How to build and race a fast nanocar Synthesis Information

Save this PDF as:
 WORD  PNG  TXT  JPG

Size: px
Start display at page:

Download "How to build and race a fast nanocar Synthesis Information"

Transcription

1 How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria Departments of Chemistry and Materials Science and NanoEngineering, and the Smalley- Curl Institute and NanoCarbon Center, Rice University, Houston, Texas 77005, United States Scheme 1. Synthesis of Dipolar Racer (1). 1

2 Experimental General synthetic methods 1 H NMR and 13 C NMR spectra were recorded at 600 and 150 MHz, respectively. Chemical shifts (δ) are reported in ppm from tetramethylsilane (TMS). All glassware was oven-dried overnight prior to use. Reagent grade tetrahydrofuran (THF) was distilled from sodium benzophenoneketyl under N 2 atmosphere. Triethylamine (Et 3 N), and dichloromethane (CH 2 Cl 2 ) were distilled from calcium hydride (CaH 2 ) under N 2 atmosphere. THF and Et 3 N were degassed with a stream of argon for 15 min before being used in the Sonogashira coupling reactions. Palladium-catalyzed reactions were carried out under argon atmosphere. All other chemicals were purchased from commercial suppliers and used without further purification. Flash column chromatography was performed using mesh silica gel from EM Science. Thin layer chromatography (TLC) was performed using glass plates precoated with silica gel 40 F mm layer thickness purchased from EM Science. Reported procedures were followed for the synthesis of compounds 3-4 (ref. S1) and 5 (ref. S2). Dipolar Racer 1. To a solution of 7 (25 mg, mmol) in THF (10 ml) was added sodium borohydride powder (NaBH4, 29 mg, 0.77 mmol) and the mixture was cooled to -5 C. Then a mixture of formaldehyde (CH2O, 0.5 ml) and sulfuric acid (H2SO4, 2.0 ml) were added dropwise maintaining the same temperature. After the addition was complete, the mixture was stirred at room temperature for 20 min. The reaction was quenched with 15 ml of an ethanol/water (1:1 v/v) mixture and the organic phase was extracted with diethyl ether (Et2O, 3 X 20 ml). The organic extract was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed in vacuo. The residue was purified by column chromatography (silica 2

3 gel, 3% EtOAc in hexanes) to provide 1 as pale yellow solid (22 mg, 85%). 1 H NMR (600 MHz, CDCl3) δ 8.08 (s, 1H), 6.75 (s, 1H), 3.10 (s, 6H), 2.00 (br s, 12H), (m, 6H), (m, 12 H). 13 C NMR (150 MHz, CDCl3) δ , , , , , , , 77.79, 76.70, 42.69, 42.63, 42.47, 36.50, 36.48, 30.82, 30.66, 28.06, HRMS (ESI) m/z calcd. for [M+H] + C32H38N2O , found Compound 6. An oven dried 10 ml screw-cap tube equipped with a stir bar was charged under argon flow with compound 4 (300 mg, 0.89 mmol), ethynyladamantane 5 (356 mg, 2.22 mmol), Pd2(dba)3 CHCl3 (92 mg, mmol), PPh3 (117 mg, 0.45 mmol), and CuI (34 mg, mmol). Freshly distilled and degassed THF (3.75 ml) and NEt 3 (1.25mL) were added, the screw-cap tube was sealed, and the reaction mixture was stirred at 70 C for 12 h. After cooling to rt, the reaction was quenched with saturated NH4Cl(aq) (20 ml) and extracted with CH2Cl2 (2 X 30 ml). The organic phase was washed with water (30 ml), dried over anhydrous MgSO4, filtered, and the filtrate was concentrated under vacuum. The crude product was purified by column chromatography (silica gel, 5-10% EtOAc in hexanes) to provide 6 as a yellow solid (331 mg, 85%). 1 H NMR (600 MHz, CDCl3) δ 8.60 (s, 1H), 8.04 (br s, 1H), 8.03 (s, 1H), 2.25 (s, 3H), (m, 3H), (m, 15 H), (m, 6H), (m, 6H). 13 C NMR (150 MHz, CDCl3) δ , , , , , , , , , 75.91, 73.14, 42.80, 42.30, 36.45, 36.26, 30.84, 30.79, 28.00, 27.90, HRMS (ESI) m/z calcd. for [M+H] + C32H36N2O3 calc , found Compound 7. In a 50 ml round-bottom flask, precursor 6 (200 mg, 0.40 mmol) was dissolved in CH2Cl2 (10 ml). Methanol (10 ml) and K2CO3 (553 mg, 4.0 mmol) were added and the mixture was stirred at room temperature for 4 h. The solvents were evaporated under vacuum and the product was purified by column chromatography (silica gel, 3% EtOAc in hexanes) to 3

4 provide 7 as a yellow solid (173 mg, 95%). 1 H NMR (600 MHz CDCl3) δ 8.06 (s, 1H), 6.73 (s, 1H), 4.66 (br s, 2H), (m, 18H), (m, 12H). 13 C NMR (150 MHz, CDCl3) δ , , , , , , , , 76.41, 73.81, 42.98, 42.46, 36.48, 36.39, 30.79, 30.67, 28.05, HRMS (ESI) m/z calcd. for [M+H] + C30H34N2O2 [M+H] , found Supplementary References S1. Tour, J. M., Rawlett, A. M., Kozaki, M., Yao, Y., Jagessar, R. C., Dirk, S. M., Price, D. W., Reed, M. A., Zhou, C.-W., Chen, J., Wang, W., Campbell, I. Synthesis and preliminary testing of molecular wires and devices. Chem. Eur. J. 7, (2001). S2. Chu, P.-L., Wang, L.-Y., Khatua, S., Kolomeisky, A. B., Link, S., Tour, J. M. Synthesis and single-molecule imaging of highly mobile adamantane-wheeled nanocars. ACS Nano 7, (2013). NMR Spectra of New Compounds: Supplementary Figure 1. 1 H NMR of 1. 4

5 Supplementary Figure C NMR of 1. Supplementary Figure 3. 1 H NMR of 6. 5

6 Supplementary Figure C NMR of 6. Supplementary Figure 5. 1 H NMR of 7. 6

7 Supplementary Figure C NMR of 7. 7

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,

More information

A TPE-oxazoline molecular switch with tunable multi-emission in. both solution and solid state

A TPE-oxazoline molecular switch with tunable multi-emission in. both solution and solid state Electronic Supplementary Information (ESI) A TPE-oxazoline molecular switch with tunable multi-emission in both solution and solid state Qingkai Qi a, Xiaofeng Fang b, Yifei Liu* b, Peng Zhou b, Yumo Zhang

More information

Supporting Information

Supporting Information Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel*

Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel* Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2Mg 2 2Li ** Stefan H. Wunderlich and Paul Knochel* Ludwig Maximilians-Universität München, Department Chemie & Biochemie

More information

Carbonylative Coupling of Allylic Acetates with. Arylboronic Acids

Carbonylative Coupling of Allylic Acetates with. Arylboronic Acids Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Carbonylative Coupling of Allylic Acetates with Arylboronic Acids Wei Ma, a Ting Yu, Dong Xue,*

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Supporting information. Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation.

Supporting information. Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation. Supporting information Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation Saithalavi Anas, Alex Cordi and Henri B. Kagan * Institut de Chimie

More information

Supplementary Information. Mapping the Transmission Function of Single-Molecule Junctions

Supplementary Information. Mapping the Transmission Function of Single-Molecule Junctions upplementary Information Mapping the Transmission Function of ingle-molecule Junctions Brian Capozzi 1, Jonathan Z. Low 2, Jianlong Xia 3, Zhen-Fei Liu 4, Jeffrey B. Neaton 5,6, Luis M. Campos 2, Latha

More information

Diastereoselectivity in the Staudinger reaction of. pentafluorosulfanylaldimines and ketimines

Diastereoselectivity in the Staudinger reaction of. pentafluorosulfanylaldimines and ketimines Supporting Information for Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines Alexander Penger, Cortney. von ahmann, Alexander S. Filatov and John T. Welch* Address:

More information

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information Palladium-Catalyzed Oxidative Allylation of Bis[(pinacolato)boryl]methane:

More information

Supporting Information

Supporting Information Intramolecular hydrogen-bonding activation in cysteines. New effective radical scavenging Luisa Haya, a Iñaki Osante, b Ana M. Mainar, a Carlos Cativiela, b Jose S. Urieta*,a a Group of Applied Thermodynamics

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany Engineering Polymeric Chiral Catalyst Using Hydrogen Bonding and Coordination Interactions Lei Shi, 1,2 Xingwang Wang, 1 Christian A. Sandoval,

More information

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0

More information

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs)

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs) Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 27 Electronic Supplementary Information bis-zn II salphen complexes bearing pyridyl functionalized

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 ph-controlled Reversible Formation of a Supramolecular Hyperbranched Polymer Showing Fluorescence Switching Bingran

More information

Electronic Supplementary Information

Electronic Supplementary Information S1 Electronic Supplementary Information Direct Aerobic Oxidation of 2-Benzylpyridines in a Gas- Liquid Continuous-Flow Regime Using Propylene Carbonate as Solvent Bartholomäus Pieber and C. Oliver Kappe*

More information

Electronic Supporting Information

Electronic Supporting Information Electronic Supporting Information Reactions of Tp(NH=CPh 2 )(PPh 3 )Ru Cl with HC CPh in the presence of H 2 O: Insertion/Hydration Products Chih-Jen Cheng, a Hung-Chun Tong, a Yih-Hsing Lo,* b Po-Yo Wang,

More information

A supramolecular approach for fabrication of photo- responsive block-controllable supramolecular polymers

A supramolecular approach for fabrication of photo- responsive block-controllable supramolecular polymers Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information A supramolecular approach for fabrication of photo- responsive

More information

Table of Contents 1. General procedure for the chiral phosphoric acid catalyzed asymmetric reductive amination using benzothiazoline

Table of Contents 1. General procedure for the chiral phosphoric acid catalyzed asymmetric reductive amination using benzothiazoline Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor Kodai Saito, Takahiko Akiyama* Department of Chemistry, Faculty of Science, Gakushuin University,

More information

Supporting Information

Supporting Information Electronic upplementary Material (EI) for Journal of Materials Chemistry B. This journal is The Royal ociety of Chemistry 216 upporting Information A dual-functional benzobisthiadiazole derivative as an

More information

Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot

Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot Laure-Emmanuelle Perret-Aebi, Alexander von Zelewsky 1, Christiane Dietrich- Buchecker and Jean-Pierre Sauvage Bis-5,6-pinene

More information

Supporting Information for Exploration of C H and N H-bond functionalization towards 1-(1,2-diarylindol-3-yl)- tetrahydroisoquinolines

Supporting Information for Exploration of C H and N H-bond functionalization towards 1-(1,2-diarylindol-3-yl)- tetrahydroisoquinolines Supporting Information for Exploration of C H and N H-bond functionalization towards 1-(1,2-diarylindol-3-yl)- tetrahydroisoquinolines Michael Ghobrial, Marko D. Mihovilovic and Michael Schnürch* Address:

More information

Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation

Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts

More information

A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media

A turn-on coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media Styliani Voutsadaki, George K. Tsikalas, Emmanuel Klontzas, George E. Froudakis, and Haralambos E.

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature24451 Chemical synthesis of USP7 compounds General 1 H, 13 C and 19 F nuclear magnetic resonance (NMR) spectra were obtained on either Bruker or Varian spectrometers at 300 or 400 MHz,

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION SUPPLEMENTARY INRMATIN doi:10.1038/nature16185 Improved Synthesis of P-CDP H H H 7 + 1 TH/DM: 9/1 K 2 C 3 / 85 o C 2 days / under N 2 45% H R R 7 P-CDP 2 n A flame dried 20 ml scintillation vial equipped

More information

1. Reagents: All commercial materials were used as received unless otherwise noted. The following solvents were obtained from a JC Meyer solvent dispe

1. Reagents: All commercial materials were used as received unless otherwise noted. The following solvents were obtained from a JC Meyer solvent dispe Supporting Information Pd-catalyzed Mono-selective ortho-c H Alkylation of N-Quinolyl Benzamides: Evidence for Stereo-retentive Coupling of Secondary Alkyl Iodides Shu-Yu Zhang, Qiong Li, Gang He, William

More information

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide

A 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 information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature22309 Chemistry All reagents and solvents were commercially available unless otherwise noted. Analytical LC-MS was carried out using a Shimadzu LCMS-2020 with UV detection monitored between

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Unmasking Representative Structures of TMP-Active Hauser and Turbo Hauser Bases Pablo García-Álvarez, David V. Graham,

More information

Supporting Information

Supporting Information Supporting Information Growth of Molecular Crystal Aggregates for Efficient Optical Waveguides Songhua Chen, Nan Chen, Yongli Yan, Taifeng Liu, Yanwen Yu, Yongjun Li, Huibiao Liu, Yongsheng Zhao and Yuliang

More information

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Supporting Information Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Hua-Jin Xu, Yi Lu, *, Marcus E. Farmer, Huai-Wei Wang, Dan Zhao, Yan-Shang Kang, Wei-Yin Sun, *, Jin-Quan Yu

More information

Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes

Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes Supporting Information for Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes Marco Blangetti, Patricia Fleming and Donal F. O Shea* Centre for Synthesis and Chemical

More information

Supplementary Material

Supplementary Material Supplementary Material Rongalite /PEG 400 as reducing system in the synthesis of new glycerol derived selenol esters using anhydrides and bis (2,2 dimethyl 1,3 dioxolanylmethyl)diselenide as substrates

More information

Supporting Information

Supporting Information Supporting Information One Pot Synthesis of 1,3- Bis(phosphinomethyl)arene PCP/PNP Pincer Ligands and Their Nickel Complexes Wei-Chun Shih and Oleg V. Ozerov* Department of Chemistry, Texas A&M University,

More information

Fluorescent probe for Lewisite Simulant

Fluorescent probe for Lewisite Simulant 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 2016 Supporting information (New

More information

Tsuji Trost N-Allylation with Allylic Acetates by Using a Cellulose Palladium Catalyst

Tsuji Trost N-Allylation with Allylic Acetates by Using a Cellulose Palladium Catalyst University of Nebraska - Lincoln DigitalCommons@University of Nebraska - Lincoln U.S. Environmental Protection Agency Papers U.S. Environmental Protection Agency 2012 Tsuji Trost N-Allylation with Allylic

More information

An insulin-sensing sugar-based fluorescent hydrogel

An insulin-sensing sugar-based fluorescent hydrogel Supplementary Information An insulin-sensing sugar-based fluorescent hydrogel Sankarprasad Bhuniya and Byeang yean Kim* ational Research Laboratory, Department of Chemistry, Division of Molecular and Life

More information

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural

More information

5.37 Introduction to Organic Synthesis Laboratory

5.37 Introduction to Organic Synthesis Laboratory MIT pencourseware http://ocw.mit.edu 5.37 Introduction to rganic Synthesis Laboratory Spring 2009 For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms. URIECA

More information

Electronic Supplementary Information. for. A New Strategy for Highly Selective Fluorescent Sensing of F - and

Electronic Supplementary Information. for. A New Strategy for Highly Selective Fluorescent Sensing of F - and Electronic Supplementary Information for A New Strategy for Highly Selective Fluorescent Sensing of F - and Zn 2+ with Dual Output Modes Yinyin Bao, Bin Liu, Fanfan Du, Jiao Tian, Hu Wang, Ruke Bai* CAS

More information

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable 1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was

More information

Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011

Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 Supporting Information Experimental General procedures The product distribution of the reaction of PCl 3 for the synthesis of chlorophosphoramidites was examined in situ by 31 P NMR and 1 H- 31 P coupled

More information

HIV anti-latency treatment mediated by macromolecular prodrugs of histone deacetylase inhibitor, panobinostat

HIV anti-latency treatment mediated by macromolecular prodrugs of histone deacetylase inhibitor, panobinostat Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 206 Supporting information HIV anti-latency treatment mediated by macromolecular prodrugs of

More information

Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+

Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei

More information

Coupling with Aryl and Heteroaryl Iodides

Coupling with Aryl and Heteroaryl Iodides Regioselective Zincation of Indazoles using TMP 2 Zn 2LiCl and egishi Cross- Coupling with Aryl and Heteroaryl Iodides Andreas Unsinn and Paul Knochel* Ludwig Maximilians-Universität München, Department

More information

Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones

Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Aurora Martínez-Muñoz, David Monge,* Eloísa Martín-Zamora, Eugenia Marqués-López, Eleuterio Álvarez, Rosario Fernández,*

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information A sensitive colorimetric and fluorescent sensor based on imidazolium-functionalized

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Content Synthesis of compounds 2a, 2b in Scheme

More information

Supplementary Information

Supplementary Information Supplementary Information J. Braz. Chem. Soc., Vol. 24, No. 9, S1-S37, 2013. Printed in Brazil - 2013 Sociedade Brasileira de Química 0103-5053 $6.00+0.00 SI Chemoenzymatic Resolution of β-azidophenylethanols

More information

Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W.

Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W. Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Data for: Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes

More information

Die Belichtungsapparatur ist in der Saalausleihe erhältlich

Die Belichtungsapparatur ist in der Saalausleihe erhältlich rganisches Praktikum CP II Wintersemester 2009/10 Versuch 27 Photooxidation von 1,5-Dihydroxynaphthalin zu Juglon, Betreuer: Literatur: Robert Lechner NP Versuch 7001 (www.oc-praktikum.de) Chemikalien:

More information

Total Synthesis of (±)-Gracilioether F

Total Synthesis of (±)-Gracilioether F Total Synthesis of (±)-Gracilioether F Xin-Yue Shen, Xiao-Shui Peng,, Henry N. C. Wong*, Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin,

More information

Influence of photo-isomerisation on host-guest interaction in poly(azocalix[4]arene)s

Influence 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 information

How does A Tiny Terminal Alkynyl End Group Drive Fully Hydrophilic. Homopolymers to Self-Assemble into Multicompartment Vesicles and

How does A Tiny Terminal Alkynyl End Group Drive Fully Hydrophilic. Homopolymers to Self-Assemble into Multicompartment Vesicles and Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 04 Electronic Supplementary Information for How does A Tiny Terminal Alkynyl End Group Drive

More information

Supporting Information. Membrane labeling and Immobilization via copper-free click chemistry

Supporting Information. Membrane labeling and Immobilization via copper-free click chemistry Supporting Information Membrane labeling and Immobilization via copper-free click chemistry Heidi E. Bostic, a Matthew D. Smith, a Andrei A. Poloukhtine, b Vladimir V. Popik, b and Michael D. Best* a [a]

More information

Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes

Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes Shanmuganathan Saravanakumar, a Markus K. Kindermann, a Joachim

More information

Supporting Information

Supporting Information Supporting Information Iridium-Catalyzed Highly Regioselective Azide-Ynamide Cycloaddition to Access 5-Amido-Fully-Substituted 1,2,3-Triazoles under Mild, Air, Aqueous and Bioorthogonal Conditions Wangze

More information

Supporting Information for. An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization

Supporting Information for. An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization Supporting Information for An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization Hang Jiang, Yu Zhang, Dushen Chen, Bo Zhou, and Yanghui Zhang * Department of Chemistry, and Shanghai Key

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z50567 Wiley-VCH 2003 69451 Weinheim, Germany Metallacarborane-Based Nanostructures: A Carbon-Wired Planar Octagon** Haijun Yao, Michal Sabat, and Russell

More information

Supporting Information

Supporting Information Supporting Information Carboxyzincation Employing Carbon Dioxide and Zinc Powder: Cobalt-Catalyzed Multicomponent Coupling Reactions with Alkynes Keisuke Nogi, Tetsuaki Fujihara,* Jun Terao and Yasushi

More information

Maksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov

Maksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov 1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv

More information

Supporting Information for. Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC motif of the pectenotoxins

Supporting Information for. Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC motif of the pectenotoxins Supporting Information for Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC motif of the pectenotoxins Georgios Vassilikogiannakis, * Ioanna Alexopoulou, Maria Tofi

More information

Anion binding vs. sulfonamide deprotonation in functionalised ureas

Anion binding vs. sulfonamide deprotonation in functionalised ureas S Anion binding vs. sulfonamide deprotonation in functionalised ureas Claudia Caltagirone, Gareth W. Bates, Philip A. Gale* and Mark E. Light Supplementary information Experimental Section General remarks:

More information

Supporting Information. for. A two step synthesis of a key unit B precursor of. cryptophycins by asymmetric hydrogenation

Supporting Information. for. A two step synthesis of a key unit B precursor of. cryptophycins by asymmetric hydrogenation Supporting Information for A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation Benedikt Sammet, Mathilde Brax and Norbert Sewald* Address: Bielefeld University,

More information

Supporting Information

Supporting Information Supporting Information Highly Selective Synthesis of Hydrosiloxanes by Au-Catalyzed Dehydrogenative Cross-Coupling Reaction of Silanols with Hydrosilanes Yasushi Satoh, Masayasu Igarashi, Kazuhiko Sato,

More information

A Closer Look at the Bromine-Lithium Exchange with

A Closer Look at the Bromine-Lithium Exchange with SUPPRTIG IFRMATI A Closer Look at the Bromine-Lithium Exchange with tert-butyllithium in an Aryl Sulfonamide Synthesis Christopher Waldmann,*, tmar Schober, Günter Haufe, and Klaus Kopka, Department of

More information

Supporting Information

Supporting Information Supporting Information Phosphane-free Suzuki Miyaura Coupling of Aryl Imidazolesulfonates with Arylboronic Acids and Potassium Aryltrifluoroborates under Aqueous Conditions José Francisco Cívicos, Mohammad

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 215 Electronic Supplementary Information Axial Chiral Aggregation-Induced Emission

More information

Electronic Supplementary Information for: agent. Adam J. Plaunt, Kasey J. Clear, and Bradley D. Smith*

Electronic Supplementary Information for: agent. Adam J. Plaunt, Kasey J. Clear, and Bradley D. Smith* Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information for: 19 F NMR indicator displacement assay using synthetic

More information

A Visible Near-Infrared Chemosensor for Mercury Ion

A 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 information

Soluble Precursor of Hexacene and its Application on Thin Film Transistor

Soluble Precursor of Hexacene and its Application on Thin Film Transistor Soluble Precursor of Hexacene and its Application on Thin Film Transistor Supplementary Information Motonori Watanabe, a Wei-Ting Su, b Kew-Yu Chen,* c Ching-Ting Chien, a Ting-Han Chao, a Yuan Jay Chang,

More information

A thermally-stable enzyme detection assay that amplifies signal autonomously in water without assistance from biological reagents

A thermally-stable enzyme detection assay that amplifies signal autonomously in water without assistance from biological reagents A thermally-stable enzyme detection assay that amplifies signal autonomously in water without assistance from biological reagents Table of Contents Kimy Yeung, Kyle M. Schmid, and Scott T. Phillips* Department

More information

Supporting Information

Supporting Information Copyright WILEY-VCH Verlag GmbH & Co. KGaA, 69469 Weinheim, Germany, 2012. Supporting Information for Macromol. Rapid Commun., DOI: 10.1002/marc.201200096 Chain-growth Polymerization of Aryl Grignards

More information

Supporting Information. Stereoselective Syntheses of Trisubstituted Olefins via Platinum Catalysis α- Silylenones with Geometrical Complementarity

Supporting Information. Stereoselective Syntheses of Trisubstituted Olefins via Platinum Catalysis α- Silylenones with Geometrical Complementarity Supporting Information Stereoselective Syntheses of Trisubstituted lefins via Platinum Catalysis α- Silylenones with Geometrical Complementarity Douglas A. Rooke and Eric M. Ferreira* Department of Chemistry,

More information

Total Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol

Total Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol . This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry Total Synthesis of Gonytolides C and G, Lachnone C, and Formal Synthesis

More information

Synthesis, characterization and molecular recognition of bis-platinum terpyridine dimer. Supporting information

Synthesis, 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 information

Cascade enzymatic cleavage of the β-o-4 linkage in a lignin model compound

Cascade enzymatic cleavage of the β-o-4 linkage in a lignin model compound Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 2015 Cascade enzymatic cleavage of the β--4 linkage in a lignin model compound

More information

Synthesis and characterization of amino-functionalized Poly(propylene carbonate)

Synthesis and characterization of amino-functionalized Poly(propylene carbonate) Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supplementary Information Synthesis and characterization of amino-functionalized Poly(propylene

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 A rare case of a dye co-crystal showing better dyeing performance Hui-Fen Qian, Yin-Ge Wang,

More information

Cis Trans Proline Isomerization Effects on Collagen Triple-Helix Stability are Limited

Cis Trans Proline Isomerization Effects on Collagen Triple-Helix Stability are Limited Cis Trans Proline Isomerization Effects on Collagen Triple-Helix Stability are Limited an Dai and Felicia A. Etzkorn* Department of Chemistry, Virginia Tech, Blacksburg, VA 24061-0212 Supporting Information.

More information

Supporting Information

Supporting Information Supporting Information for Engineering of indole-based tethered biheterocyclic alkaloid meridianin into -carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization

More information

Modified Yamaguchi Reagent : Convenient and Efficient. Esterification

Modified Yamaguchi Reagent : Convenient and Efficient. Esterification Modified Yamaguchi Reagent : Convenient and Efficient Esterification Yoshinori Okuno*, Shigeki Isomura, Akihiro Nishibayashi, Aiko Hosoi, Kei Fukuyama, Masashi Ohba, Kazuyoshi Takeda Yokohama College of

More information

Working with Hazardous Chemicals

Working with Hazardous Chemicals A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training

More information

Electronic Supporting Information

Electronic Supporting 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 2014 Electronic Supporting Information

More information

Supplementary Material

Supplementary Material Supplementary Material Preparation of symmetrical C2-C2-linked bis- and tris-6-bromoindoles by Sonogashira couplings and 5-endo-dig cyclization induced by nbu 4 NF Raúl Balderrama-Martínez-Sotomayor, Mariana

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002 Supporting Information for Angew. Chem. Int. Ed. Z19663 Wiley-VCH 2002 69451 Weinheim, Germany Selective Measurements of a itroxide-itroxide Distance of 5 nm and a itroxide-copper distance of 2.5 nm in

More information

Highly Efficient Chemoselective N-TBS Protection of Anilines under Exceptional Mild Conditions in the Eco-Friendly Solvent 2- Methyltetrahydrofuran.

Highly Efficient Chemoselective N-TBS Protection of Anilines under Exceptional Mild Conditions in the Eco-Friendly Solvent 2- Methyltetrahydrofuran. Supporting Information For Highly Efficient Chemoselective N-TBS Protection of Anilines under Exceptional Mild Conditions in the Eco-Friendly Solvent 2- Methyltetrahydrofuran. Vittorio Pace, *a,b Andrés

More information

Supplementary Information. Low volume shrinkage polymers by photo Polymerization of 1,1- Bis(ethoxycarbonyl)-2-vinylcyclopropanes

Supplementary Information. Low volume shrinkage polymers by photo Polymerization of 1,1- Bis(ethoxycarbonyl)-2-vinylcyclopropanes Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information Low volume shrinkage polymers by photo Polymerization of 1,1-

More information

Why Keep a Notebook? A. Primary source of scientific information B. Unambiguous statements of the truth

Why Keep a Notebook? A. Primary source of scientific information B. Unambiguous statements of the truth The Laboratory Notebook: Transcribed from the class-notes of S. E. Denmark I. References Writing the Laboratory Notebook H. M. Kanare, American Chemical Society; Washington D. C., 1985. Organic Chemistry

More information

Supplementary Information

Supplementary Information Supplementary Information (1) Synthesis and Characterization Figure S1. 1 H-NMR of 3 (400 MHz; CDCl3; rt). Figure S2. 13 C-NMR of 3 (100 MHz; CDCl3; rt). S2 8000 7500 7000 6500 6000 5500 5000 4500 4000

More information

Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides

Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides Ashish Thakur, Kainan Zhang, Janis Louie* SUPPORTING INFORMATION General Experimental: All reactions were conducted under an atmosphere

More information

Halogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu

Halogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu Electronic Supplementary Material (ES) for CrystEngComm. This journal is The Royal Society of Chemistry 27 Halogen bonded dimers and ribbons from the self-assembly of -halobenzophenones Patricia A. A.

More information

Absorbance (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Wavelength (nm) Wavelength (nm)

Absorbance (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 information

Supporting information

Supporting information Supporting information Access to Aminated Saturated Oxygen Heterocycles via Copper-Catalyzed Aminooxygenation of Alkenes Jian Xie, Yue-Wei Wang, Lian-Wen Qi,* and Bo Zhang* State Key Laboratory of Natural

More information

Supporting Information

Supporting Information Organocatalytic Aerobic Oxidation of Benzylic sp 3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst Zhiguang Zhang, Yuan Gao, Yuan Liu, Jianjun Li, Hexin Xie, Hao Li,*, and Wei

More information