Synthesis and optical properties of tetrapyrazinoporphyrazines containing asymmetrical alkyl chains and t-butylphenyl groups

2010 ◽  
Vol 14 (06) ◽  
pp. 531-539 ◽  
Author(s):  
Chun Keun Jang ◽  
Song Hak Kim ◽  
Jae-Yun Jaung
Keyword(s):  
Visible Spectroscopy ◽  
Monomeric Species ◽  
Alkyl Chains ◽  
H Nmr ◽  
Good Solubility ◽  
Alkyl Groups ◽  
Uv Visible ◽  
Magnesium Complexes ◽  
Band Spectra ◽  
New Compounds

Tetrapyrazinoporphyrazine magnesium complexes with four long alkyl groups and four 4-tert-butyl phenyl groups at the peripheral positions were synthesized from 2,3-dicyano-5-(4-tert-butylphenyl)-6-alkyl pyrazine derivatives using freshly prepared solutions of magnesium butoxide in n-butanol. The corresponding metal-free derivatives were obtained through treatment with p-toluenesulfonic acid. The resulting chromophores contained alkyl chains substituted at their peripheries and showed good solubility in organic solvents. The fluorescence of the tetrapyrazinoporphyrazine magnesium complexes was greatly influenced by the intermolecular aggregation. Q band spectra of the porphyrazine magnesium complexes in DMF exhibited the characteristic patterns of the monomeric species, with fluorescence maxima at 653–658 nm. These new compounds were characterized using UV-visible spectroscopy, MALDI-TOF-MS and 1H NMR spectroscopy.

Synthesis of perialkynylated tetrapyrazinoporphyrazines and its Optical Properties

2009 ◽  
Vol 2009 (5) ◽  
pp. 312-316 ◽  
Author(s):  
Chun Keun Jang ◽  
Jae Yun Jaung
Keyword(s):  
Optical Properties ◽  
Nmr Spectroscopy ◽  
Laser Desorption ◽  
Diels Alder ◽  
Visible Spectroscopy ◽  
H Nmr ◽  
Uv Visible ◽  
Tof Ms ◽  
Matrix Assisted Laser ◽  
Matrix Assisted Laser Desorption

Some phthalocyanines soluble in organic solvents have been developed by peripheral introduction of substituent groups. We report a new method for preparation of the polyphenyl-substituted dicyanopyrazines based on the [2 + 4] Diels-Alder cycloaddition of the tetraphenylcyclopentadienone to an ethynyl compound. The synthesised tetrapyrazinoporphyrazinato metal complexes were characterised by UV-visible spectroscopy, MALDI-TOF-Ms (matrix-assisted laser desorption ionisation time-of-flight mass) spectroscopy, and 1H NMR spectroscopy.

Synthesis and QCM gas-sensing properties of 3,4-dialkoxyphenyl tosylamino-substituted phthalocyanines

2020 ◽  
Vol 24 (05n07) ◽  
pp. 830-839 ◽  
Author(s):  
Mika Harbeck ◽  
Zafer Şen ◽  
Dilek D. Erbahar ◽  
Esranur Fidan Çelik ◽  
Gülay Gümüş ◽  
...  
Keyword(s):  
Metal Ion ◽  
Gas Sensing ◽  
Metal Salt ◽  
Chemical Warfare Agent ◽  
Sensing Properties ◽  
Alkyl Chains ◽  
H Nmr ◽  
Gas Sensing Properties ◽  
Ft Ir ◽  
New Compounds

Octa-substituted metallophthalocyanines [M = Ni(II), Zn(II), Co(II), and Cu(II)] carrying 3,4-dialkoxyphenyl tosylamino groups at the peripheral positions have been synthesized from 1,2-dicyano-4,5-bis[(3,4-dialkoxyphenyl-tosylamino)methyl]benzene in the presence of the corresponding anhydrous metal salt. Next to the metal ion center, the length of the alkyl chains in the dialkoxyphenyl moiety ([Formula: see text], 5, 6, and 12) was varied. In total, sixteen soluble phthalocyanines have been characterized by elemental analysis, FT-IR and [Formula: see text]H-NMR spectroscopy as well as mass spectrometry. Furthermore, the gas sensing properties of these new compounds have been studied using quartz crystal microbalance transducers. The sensing properties are described on the basis of sensor responses to nine different test analytes comprising volatile organic compounds, toxic gases, and chemical warfare agent simulants. The influence of the metal ion center and substituents on sensor selectivity and sensitivity is discussed. The compounds show good performance in the gas-sensing experiments with diverse responses to the analytes. Phthalocyanine species with pronounced selectivity for polar analytes, hydrocarbons or amines have been identified among the set of sensors with the help of multivariate data exploration methods. The results reveal that quite a high diversity in terms of selectivity is introduced through the minute variations to the phthalocyanine structure.

Synthesis and optical properties of tetrapyrazinoporphyrazine containing phenylene dendron unit as a peripheral substituent

2009 ◽  
Vol 13 (08n09) ◽  
pp. 939-948 ◽  
Author(s):  
Chun Keun Jang ◽  
Jae Yun Jaung
Keyword(s):  
Catalytic Properties ◽  
Diels Alder ◽  
Laser Desorption Ionization ◽  
Visible Spectroscopy ◽  
Ionization Time ◽  
H Nmr ◽  
Flight Mass Spectrometry ◽  
Out Of Plane ◽  
New Type ◽  
Uv Visible

A dendritic shell can create a distinct micro-environment within its core. It also has the advantage of possessing unique photochemical, photophysical, electrochemical, and catalytic properties. Polyphenylene dendrons, which are characterized by their shape-persistent structures and out-of-plane twisted phenyl components, have previously been successfully attached to various functional groups. We have recently developed a convenient method for synthesizing a new type of porphyrazine that contains both flexible (linear) and more rigid (dendritic) groups. The synthesis of this completely aromatic and dendronic structure is unique in that it is based on a [2+4] Diels-Alder cycloaddition of tetraphenylcyclopentadienone to an ethynyl compound, followed by the elimination of carbon monoxide. In this study, tetrapyrazinoporphyrazinato metal and metal-free complexes were prepared by mixing 2,3-dicyano-5-polyphenylpyrazines with magnesium in n-butanol. The synthesized tetrapyrazinoporphyrazines were characterized by UV-visible spectroscopy, MALDI-TOF-MS (matrix-assisted laser desorption/ionization time-of-flight mass) spectrometry, elemental analysis and 1 H NMR spectroscopy.

scholarly journals Preparation, Spectroscopy, Physicochemical Properties and X-ray Structure Analysis of 3,4,5-TrimethoxyN(2-hydroxybenzylidene) aniline

2009 ◽  
Vol 6 (4) ◽  
pp. 1103-1108 ◽  
Author(s):  
Kodjo Charles Guillaume ◽  
Zabri Herve ◽  
Benie Anoubile ◽  
Estienne Jacques
Keyword(s):  
Ir Spectroscopy ◽  
Physicochemical Properties ◽  
Title Compound ◽  
Electronic Spectroscopy ◽  
Visible Spectroscopy ◽  
Compound A ◽  
X Ray ◽  
H Nmr ◽  
Uv Visible ◽  
Single Crystal Analysis

3,4,5-TrimethoxyN-(salicylidene) aniline was synthesized and characterized by IR spectroscopy,1H NMR and x-ray single crystal analysis. UV-visible spectroscopy was used for physicochemical tests. X-ray data reveals that the crystalline network cohesion of this compound is essentially assured by CH/pi type hydrogen bounds. It crystallized in the orthorhombic Pbcn space group. Electronic spectroscopy shows that the title compound doesn't present photochromic property but thermochromic one. Intermolecular interactions analysis confirms for this compound a thermochromic structural predisposition.

Comparative 1HNMR and UV-Visible Studies of Polyene Polymer Epoxidations Catalyzed by Iron(III), Manganese(III) and Chromium(III) Porphyrins

1998 ◽  
Vol 02 (01) ◽  
pp. 53-60 ◽  
Author(s):  
E. M. DAVORAS ◽  
R. DIAPER ◽  
A. DERVISSI ◽  
M. J. TORNARITIS ◽  
A. G. COUTSOLELOS
Keyword(s):  
Catalytic Activity ◽  
Catalytic Reaction ◽  
Manganese Porphyrin ◽  
Visible Spectroscopy ◽  
Two Phase ◽  
H Nmr ◽  
Catalytic Epoxidation ◽  
Uv Visible ◽  
Phase Systems

The catalytic epoxidation of cis-polybutadiene was studied in two-phase systems, CH 2 CI 2/ H 2 O and PhIO (solid)/ CH 2 Cl 2, using chlorochromium(III), chloromanganese(III) and chloroiron(III) tetraphenylporphyrin complexes as catalysts. Comparison of the catalytic activity of these three catalysts showed that the manganese porphyrin is the most suitable catalyst for this reaction. The results are based on reaction product ratios as determined by 1 H NMR . UV-Visible spectroscopy allowed monitoring of the metalloporphyrin evolution during the catalytic reaction.

scholarly journals Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

2017 ◽  
Vol 13 ◽  
pp. 1542-1550 ◽  
Author(s):  
Alexis Perry ◽  
Christina J Kousseff
Keyword(s):  
Metal Binding ◽  
Metal Cations ◽  
Efficient Synthesis ◽  
Visible Spectroscopy ◽  
Binding Properties ◽  
Systematic Analysis ◽  
H Nmr ◽  
Common Structure ◽  
Photoactive Materials ◽  
Uv Visible

Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using 1H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M2+ binding affinity correlated with increased alkycarboxylate tether length.

The fate of phosphorus in the bleaching of spruce TMP with the new bleaching agent – THPS

Holzforschung ◽  
2008 ◽  
Vol 62 (4) ◽  
Author(s):  
Thomas Q. Hu ◽  
Eric Yu ◽  
Brian R. James ◽  
Paolo Marcazzan
Keyword(s):  
Pulp Mill ◽  
Bleaching Agent ◽  
Visible Spectroscopy ◽  
Nmr Studies ◽  
H Nmr ◽  
Bleached Pulp ◽  
P Content ◽  
Covalently Bonded ◽  
Bonding Hypothesis ◽  
Uv Visible

Abstract Tetrakis(hydroxymethyl)phosphonium sulfate (THPS) is a newly discovered, phosphorus-based bleaching agent that has been successfully tested in a pulp mill trial. The fate of phosphorus (P) and the chemistry in the course of THPS bleaching of a spruce TMP have been studied. The amount of P introduced into the THPS-bleached pulp depends on THPS dose and the bleaching conditions and it correlates well with the brightness gain. The P introduced into THPS-bleached pulp is covalently bonded to the pulp. The THPS-bleached and tetraethylphosphonium chloride-treated pulps have been additionally treated with calcium chloride before P analysis, and the results of these experiments support the covalent bonding hypothesis. Bleaching with 0.1 and 3.0% THPS (% based on oven-dried pulp) at 60 and 110°C leads to pulps with 0.13 and 2.17 mg P g-1 pulp, respectively, which corresponds to 0.08 and 1.4% THPS. More precisely, P is covalently bonded to lignin chromophores, such as lignin coniferaldehydes. This was found by P-content analysis, UV-visible spectroscopy, and 31P{1H} NMR studies of a crude milled wood lignin (crude MWL) and a partially purified MWL isolated from a THPS-bleached pulp.

scholarly journals Refinement of Structural Leads for Centrally Acting Oxime Reactivators of Phosphylated Cholinesterases

2012 ◽  
Vol 287 (15) ◽  
pp. 11798-11809 ◽  
Author(s):  
Zoran Radić ◽  
Rakesh K. Sit ◽  
Zrinka Kovarik ◽  
Suzana Berend ◽  
Edzna Garcia ◽  
...  
Keyword(s):  
Ph Dependence ◽  
Pharmacokinetic Studies ◽  
Visible Spectroscopy ◽  
H Nmr ◽  
Pharmacokinetic Properties ◽  
Uv Visible ◽  
Cns Penetration ◽  
Intrinsic Reactivity ◽  
Hydrolysis Of

We present a systematic structural optimization of uncharged but ionizable N-substituted 2-hydroxyiminoacetamido alkylamine reactivators of phosphylated human acetylcholinesterase (hAChE) intended to catalyze the hydrolysis of organophosphate (OP)-inhibited hAChE in the CNS. Starting with the initial lead oxime RS41A identified in our earlier study and extending to the azepine analog RS194B, reactivation rates for OP-hAChE conjugates formed by sarin, cyclosarin, VX, paraoxon, and tabun are enhanced severalfold in vitro. To analyze the mechanism of intrinsic reactivation of the OP-AChE conjugate and penetration of the blood-brain barrier, the pH dependence of the oxime and amine ionizing groups of the compounds and their nucleophilic potential were examined by UV-visible spectroscopy, 1H NMR, and oximolysis rates for acetylthiocholine and phosphoester hydrolysis. Oximolysis rates were compared in solution and on AChE conjugates and analyzed in terms of the ionization states for reactivation of the OP-conjugated AChE. In addition, toxicity and pharmacokinetic studies in mice show significantly improved CNS penetration and retention for RS194B when compared with RS41A. The enhanced intrinsic reactivity against the OP-AChE target combined with favorable pharmacokinetic properties resulted in great improvement of antidotal properties of RS194B compared with RS41A and the standard peripherally active oxime, 2-pyridinealdoxime methiodide. Improvement was particularly noticeable when pretreatment of mice with RS194B before OP exposure was combined with RS194B reactivation therapy after the OP insult.

Synthesis of PAA-PAMPS-PNaSS Terpolymers as Ultraviolet-Tagged Scale Inhibitor for Industrial Water Cooling System

2017 ◽  
Vol 757 ◽  
pp. 68-72 ◽  
Author(s):  
Parinya Jitreewas ◽  
Suwicha Saengvattanarat ◽  
Phanita Tansiri ◽  
Siriporn Pranee ◽  
Sunanta Chuayprakong ◽  
...  
Keyword(s):  
Acrylic Acid ◽  
Cooling System ◽  
Water Cooling ◽  
Visible Spectroscopy ◽  
Circulating Water ◽  
H Nmr ◽  
Sodium Styrene Sulfonate ◽  
Scale Inhibition ◽  
Uv Visible ◽  
Poly Acrylic Acid

Carboxylated polymer can be used as an anti-scaling agent in circulating water cooling systems. Poly(acrylic acid) and homopolymer have some drawbacks such as slight solubility in water and low calcium tolerance leading difficulty to determine the remaining quantity of polymer in water. This research is mainly focused on synthesis and ability of poly(acrylic acid-co-2-acrylamido-2-methylpropane sulfonic acid) (PAA-PAMPS) for scale inhibition. These terpolymers varied in mole ratios of monomers were prepared via solution polymerization. The obtained polymers are then characterized by FT-IR, 1H-NMR, TGA, turbidity, and UV-visible spectroscopy. For a scale inhibition test, GB/T 16632-2008 standard is applied. The scale inhibition efficiency for 100% was found in PAA-PAMPS copolymer (7:3). Afterwards this polymer was chosen for synthesizing an ultraviolet-tagged PAA-PAMPS-PNaSS terpolymer. UV-visible spectroscopy was used to monitor benzene sulfonate structure in sodium styrene sulfonate of the polymer chain at 224 nm.

Synthesis of aromatic polyimide bearing long alkyl chains through click reaction

e-Polymers ◽  
2012 ◽  
Vol 12 (1) ◽  
Author(s):  
Hisatoyo Morinaga ◽  
Masamine Imahashi ◽  
Tsutomu Takeichi
Keyword(s):  
Molecular Weight ◽  
Spectroscopic Analysis ◽  
Click Reaction ◽  
Differential Scanning Calorimetry Analysis ◽  
Scanning Calorimetry ◽  
Aromatic Polyimide ◽  
Alkyl Chains ◽  
H Nmr ◽  
Alkyl Groups ◽  
Lower Glass Transition Temperature

AbstractA click reaction of aromatic polyimide having azide groups at both chainends (2), which was obtained by an azidation of polyimide having chloromethyl groups (1), was conducted with 1-octyne, leading to the polyimide having n-hexyl groups (3). 1H NMR spectroscopic analysis for 3 reveals that the n-hexyl groups were successfully introduced into the both chain-ends of aromatic polyimide and that a number-averaged molecular weight of the resulting polymer 3 was 6000. Differential scanning calorimetry analysis for 3 exhibited 30 °C lower glass transition temperature compared to that of 1, by introducing long alkyl groups into the aromatic polyimide chain.

Sign in / Sign up

Export Citation Format

Share Document