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Chemical Structure| 7681-65-4 Chemical Structure| 7681-65-4
Chemical Structure| 7681-65-4

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CAS No.: 7681-65-4

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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, , 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, , 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, .

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.

Keywords: copper(I) iodide coordination polymers ; photophysics ; TADF

Purchased from AmBeed: ; ; ; ; ; ; ; ;

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.

Purchased from AmBeed: ; ; ;

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.

Purchased from AmBeed: ; ; ; ;

Alternative Products

Product Details of [ 7681-65-4 ]

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

Safety of [ 7681-65-4 ]

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

Calculated chemistry of [ 7681-65-4 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

0.0 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

None
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

None
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

None
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

None
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

None
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

None

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

None
Solubility None mg/ml ; None mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

None
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

None
Solubility None mg/ml ; None mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

None
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

None
Solubility None mg/ml ; None mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

None

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 None
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 None
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 None
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 None
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 None
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 None
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

None cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 None
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 None
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 None
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 None
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

None

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

None alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

None alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 None
 

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