Structure of Copper(I)iodide
CAS No.: 7681-65-4
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Cy5 Dye Cassettes Exhibit Through-Bond Energy Transfer and Enable Ratiometric Fluorescence Sensing
Zhumin Zhang ; Jordan L. Chasteen ; Bradley D. Smith ;
Abstract: The chemosensor literature contains many reports of fluorescence sensing using polyaromatic hydrocarbon fluorophores such as pyrene, tetraphenylethylene, or polyaryl(ethynylene), where the fluorophore is excited with ultraviolet light (<400 nm) and emits in the visible region of 400–500 nm. There is a need for general methods that convert these “turn-on” hydrocarbon fluorescent sensors into ratiometric sensing paradigms. One simple strategy is to mix the responsive hydrocarbon sensor with a second non-responsive dye that is excited by ultraviolet light but emits at a distinctly longer wavelength and thus acts as a reference signal. Five new cyanine dye cassettes were created by covalently attaching a pyrene, tetraphenylethylene, or biphenyl(ethynylene) component as the ultraviolet-absorbing energy donor directly to the pentamethine chain of a deep-red cyanine (Cy5) energy acceptor. Fluorescence emission studies showed that these Cy5-cassettes exhibited large pseudo-Stokes shifts and high through-bond energy transfer efficiencies upon excitation with ultraviolet light. Practical potential was demonstrated with two examples of ratiometric fluorescence sensing using a single ultraviolet excitation wavelength. One example mixed a Cy5-cassette with a pyrene-based fluorescent indicator that responded to changes in Cu2+ concentration, and the other example mixed a Cy5-cassette with the fluorescent pH sensing dye, pyranine.
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Purchased from AmBeed: 1227040-87-0 ; 54136-26-4 ; 1195975-05-3 ; 534-17-8 ; 29079-00-3 ; 13965-03-2 ; 3375-31-3 ; 7681-65-4 ; 63149-24-6 ; 64285-36-5
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Boivin, Leo ; Schlachter, Adrien ; Fortin, Daniel ; Lescop, Christophe ; Harvey, Pierre D. ;
Abstract: The prediction of the metal cluster within a coordination polymer or complex, as well as the dimensionality of the resulting polymer or complex (i.e., 0D, 1D, 2D, or 3D), is often challenging. This is the case for Ph2P(CH2)mPPh2 ligands (1 ≤ m ≤ 8) and CuX salts, particularly for X = I. This work endeavors a systematic statistical anal. combining studies in the literature and new data, mapping the nature of the resulting CuI aggregates with eight different diphoshphines in 2:1, 3:2, 1:1, 2:3, and 1:2 CuI:Ph2P(CH2)mPPh2 molar ratios as a function of m, which lead to either pure products or mixtures Several trends are made relating stoichiometry and chain length to the CuI cluster formed (i.e., globular vs. quasi-planar). Four new X-ray structures were determined: [Cu3I2(L1)3]I, Cu3I3(L2)2, Cu2I2(L6)2, and Cu4I4(L8)2, where m is, resp., 1, 2, 6, and 8, in which the CuxIy central aggregates adopt triangular bipyramid, diamond, rhomboid, and cubane shaped motifs, resp. Photophys. measurements assisted the establishment of trends considering the paucity of the crystallog. structures. During this study, it was also found that the 0D-complex Cu2I2(Ph2P(CH2)5PPh2)2 exhibits thermally activated delayed fluorescence.
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Keywords: copper(I) iodide coordination polymers ; photophysics ; TADF
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Purchased from AmBeed: 1663-45-2 ; 7688-25-7 ; 2071-20-7 ; 27721-02-4 ; 19845-69-3 ; 6737-42-4 ; 4549-31-9 ; 7681-65-4 ; 41625-30-3
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Shao-Xiong Lennon Luo ;
Abstract: This thesis highlights strategies for fiinctionalizing carbon nanomaterials with reactive metaspecies for applications in chemical sensing and electrocatalysis. In Chapter 1, we begin with anintroduction of chemiresistive sensing using functionalized carbon nanotubes (CNTs). Thisintroduction summarizes the design, fabrication, characterization, and evaluation of carbonnanotube-based chemiresistive sensors. Potential strategies for optimizing sensitivity andselectivity are also discussed. Typical applications of'CNT-based chemiresistive sensing are alsosurveyed. In Chapter 2, we report the synthesis of Pentiptycene Polymer/Single-Walled CarbonNanotube Complexes and their applications in the selective detection of benzene, toluene, and o.xylene using chemiresistive and quartz crystal microbalance-based methods. In Chapter 3. wereport a method to efiectively immobilize transition metal selectors in close proximity to theS WCN'T surface using pentiptycene polymers containing metal-chelating backbone structures. Wehave identified sensitive, selective, and robust copper-based chemiresistive ammonia sensorsdisplaying low parts per billion detection limits. We have added these hybrid materials into theresonant radio firequency circuits of commercial near-field communication (NFC) tags to achievewireless detection ofammonia at physiologically relevant levels, offering a non-invasive and cost.efiective approach for early detection and monitoring of chronic kidney diseases. In Chapter 4we report that iptycene-containing poly(arylene ether)s (PAEs) show to limit the palladiumnanoparticles (Pd NPs) growth and stabilize the Pd NPs dispersion. SWCNT-based chemiresistorsand graphene field-efect transistors (GFETs)using these PAE-supported small Pd NPs aresensitive, selective, and robust sensory materials for hydrogen gas under ambient conditions. InChapter 5, we describe chemiresistors based on SWCNTs containing small and highly reactivecopper-based nanoparticles in sulfonated pentiptycene poly(arylene ether)s (PAEs). The sensorsshow exceptional sensitivity to trace hydrogen sulfide in wet air with a low-ppb detection limithigh selectivity over a wide range of interferants, and month-long stability under ambientconditions. In Chapter 6, we report a SWCNT-based chemiresistor catalyst combination that candetect ppb levels of' ethylene in air, driven by the chemoselectivity ofthe catalytic transformationThe utility of this ethylene sensor is demonstrated in the monitoring of senescence in red carnationsand purple lisianthus flowers.In Chapter 7, we report SWCNT-based chemiresistive sensorsbased on a catalytic system comprising a copper complex and TEMPO cocatalyst, enabling thesensitive, selective, and robust detection of trace ethanol in air. In Chapter 8, we report thesynthesis of carbon-nanomaterial-based metal chelates that enable effective electronic coupling toelectrocatalytic transition metals. The defined ligands on the graphene surfaces enable theformation of structurally precise heterogeneous molecular catalysts. We demonstrate that thedensely functionalized metal-chelated carbon nanomaterials are eliective heterogeneous catalystsin the oxygen evolution reaction with low overpotentials and tunable catalytic activity.
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DEVELOPMENT OF NOVEL RADICAL ION REACTIVITY USING ORGANIC PHOTOREDOX CATALYSIS
Chapel Hill ;
Abstract: Photoredox catalysis has traditionally been accomplished by using ruthenium or iridium polypyridyl complexes. These complexes, while robust in their application, can prove to be quite cost prohibitive. Additionally, their respective redox windows are relatively narrow, limiting the scope of substrates with which they can undergo photoinduced electron transfer. Visible light absorbing organic chromophores have proven to be cost effective alternatives to precious transition metal photoredox catalysts. Additionally, the excited state redox potentials of organic photoredox catalysts can be significantly greater than that of their inorganic counterparts allowing for the development of new methodologies on substrates that could not otherwise undergo photoinduced electron transfer. In particular, organic acridinium dyes possess photophysical properties that make them extremely potent excited state oxidants. More recently it has been demonstrated that the acridine radical in the excited state possesses and excited state oxidation potential comparable to that of dissolving metal reductants making it an excellent excited state reductant. Herein, we describe methods developed that leverage the 5.51 V of redox potential that acridinium complexes can access. Nucleophilic aromatic substitution (SNAr) is a common method for arene functionalization; however, reactions of this type are typically limited to electron-deficient aromatic halides. Herein, we describe a mild, metal_x005f_x0002_free, cation-radical accelerated nucleophilic aromatic substitution (CRA-SNAr) using a potent acridinium photoredox catalyst as an excited state oxidant. Selective substitution of arene C−O bonds on a wide array of aryl ether substrates was shown with a variety of primary amine nucleophiles. Mechanistic evidence is also presented that supports the proposed CRA-SNAr pathway. Ketone–olefin coupling reactions are common methods for the formation of carbon–carbon bonds. This reaction class typically requires stoichiometric or super stoichiometric quantities of metal reductants and catalytic variations are limited in application. Photoredox catalysis has offered an alternative method towards ketone–olefin coupling reactions, although most methods are limited in scope to easily reducible aromatic carbonyl compounds. Herein, we describe a mild, metal-free ketone–olefin coupling reaction using an excited state acridine radical super reductant as a photoredox catalyst. We demonstrate both intra and intermolecular ketone–olefin couplings of aliphatic and aromatic ketones and aldehydes. Mechanistic evidence is also presented supporting an “olefin first”ketone–olefin coupling mechanism.
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CAS No. : | 7681-65-4 |
Formula : | CuI |
M.W : | 190.45 |
SMILES Code : | [Cu+].[I-] |
MDL No. : | MFCD00010978 |
InChI Key : | LSXDOTMGLUJQCM-UHFFFAOYSA-M |
Pubchem ID : | 6432705 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H315-H317-H318-H335-H410 |
Precautionary Statements: | P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 2 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | None |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | None |
Num. H-bond donors | None |
Molar Refractivity | 14.02 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
None |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
None |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
None |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
None |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
None |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
None |
Log S (ESOL):? ESOL: Topological method implemented from |
None |
Solubility | None mg/ml ; None mol/l |
Class? Solubility class: Log S scale |
None |
Log S (Ali)? Ali: Topological method implemented from |
None |
Solubility | None mg/ml ; None mol/l |
Class? Solubility class: Log S scale |
None |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
None |
Solubility | None mg/ml ; None mol/l |
Class? Solubility class: Log S scale |
None |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
None |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
None |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
None |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
None |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
None |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
None |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
None |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
None |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
None cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
None |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
None |
Egan? Egan (Pharmacia) filter: implemented from |
None |
Muegge? Muegge (Bayer) filter: implemented from |
None |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
None |
PAINS? Pan Assay Interference Structures: implemented from |
None alert |
Brenk? Structural Alert: implemented from |
None alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
None |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In dichloromethane; | e 3-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine A solution of <strong>[445491-71-4]3-bromo-5-methanesulfonyl-pyridine</strong> (1.00 g, 4.20 mmol), 3,3,3-triethoxypropyne (1.75 g, 9.4 mmol), dichlorobis(triphenylphospine)palladium(II) (0.15 g, 0.21 mmol), copper(I)iodide (0.08 g, 0.42 mmol), triethylamine (1.80 mL, 12.7 mmol) and dichloromethane (40 mL) was heated at reflux for 48 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (1.2 g, 87% yield) as yellow solid. 1H NMR (CDCl3) delta9.08(d, 1H, J=2.4 Hz), 8.91 (d, 1H J=2.0), 8.28 (t, 1H, J=2.0 Hz), 3.75 (q, 6H, J=7.2), 3.13 (s, 3H), 1.29 (t, 9H, J=7.2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Pd(PPh3)2Cl2; In triethylamine; | Step D 5-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-pent-4-ynoic acid butyl ester (4-5) A suspension of 4-4 (0.113 g, 0.431 mmol) and n-butyl 4-pentynoate (0.0731 g, 0.474 mmol) in triethylamine (3.0 mL) was purged with Ar, then cooled to 0 C. Copper iodide (0.0021 g, 0.0108 mmol) and Pd(PPh3)2Cl2 (0.0076 g, 0.0108 mmol) were added, the ice bath was removed after ten minutes, and the resulting suspension was stirred overnight. The mixture was then partitioned between EtOAc and saturated NaHCO3 solution. The organic phase was washed with sat. NaHCO3 solution, water, and brine, then dried with MgSO4 and concentrated. Flash chromatography (silica, 45% EtOAc-Hexanes) yielded a clear, yellowish oil. 1H-NMR (CDCl3): delta 6.88 (d, J=7.9 Hz, 1 H), delta 6.69 (d, J=8.0 Hz, 1 H), delta 5.07 (br s, 1 H), delta 4.22 (t, J=4.4, 2 H), delta 4.10 (t, J=6.7 Hz, 2 H), delta 3.54 (m, 2 H), delta 2.70 (m, 2 H), delta 2.61 (m, 2 H), delta 1.61 (m, 2 H), delta 1.38 (m, 2 H), delta 0.92 (t, J=7.4 Hz, 3 H). MS (M++H) 289.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; | 2,6-Di-tert-butyl-4-trimethylsilanylethynyl-phenol: (Intermediate 167) Following General Procedure D and using 4-bromo-2,6-di-t-butyl-phenol (1.43 g, 5 mmol), triethyl amine (15 mL), anhydrous tetrahydrofuran (15 mL), copper(I)iodide (0.06 g, 0.31 mmol), trimethylsilyl acetylene (4.9 g, 50 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.18 g, 0.26 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as eluent, the title compound was obtained (1.35 g, 90percent). 1H NMR (300 MHz, CDCl3): delta7.29 (s, 2H), 5.35 (s, 1H), 1.42 (s, 18H), 0.24 (s, 9H). | |
With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; | 2,6-Di-tert-butyl-4-trimethylsilanylethynyl-phenol: (Intermediate 167) Following General Procedure D and using 4-bromo-2,6-di-t-butyl-phenol (1.43 g, 5 mmol), triethyl amine (15 mL), anhydrous tetrahydrofuran (15 mL), copper(I)iodide (0.06 g, 0.31 mmol), trimethylsilyl acetylene (4.9 g, 50 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.18 g, 0.26 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as eluent, the title compound was obtained (1.35 g, 90percent). 1H NMR (300 MHz, CDCl3): delta 7.29 (s, 2H), 5.35 (s, 1H), 1.42 (s, 18H), 0.24 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; dimethyl sulfoxide; | a) (1-Methylethylsulfonyl)phenylacetonitrile A mixture of iodobenzene (13.9g, 68mmol), <strong>[120069-21-8](1-methylethylsulfonyl)acetonitrile</strong> (20.0g, 136mmol), copper (I)iodide (1.29g, 6.8mmol) and potassium carbonate (37.6g, 272mmol) in dimethylsulfoxide (100mL) was stirred at 120 C under an atmosphere of nitrogen for 40h. The dark blue mixture was allowed to cool to room temperature, poured into 2M hydrochloric acid (300mL) and extracted with ether (200mL) and ethyl acetate (2 x 150mL). The combined organic extracts were washed with water (8 x 125mL), dried (MgSO4), filtered and evaporated in vacuoto yield a black oil. This was dissolved in dichloromethane and filtered through a large pad of 'flash' silica, eluding with dichloromethane. Fractions containing the product were combined and concentrated, yielding a yellow oil. This was distilled in a short-path distillation apparatus, providing a yellow oil (B.Pt. 230 C at 0.3 mBar). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; dimethyl sulfoxide; | PREPARATION 18 Preparation of (propane-2-sulfonyl)phenylacetonitrile A mixture of iodobenzene (13.9g, 68mmol), propane-2-sulfonylacetonitrile (20.0g, 18mmol), copper (I) iodide (1.29g, 6.8mmol) and potassium carbonate (37.6g, 272mmol) in DMSO (100mL) was stirred at 120 C under an atmosphere of nitrogen for forty hours. The dark blue mixture was allowed to cool to room temperature, poured into dilute hydrochloric acid (300mL) and extracted with ether (200mL) and ethyl acetate (2 x 150mL). The combined organic extracts were washed with water (8 x 125mL), dried (MgSO4), filtered and evaporated in vacuoto yield a black oil (20g). This was dissolved in dichloromethane and filtered through a large pad of 'flash' silica, eluding with dichloromethane. Fractions containing the product were combined and concentrated, yielding a yellow oil. This was distilled in a short-path distillation apparatus, providing a yellow oil (B.Pt. 230 C at 0.3 mBar). Also prepared in this fashion starting from methanesulfonylacetonitrile was methanesulfonyl phenylacetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; triphenylphosphine; In dichloromethane; | EXAMPLE 5 Preparation of 4-chloro-5-phenylethynylpyrimidine A mixture of 2.1 g of <strong>[63558-65-6]4-chloro-5-iodopyrimidine</strong>, 10 mL of triethylamine, 1.2 mL phenylacetylene, 80 mg copper iodide and 160 mg of dichlorobis(triphenylphosphine was stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane and evaporated in vacuo. The residue was redissolved in a few mL of dichloromethane, 10 mL of triethylamine added and the mixture heated at reflux for one hour. The heterogeneous mixture was evaporated in vacuo and the residue obtained was partitioned between water and dichloromethane. A gelatinous precipitate which formed on shaking the two layers was filtered off, enabling separation of the two layers. The organic extracts were dried over sodium sulfate, filtrated and evaporated in vacuo to yield 2.5 g of a dark brown syrup. The syrup was purified by column chromatography on silica gel, twice, eluding with hexanes, 1:1 hexanes/dichloromethane, dichloromethane and finally ethyl acetate. Like fractions from dichloromethane elution were pooled, obtaining 350 mg of the product, 5-phenylethynyl-4-chloropyrimidine as an oil which solidified to white rosettes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In dichloromethane; | EXAMPLE 3 Preparation of 4-chloro-5-(4-chlorophenylethynyl)pyrimidine A mixture of 0.6 g of 1-chloro-4-ethynylbenzene, 1.44 g of <strong>[63558-65-6]4-chloro-5-iodopyrimidine</strong> (J. Chem. Soc. Perkins Trans. I, 1977,621, Allen et al), 7.0 cc of triethylamine, 58 mg of copper iodide and 108 mg of dichlorobis(triphenylphosphine)palladium II was stirred at room temperature under nitrogen for 18 hours. The reaction mixture was evaporated in vacuo. The resulting tan solid was partitioned between water and dichloromethane and the organic extracts washed twice with water, dried over sodium sulfate and evaporated to give a dark brown solid, 1.57 g. The solid was redissolved in dichloromethane and hexanes added to give 120 mg of a beige powder after filtration. The filtrate was purified by column chromatography on silica gel using 1:1 ethyl acetate/dichloromethane as the eluant. The middle rf spot fractions (silica gel TLC in 1:1) were pooled and evaporated to give 0.8 g of a yellow solid, 4-chloro-5-(4-chlorophenylethynyl)-pyrimidine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
640 mg | Preparation of Intermediate 7-Iodo-3,4-dihydro-2H-isoquinolin-1-one (I-32b) NaNO2 (340 mg, 4.9382 mmol) was added to a solution of <strong>[66491-03-0]7-amino-3,4-dihydro-2H-isoquinolin-1-one</strong> (I-32a: 800 mg, 4.9382 mmol) in concentrated HCl (2 mL) and water (2 mL) at 0 C. The reaction mixture was stirred at 0 C. for 15 minutes. The resulting diazonium salt solution was added portion wise to a vigorously stirred biphasic mixture of DCM (25 mL), potassium iodide (4.9 g, 29.6242 mmol), copper iodide (47 mg, 0.25 mmol) and water (8 mL). The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was diluted with DCM. The organic layer was washed with 10% Na2S2SO3 solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 640 mg of the product (44.50% yield). 1H NMR (300 MHz, CDCl3): delta 8.53-8.31 (m, 1H), 7.80-7.70 (m, 1H), 7.0 (d, 1H), 6.40-6.25 (bs, 1H), 3.70-3.51 (m, 2H), 3.0 (t, 2H) LCMS: 100%, m/z=274.0 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In dichloromethane; for 2h;Inert atmosphere; | [CuI(PPh3) (L)] (1), L=4,4?-dimethoxy-2,2?-bipyridine). To achieve the synthesis of 1, CuI (1 mmol, 98percent from Sigma-Aldrich) was dissolved in dichloromethane (DCM, 10 mL) with magnetic stirring under a nitrogen atmosphere until complete dissolution of the CuI. Immediately after dissolution, the ligands 4,4?-dimethoxy-2,2?-bipyridine(L) (1 mmol, 97percent from Sigma-Aldrich) and triphenylphosphine(PPh3, 1 mmol, 99percent from Sigma-Aldrich) were added and the mixture was stirred under flowing nitrogen for 2 h in the dark. After this, the resulting orange precipitate was collected by filtration and dried under constant flow of N2 for 48 h. The yield was 75percent. 1H NMR spectrum(500 MHz, CD3COCD3) delta ppm 4.02 (s, 6H) 7.30?7.37 (m, 6H)7.38?7.43 (m, 3H) 7.44?7.50 (t, 6H) 7.52?7.57 (m, 2H) 7.60?7.65 (m,2H) 7.67?7.72 (m, 2H). IR (ATR): nu=493 (m), 503 (m), 523 (vs), 540(w), 574 (vw), 590 (vw), 694 (vs), 722 (w), 747 (m), 820 (w), 830 (w),845 (vw), 863 (w), 881 (vw), 900 (vw), 914 (vw), 998 (vw), 1023 (s),1044 (w), 1091 (vw), 1120 (vw), 1157 (vw), 1180 (vw), 1215 (m),1248 (m), 1270 (w), 1308 (w), 1325 (w), 1409 (w), 1422 (w), 1431(w), 1454 (vw), 1467 (vw), 1478 (vw), 1490 (w), 1560 (m), 1604 (m),2833 (vw), 2941 (vw), 2973 (vw), 2994 (vw), 3022 (vw), 3050 (vw),3068 (vw). Anal. for C30H27CuIN2O2P (668.94): C 53.78, H 4.21, N4.18; found C 53.13, H 4.19, N 4.15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol;Irradiation; | The method for preparing a chiral copper-iodine complex in this embodiment is as follows: a) In a 15ml centrifuge tube, add 10ml of absolute ethanol, 0.38mg of CuI, and 300ul of (S) -2- (aminomethyl) -1-ethylpyrrolidine ((S) -2- (Aminomethyl) -1 -ethylpyrrolidine), tighten the cap of the centrifuge tube.b) Shake until the raw materials of the two are mixed uniformly, and a yellow-green phosphor can be generated by irradiating with a 254nm ultraviolet lamp.c) The raw material solution was left to stand overnight, and colorless transparent crystals were found. Decant the ethanol in the centrifuge tube and wash the crystals with n-hexane to obtain a chiral copper-iodine complex crystal with a clean surface.d) Through single crystal X-ray characterization and OLEX software data analysis, the structure information of the chiral copper-iodine complex crystal is obtained, so as to obtain the coordination mode and two-core structure between copper iodine and chiral organic molecules, and the chemical formula is ((( S) -2- (Aminomethyl) -1-ethylpyrrolidine)) 2Cu2I2 |