Home Other Building Blocks Tris(2-pyridylmethyl)amine

Tris(2-pyridylmethyl)amine

CAS No.:
16858-01-8
Catalog Number:
AG001Y5H
Molecular Formula:
C18H18N4
Molecular Weight:
290.3623
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%
In Stock USA
United States
$82
- +
5g
98%
In Stock USA
United States
$250
- +
10g
98%
In Stock USA
United States
$413
- +
25g
98%
In Stock USA
United States
$825
- +
Product Description
Catalog Number:
AG001Y5H
Chemical Name:
Tris(2-pyridylmethyl)amine
CAS Number:
16858-01-8
Molecular Formula:
C18H18N4
Molecular Weight:
290.3623
MDL Number:
MFCD14708176
IUPAC Name:
1-pyridin-2-yl-N,N-bis(pyridin-2-ylmethyl)methanamine
InChI:
InChI=1S/C18H18N4/c1-4-10-19-16(7-1)13-22(14-17-8-2-5-11-20-17)15-18-9-3-6-12-21-18/h1-12H,13-15H2
InChI Key:
VGUWFGWZSVLROP-UHFFFAOYSA-N
SMILES:
c1ccc(nc1)CN(Cc1ccccn1)Cc1ccccn1
NSC Number:
663674
Properties
Complexity:
262  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
290.153g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
290.37g/mol
Monoisotopic Mass:
290.153g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
41.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.6  
Literature
Title Journal
Kinetic and mechanistic aspects of atom transfer radical addition (ATRA) catalyzed by copper complexes with tris(2-pyridylmethyl)amine. Inorganic chemistry 20121105
Characterization of cobalt(III) hydroxamic acid complexes based on a tris(2-pyridylmethyl)amine scaffold: reactivity toward cysteine methyl ester. Inorganic chemistry 20120903
Improvement of durability of an organic photocatalyst in p-xylene oxygenation by addition of a Cu(II) complex. Physical chemistry chemical physics : PCCP 20120721
Capped-tetrahedrally coordinated Fe(II) and Co(II) complexes using a 'Click'-derived tripodal ligand: geometric and electronic structures. Inorganic chemistry 20120716
Synthesis, spectroscopic analysis and photolabilization of water-soluble ruthenium(III)-nitrosyl complexes. Dalton transactions (Cambridge, England : 2003) 20120714
Nonprecious metal catalysts for fuel cell applications: electrochemical dioxygen activation by a series of first row transition metal tris(2-pyridylmethyl)amine complexes. Inorganic chemistry 20120416
KLF10, transforming growth factor-β-inducible early gene 1, acts as a tumor suppressor. Biochemical and biophysical research communications 20120309
Evaluating the identity and diiron core transformations of a (μ-oxo)diiron(III) complex supported by electron-rich tris(pyridyl-2-methyl)amine ligands. Inorganic chemistry 20120220
100 picosecond diffraction catches structural transients of laser-pulse triggered switching in a spin-crossover crystal. Chemistry (Weinheim an der Bergstrasse, Germany) 20120213
Discrete complexes immobilized onto click-SBA-15 silica: controllable loadings and the impact of surface coverage on catalysis. Journal of the American Chemical Society 20120208
Transient infrared spectroscopy: a new approach to investigate valence tautomerism. Physical chemistry chemical physics : PCCP 20120114
Effect of berberine on p53 expression by TPA in breast cancer cells. Oncology reports 20120101
π Back-bonding of iron(II) complexes supported by tris(pyrid-2-ylmethyl)amine and its nitro-substituted derivatives. The journal of physical chemistry. A 20111124
Water oxidation by mononuclear ruthenium complexes with TPA-based ligands. Inorganic chemistry 20111107
Reactivity of copper(II)-alkylperoxo complexes. Dalton transactions (Cambridge, England : 2003) 20111028
Nickel(II) complexes of tripodal 4N ligands as catalysts for alkane oxidation using m-CPBA as oxidant: ligand stereoelectronic effects on catalysis. Dalton transactions (Cambridge, England : 2003) 20111007
Galvanic zinc-copper microparticles produce electrical stimulation that reduces the inflammatory and immune responses in skin. Archives of dermatological research 20111001
Synthesis and properties of oxo-carboxylato- and dioxo-bridged diosmium complexes of tris(2-pyridylmethyl)amine. Inorganic chemistry 20110919
Theoretical study of oxidation of cyclohexane diol to adipic anhydride by [Ru(IV)(O)(tpa)(H2O)]2+ complex (tpa ═ tris(2-pyridylmethyl)amine). Inorganic chemistry 20110704
(Naphthalene-2,3-diolato-κO,O')[tris-(2-pyridyl-meth-yl)amine-κN]cobalt(III) hexa-fluoridophosphate hemihydrate. Acta crystallographica. Section E, Structure reports online 20110701
Syntheses, emission properties and intramolecular ligand exchange of zinc complexes with ligands belonging to the tmpa family. Dalton transactions (Cambridge, England : 2003) 20110514
Dicyanido[tris-(2-pyridyl-meth-yl)amine]-cobalt(III) hexa-fluorido-phosphate. Acta crystallographica. Section E, Structure reports online 20110501
Mice lacking MSK1 and MSK2 show reduced skin tumor development in a two-stage chemical carcinogenesis model. Cancer investigation 20110301
A theoretical study on the exciton circular dichroism of propeller-like metal complexes of bipyridine and tripodal tris(2-pyridylmethyl)amine derivatives. Chirality 20110201
Tuning the conversion of cyclohexane into cyclohexanol/one by molecular dioxygen, protons and reducing agents at a single non-porphyrinic iron centre and chemical versatility of the tris(2-pyridylmethyl)amine TPAFe(II)Cl2 complex in mild oxidation chemistry. Dalton transactions (Cambridge, England : 2003) 20110107
Structural comparison of copper(I) and copper(II) complexes with tris(2-pyridylmethyl)amine ligand. Inorganic chemistry 20101115
Regulation of differentiation by a PHD domain in the NUP98-PHF23 fusion protein. Leukemia research 20100801
Evaluation of diuron (3-[3,4-dichlorophenyl]-1,1-dimethyl urea) in a two-stage mouse skin carcinogenesis assay. Toxicologic pathology 20100801
A novel imaging approach for early detection of prostate cancer based on endogenous zinc sensing. Cancer research 20100801
Development of highly sensitive fluorescent probes for detection of intracellular copper(I) in living systems. Journal of the American Chemical Society 20100505
Synthesis and characterization of ruthenium(II)-pyridylamine complexes with catechol pendants as metal binding sites. Inorganic chemistry 20100419
Reductive coupling of nitrogen monoxide (*NO) facilitated by heme/copper complexes. Inorganic chemistry 20100215
Investigation and improvement of DNA cleavage models of polyamide + Cu(II) nuclease + OOH- ligands bound to DNA. BMC structural biology 20100101
(Mu-eta2:eta2-disulfido)dinickel(II) complexes supported by 6-methyl-TPA ligands. Dalton transactions (Cambridge, England : 2003) 20091121
Biomimetic interaction between Fe(II) and O2: effect of the second coordination sphere on O2 binding to Fe(II) complexes: evidence of coordination at the metal centre by a dissociative mechanism in the formation of mu-oxo diferric complexes. Chemistry (Weinheim an der Bergstrasse, Germany) 20091012
Observed enhancement of the reactivity of a biomimetic diiron complex by the addition of water - mechanistic insights from theoretical modeling. Dalton transactions (Cambridge, England : 2003) 20090914
A [4+2] mixed ligand approach to ruthenium DNA metallointercalators [Ru(tpa)(N-N)](PF(6))(2) using a tris(2-pyridylmethyl)amine (tpa) capping ligand. Journal of inorganic biochemistry 20090801
Polymorphism in the spin-crossover ferric complexes [(TPA)Fe(III)(TCC)]PF6. Acta crystallographica. Section B, Structural science 20090801
Bis(thio-cyanato-κN)[tris-(2-pyridylmeth-yl)amine-κN,N',N'',N''']nickel(II) methanol hemisolvate. Acta crystallographica. Section E, Structure reports online 20090701
Regiospecific intramolecular O-demethylation of the ligand by action of molecular dioxygen on a ferrous complex: versatile coordination chemistry of dioxygen in FeCl(2) complexes with (2,3-dimethoxyphenyl) alpha-substituted tripods in the tris(2-pyridylmethyl)amine series. Inorganic chemistry 20090601
Surface-initiated activators generated by electron transfer for atom transfer radical polymerization in detection of DNA point mutation. Analytical chemistry 20090601
Observation of redox-induced electron transfer and spin crossover for dinuclear cobalt and iron complexes with the 2,5-di-tert-butyl-3,6-dihydroxy-1,4-benzoquinonate bridging ligand. Journal of the American Chemical Society 20090506
Polynuclear spin crossover complexes: synthesis, structure, and magnetic behavior of [Fe4(mu-CN)4(phen)4(L)2)]4+ squares. Inorganic chemistry 20090420
Possible steric control of the relative strength of chelation enhanced fluorescence for zinc(II) compared to cadmium(II): metal ion complexing properties of tris(2-quinolylmethyl)amine, a crystallographic, UV-visible, and fluorometric study. Inorganic chemistry 20090216
Two transition metal coordination polymers of the 7,7,8,8-tetracyanoquinodimethane dianion (TCNQ2-). Acta crystallographica. Section C, Crystal structure communications 20090101
Anti-inflammatory and arthritic effects of thiacremonone, a novel sulfur compound isolated from garlic via inhibition of NF-kappaB. Arthritis research & therapy 20090101
The preparation and full characterization of dichloroferrous complexes of mono-, bis- and tris-alpha-methyl substituted tris(2-pyridylmethyl)amine (TPA) ligands. Structural bases of stability of the complexes in solution. Dalton transactions (Cambridge, England : 2003) 20081228
The effect and influence of cis-ligands on the electronic and oxidizing properties of nonheme oxoiron biomimetics. A density functional study. The journal of physical chemistry. A 20081218
H2O2-reactivity of copper(II) complexes supported by tris[(pyridin-2-yl)methyl]amine ligands with 6-phenyl substituents. Inorganic chemistry 20081215
Synthesis and characterization of mononuclear hydroxamato and hydroximato complexes of iron(III) based on the tris-(2-pyridylmethyl)amine ligand. Dalton transactions (Cambridge, England : 2003) 20081207
The effects of pressure on valence tautomeric transitions of dinuclear cobalt complexes. Chemical communications (Cambridge, England) 20081207
2,2',2''-[Nitrilo-tris(methyl-ene-p-phenyl-ene)]tribenzonitrile. Acta crystallographica. Section E, Structure reports online 20081001
Quantitative proliferation dynamics and random chromosome segregation of hair follicle stem cells. The EMBO journal 20080507
Berberine inhibits TPA-induced MMP-9 and IL-6 expression in normal human keratinocytes. Phytomedicine : international journal of phytotherapy and phytopharmacology 20080501
Suggestion of an organometallic intermediate in an intramolecular dechlorination reaction involving copper(I) and a ArCH2Cl moiety. Journal of the American Chemical Society 20080430
Iron(II) complexes of sterically bulky alpha-ketocarboxylates. structural models for alpha-ketoacid-dependent nonheme iron halogenases. Inorganic chemistry 20080218
A dinuclear iron(II) complex, [(TPyA)FeII(THBQ(2-))FeII(TPyA)](BF4)2 [TPyA = tris(2-pyridylmethyl)amine; THBQ(2-) = 2,3,5,6-tetrahydroxy-1,4-benzoquinonate] exhibiting both spin crossover with hysteresis and ferromagnetic exchange. Chemical communications (Cambridge, England) 20080121
Proton-coupled electron transfer in ruthenium(II)-pterin complexes: formation of ruthenium-coordinated pterin radicals and their electronic structures. Inorganic chemistry 20080107
Contrasting cis and trans effects on the reactivity of nonheme oxoiron(IV) complexes. Angewandte Chemie (International ed. in English) 20080101
Reactivity of molecular dioxygen towards a series of isostructural dichloroiron(III) complexes with tripodal tetraamine ligands: general access to mu-oxodiiron(III) complexes and effect of alpha-fluorination on the reaction kinetics. Chemistry (Weinheim an der Bergstrasse, Germany) 20080101
μ-Oxido-bis-{chlorido[tris-(2-pyridylmeth-yl)amine]chromium(III)} bis(hexafluoridophosphate). Acta crystallographica. Section E, Structure reports online 20080101
μ-Oxido-bis-{chlorido[tris-(2-pyridylmethyl)amine]manganese(III)} bis-(hexa-fluorido-phosphate). Acta crystallographica. Section E, Structure reports online 20080101
Copper(I) complex O(2)-reactivity with a N(3)S thioether ligand: a copper-dioxygen adduct including sulfur ligation, ligand oxygenation, and comparisons with all nitrogen ligand analogues. Inorganic chemistry 20070723
Atom transfer radical addition in the presence of catalytic amounts of copper(I/II) complexes with tris(2-pyridylmethyl)amine. Inorganic chemistry 20070723
Ligand effects on dioxygen activation by copper and nickel complexes: reactivity and intermediates. Accounts of chemical research 20070701
Aryl hydroxylation from a mononuclear copper-hydroperoxo species. Journal of the American Chemical Society 20070606
Copper(II)-hydroperoxo complex induced oxidative N-dealkylation chemistry. Journal of the American Chemical Society 20070530
Generation and characterization of [(P)M-(X)-Co(TMPA)]n+ assemblies; P = Porphyrinate, M = FeIII and CoIII, X = O2-, OH-, O2(2-), and TMPA = tris(2-pyridylmethyl)amine. Inorganic chemistry 20070416
Kinetic analysis of the conversion of nonheme (alkylperoxo)iron(III) species to iron(IV) complexes. Inorganic chemistry 20070402
Ligand effects on Ni(II)-catalysed alkane-hydroxylation with m-CPBA. Dalton transactions (Cambridge, England : 2003) 20070321
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Synthesis, structure, and magnetic properties of valence ambiguous dinuclear antiferromagnetically coupled cobalt and ferromagnetically coupled iron complexes containing the chloranilate(2-) and the significantly stronger coupling chloranilate(*3-) radical trianion. Journal of the American Chemical Society 20070227
Room-temperature spin crossover observed for [(TPyA)FeII(DBQ(2-))Fe(II)(TPyA)](2+) [TPyA = Tris(2-pyridylmethyl)amine; DBQ(2-) = 2,5-Di-tert-butyl-3,6-dihydroxy-1,4-benzoquinonate]. Inorganic chemistry 20070219
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Dioxygen reactivity of a copper(I) complex with a N3S thioether chelate; peroxo-dicopper(II) formation including sulfur-ligation. Inorganic chemistry 20061211
Syntheses, characterization, and catalytic ability in alkane oxygenation of chloro(dimethyl sulfoxide)ruthenium(II) complexes with tris(2-pyridylmethyl)amine and its derivatives. Inorganic chemistry 20061002
Rapid induction of skin tumors in human but not mouse c-Ha-ras proto-oncogene transgenic mice by chemical carcinogenesis. Cancer science 20060901
The coordination chemistry of FeCl3 and FeCl2 to bis[2-(2,3-dihydroxyphenyl)-6-pyridylmethyl](2-pyridylmethyl)amine: access to a diiron(III) compound with an unusual pentagonal-bipyramidal/square-pyramidal environment. Chemistry (Weinheim an der Bergstrasse, Germany) 20060825
Rhodium, palladium and platinum complexes of tris(pyridylalkyl)amine and tris(benzimidazolylmethyl)amine N4-tripodal ligands. Dalton transactions (Cambridge, England : 2003) 20060821
Efficient synthesis of calix[6]tmpa: a new calix[6]azacryptand with unique conformational and host-guest properties. Chemistry (Weinheim an der Bergstrasse, Germany) 20060816
Nonheme oxoiron(IV) complexes of tris(2-pyridylmethyl)amine with cis-monoanionic ligands. Inorganic chemistry 20060807
Oxoiron(IV) complexes of the tris(2-pyridylmethyl)amine ligand family: effect of pyridine alpha-substituents. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20060401
A sensitive probe for the detection of Zn(II) by time-resolved fluorescence. Journal of the American Chemical Society 20060329
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Stabilization of coordinated carbonate in aqueous acidic solution: steric inhibition of protonation in Co(III) complexes containing chelated carbonate. Inorganic chemistry 20060320
Density functional study of the O2 binding to [CuI(TPAR)]+ (TPA = tris(2-pyridylmethyl)amine) in THF and EtCN. Inorganic chemistry 20060220
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Activity-dependent subcellular localization of NAC1. The European journal of neuroscience 20050701
Controlled hydrolysis of lanthanide complexes of the N-donor tripod tris(2-pyridylmethyl)amine versus bisligand complex formation. Inorganic chemistry 20050627
Spin crossover of ferric complexes with catecholate derivatives. Single-crystal X-ray structure, magnetic and Mössbauer investigations. Dalton transactions (Cambridge, England : 2003) 20050505
Src homology domains in phospholipase C-gamma1 mediate its anti-apoptotic action through regulating the enzymatic activity. Journal of neurochemistry 20050501
Mononuclear oxovanadium complexes of tris(2-pyridylmethyl)amine. Dalton transactions (Cambridge, England : 2003) 20050421
Heme/non-heme diiron(II) complexes and O2, CO, and NO adducts as reduced and substrate-bound models for the active site of bacterial nitric oxide reductase. Journal of the American Chemical Society 20050316
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A linear correlation between energy of LMCT band and oxygenation reaction rate of a series of catecholatoiron(III) complexes: initial oxygen binding during intradiol catechol oxygenation. Journal of inorganic biochemistry 20050301
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Designing dinuclear iron(II) spin crossover complexes. Structure and magnetism of dinitrile-, dicyanamido-, tricyanomethanide-, bipyrimidine- and tetrazine-bridged compounds. Dalton transactions (Cambridge, England : 2003) 20041021
Glutamate-dependent transcriptional regulation of GLAST: role of PKC. Journal of neurochemistry 20041001
Mono-, bi-, and trinuclear CuII-Cl containing products based on the tris(2-pyridylmethyl)amine chelate derived from copper(I) complex dechlorination reactions of chloroform. Inorganic chemistry 20040920
TIS21/BTG2/PC3 is expressed through PKC-delta pathway and inhibits binding of cyclin B1-Cdc2 and its activity, independent of p53 expression. Experimental cell research 20040910
Epidermal growth factor upregulates matrix metalloproteinase-7 expression through activation of PEA3 transcription factors. International journal of oncology 20040601
Photoassisted oxygenation of alkane catalyzed by ruthenium complexes using 2,6-dichloropyridine N-oxide under visible light irradiation. Chemical communications (Cambridge, England) 20040407
Toward a photochemical and thermal molecular machine: reversible ligand dissociation and binding in a ruthenium(II)-2,2'-bipyridine complex with tris(2-pyridylmethyl)amine. Inorganic chemistry 20040405
Geometry-dependent phosphodiester hydrolysis catalyzed by binuclear copper complexes. Inorganic chemistry 20031201
Chromium(II) and chromium(III) complexes supported by tris(2-pyridylmethyl)amine: synthesis, structures, and reactivity. Inorganic chemistry 20031020
The rate of O2 and CO binding to a copper complex, determined by a 'flash-and-trap' technique, exceeds that for hemes. Journal of the American Chemical Society 20031001
Protein kinase C inhibition induces DNA fragmentation in COLO 205 cells which is blocked by cysteine protease inhibition but not mediated through caspase-3. Experimental cell research 20030910
A dramatic push effect on the homolysis of FeIII(OOR) intermediates to form non-heme FeIV=O complexes. Angewandte Chemie (International ed. in English) 20030811
Atypical protein kinase C mediates activation of NF-E2-related factor 2 in response to oxidative stress. American journal of physiology. Cell physiology 20030801
Inhibition of caspase-9 through phosphorylation at Thr 125 by ERK MAPK. Nature cell biology 20030701
Spectroscopic study of [Fe2O2(5-Et3-TPA)2]3+: nature of the Fe2O2 diamond core and its possible relevance to high-valent binuclear non-heme enzyme intermediates. Journal of the American Chemical Society 20030618
Synthesis and characterization of reduced heme and heme/copper carbonmonoxy species. Inorganic chemistry 20030505
Copper(I)-dioxygen reactivity of [(L)Cu(I)](+) (L = tris(2-pyridylmethyl)amine): kinetic/thermodynamic and spectroscopic studies concerning the formation of Cu-O2 and Cu2-O2 adducts as a function of solvent medium and 4-pyridyl ligand substituent variations. Inorganic chemistry 20030324
Biomimetic aryl hydroxylation derived from alkyl hydroperoxide at a nonheme iron center. Evidence for an Fe(IV)=O oxidant. Journal of the American Chemical Society 20030226
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Overexpression of telomerase confers a survival advantage through suppression of TRF1 gene expression while maintaining differentiation characteristics in K562 cells. Cell transplantation 20030101
Trigonal bipyramidal geometry and tridentate coordination mode of the tripod in FeCl(2) complexes with tris(2-pyridylmethyl)amine derivatives bis-alpha-substituted with bulky groups. structures and spectroscopic comparative studies. Inorganic chemistry 20021021
A density functional study of O-O bond cleavage for a biomimetic non-heme iron complex demonstrating an Fe(v)-intermediate. Journal of the American Chemical Society 20020918
Electronic structure and reactivity of low-spin Fe(III)-hydroperoxo complexes: comparison to activated bleomycin. Journal of the American Chemical Society 20020911
Oxidative strand scission of nucleic acids by a multinuclear copper(II) complex. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20020901
Anion sensing with luminescent lanthanide complexes of tris(2-pyridylmethyl)amines: pronounced effects of lanthanide center and ligand chirality on anion selectivity and sensitivity. Chemical communications (Cambridge, England) 20020607
Human Krüppel-like factor5/KLF5: synergy with NF-kappaB/Rel factors and expression in human skin and hair follicles. European journal of cell biology 20020601
Efficient and specific strand scission of DNA by a dinuclear copper complex: comparative reactivity of complexes with linked tris(2-pyridylmethyl)amine moieties. Journal of the American Chemical Society 20020529
Synthesis, structures, and magnetic properties of heterodimetal bis(mu-hydroxo)chromium(III)nickel(II) complexes with Tpa derivatives having sterically bulky substituents. Inorganic chemistry 20020325
Electronic structure of high-spin iron(III)-alkylperoxo complexes and its relation to low-spin analogues: reaction coordinate of O-O bond homolysis. Journal of the American Chemical Society 20011226
Spectroscopic properties and electronic structure of low-spin Fe(III)-alkylperoxo complexes: homolytic cleavage of the O-O bond. Journal of the American Chemical Society 20010829
Tridentate coordination of monosubstituted derivatives of the tris(2-pyridylmethyl)amine ligand to FeCl3: structures and spectroscopic properties of ((2-bromopyridyl)methyl)bis-(2-pyridylmethyl)amine Fe(III)Cl3 and (((2-p-methoxyphenyl)pyridyl)methyl)bis(2-pyridyl-methyl)]amine Fe(III)Cl3 and comparison with the bis(2-pyridylmethyl)]amine Fe(III)Cl3 complex. Inorganic chemistry 20010827
Stereospecific alkane hydroxylation by non-heme iron catalysts: mechanistic evidence for an Fe(V)=O active species. Journal of the American Chemical Society 20010704
Copper(I) complexes, copper(I)/O(2) reactivity, and copper(II) complex adducts, with a series of tetradentate tripyridylalkylamine tripodal ligands. Inorganic chemistry 20010507
Properties