Matching of Biomimetic Monomers
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2014 Supplementary Information for Ultra-Sensitive ph Control of Supramolecular Polymers and
More informationSUPPLEMENTARY INFORMATION
doi:10.1038/nature14137 1. Supplementary Methods 2. Supplementary Text 2.1 Physico-Chemical Properties and Structural Elucidation of Compound 1. 2.2 Physico-Chemical Properties and Structural Elucidation
More informationZiessel a* Supporting Information (75 pages) Table of Contents. 1) General Methods S2
S1 Chemistry at Boron: Synthesis and Properties of Red to Near-IR Fluorescent Dyes based on Boron Substituted Diisoindolomethene Frameworks Gilles Ulrich, a, * Sebastien Goeb a, Antoinette De Nicola a,
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information Sulfonato-imino copper(ii) complexes : fast and general Chan-
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 pk a Modulation in Rhodamine Based Probes for Colorimetric Detection of
More informationElectronic Supplementary Informations
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Informations A radical approach for fluorescent
More informationLuminescent Terbium and Europium Probes for Lifetime Based Sensing of Temperature between 0 and 70 C
Supporting Information of Luminescent Terbium and Europium Probes for Lifetime Based Sensing of Temperature between 0 and 70 C Jiangbo Yu *a, d, e Lining Sun a, b, d, Hongshang Peng a, c, Matthias I. J.
More informationSupporting Information for. Immobilizing Tetraphenylethylene into Fused Metallacycles: Shape Effects on Fluorescence Emission
Supporting Information for Immobilizing Tetraphenylethylene into Fused Metallacycles: Shape Effects on Fluorescence Emission Zhixuan Zhou, Xuzhou Yan,,,, Manik Lal Saha,,, Mingming Zhang, Ming Wang,, Xiaopeng
More informationBiasing hydrogen bond donating host systems towards chemical
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Biasing hydrogen bond donating host systems towards chemical warfare agent
More informationSupporting Information. Application of the Curtius rearrangement to the synthesis of 1'- aminoferrocene-1-carboxylic acid derivatives
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Supporting Information Application
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the wner Societies 217 Electronic Supplementary Information Cylcodextrin-assisted Modulation in the Photophysical
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More information