3682-35-7

Basic information

• Product Name: 2,4,6-Tris(2-pyridyl)-1,3,5-triazine
• Synonyms: 1,3,5-Triazine, 2,4,6-tri-2-pyridinyl-;2,4,6-Tri(2-pyridinyl)-1,3,5-triazine;2,4,6-tri-2-pyridinyl-1,3,5-triazine;2,4,6-tri-2-pyridyl-s-triazin;2,4,6-Tris(2-pyridyl)-5-triazine;5-triazine,2,4,6-tri-2-pyridinyl-3;s-Triazine, 2,4,6-tri-2-pyridyl-;s-Triazine, tri-2-pyridyl-
• CAS NO: 3682-35-7
• Molecular Formula: C₁₈H₁₂N₆
• Molecular Weight: 312.33
• EINECS: 222-965-9
• Product Categories: Organics;marker
• Mol File: 3682-35-7.mol

Chemical Properties

• Melting Point: 247-249 °C(lit.)
• Boiling Point: 442.26°C (rough estimate)
• Flash Point: 288.2 °C
• Appearance: Yellow/Powder
• Density: 1.276
• Vapor Pressure: 1.41E-14mmHg at 25°C
• Refractive Index: 1.4570 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: 100 mg/mL, clear
• PKA: 1.14±0.19(Predicted)
• Merck: 14,9750
• BRN: 282581
• CAS DataBase Reference: 2,4,6-Tris(2-pyridyl)-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Tris(2-pyridyl)-1,3,5-triazine(3682-35-7)
• EPA Substance Registry System: 2,4,6-Tris(2-pyridyl)-1,3,5-triazine(3682-35-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: XZ2050000
• TSCA: Yes
• Hazardous Substances Data: 3682-35-7(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
TPTZ is used as a spectrophotometric reagent for the determination of phenols and pharmaceutical drugs. Its ability to undergo exudation under experimental conditions makes it a valuable tool in this field.
Used in Iron Determination:
TPTZ is used as a colorimetric reagent for the detection and measurement of iron concentration. When combined with ferrous ions, it forms a complex that allows for the spectrophotometric determination of acetaminophen in samples of serum and plasma.
Used in Pharmaceutical Research:
Due to its interaction with biopolymers and macromolecules, TPTZ is also used as a research tool in the pharmaceutical industry, particularly for the development of new drugs and therapies.

Purification Methods

Purify it by repeated crystallisation from aqueous EtOH. It is a reagent for the determination of Fe(II) and total Fe [Collins et al. Anal Chem 31 1862 1959]. [Beilstein 26 III/IV 4192.]

InChI:InChI=1/C18H12N6/c1-4-10-19-13(7-1)16-22-17(14-8-2-5-11-20-14)24-18(23-16)15-9-3-6-12-21-15/h1-12H

Synthetic route

2-Cyanopyridine (100-70-9) → 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7)

Conditions	Yield
With ammonia; lanthanum(lll) triflate at 200℃; for 24h; in a stainless steel pressure vessel;	100%
With sodium hydride at 180℃;	67%
With sodium hydride at 160 - 165℃;

2-Cyanopyridine (100-70-9) + 3-Aminomethylpyridine (3731-52-0) → 2,4-bis(2-pyridyl)-5-(3-pyridyl)imidazole (1198018-55-1) + N-(3-(3-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (1198018-58-4) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7)

Conditions	Yield
Stage #1: 2-Cyanopyridine; 3-Aminomethylpyridine at 100℃; for 12h; Stage #2: With potassium hydroxide In water for 12h;	A 75% B 5% C 20%

2-Cyanopyridine (100-70-9) + (2-aminomethylpyridine) (3731-51-9) → 2,2',2''-(1H-imidazole-2,4,5-triyl)tripyridine (23974-92-7) + N-(3-(2-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (1198018-57-3) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7)

Conditions	Yield
Stage #1: 2-Cyanopyridine; 2-(Aminomethyl)pyridine at 100℃; for 12h; Stage #2: With potassium hydroxide In water for 12h;	A 73% B 5% C 20%

2-Cyanopyridine (100-70-9) + 4-(aminomethyl)pyridine (3731-53-1) → 2,4-bis(2-pyridyl)-5-(4-pyridyl)imidazole (1198018-56-2) + N-(3-(4-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (1198018-59-5) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7)

Conditions	Yield
Stage #1: 2-Cyanopyridine; 4-(aminomethyl)pyridine at 100℃; for 12h; Stage #2: With potassium hydroxide In water for 12h;	A 73% B 4.5% C 20%

pyridine-2-carbaldehyde (1121-60-4) → pyridine-2-carboxylic acid amide (1452-77-3) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7)

Conditions	Yield
With ammonium hydroxide; potassiuim nitrosodisulfonate In pyridine for 144h; Ambient temperature;	A 34% B 40%

2-Cyanopyridine (100-70-9) + NaH → 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7)

Conditions	Yield
at 160 - 165℃;

rhenium(I) pentacarbonyl chloride (14099-01-5) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Re(CO)3(2,4,6-tris(2-pyridyl)-1,3,5-triazine)Cl] (226896-03-3)

Conditions	Yield
In toluene the mixt. in toluene was refluxed under N2 for 4 h, cooled; ppt. was filtered, stirred in DCM for 10 min, filtered, washed with CH2Cl2 and diethyl ether, dried in vac.;	99%

methanol (67-56-1) + copper(II) choride dihydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → CuCl2 [2,4,6-tris(2-pyridyl)-1,3,5-triazine]CuCl2(methanol) (738606-13-8)

Conditions	Yield
In methanol solid ligand and 15 equiv. of solid CuCl2 dissolved in CH3OH slowly diffused into each other for 7 d; elem. anal.;	97%

2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → 2,4-di(pyridin-1-ium-2-yl)-6-(2-pyridyl)-1,3,5-triazine bis(hexafluorophosphate) monohydrate

Conditions	Yield
Stage #1: 2,4,6-tris(2-pyridyl)-1,3,5-triazine With ammonium hexafluorophosphate In methanol at 20℃; for 0.166667h; Stage #2: With sulfuric acid at 20℃; for 2h;	96%

tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (161265-03-8) → [Cu2(2,4,6-tri(pyridin-2-yl)-1,3,5-triazine)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)2][PF6]2

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane for 2h; Stage #2: 2,4,6-tris(2-pyridyl)-1,3,5-triazine In dichloromethane for 2h;	93.6%

2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + scandium(III) chloride → trichloro[2,4,6-tris(α-pyridyl)-1,3,5-triazine]scandium(III)

Conditions	Yield
In acetonitrile The mixt. was boiled under reflux for 1 h;; filtered, washed with CH3CN, dried at 0.005 mmHg at 60°C.; elem.anal.;	93%

2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → N-2-pyridinylcarbonyl-2-pyridinecarboximide (6707-97-7)

Conditions	Yield
Stage #1: 2,4,6-tris(2-pyridyl)-1,3,5-triazine With water; copper diacetate at 70℃; Stage #2: With C10H13N2O8(3-)*2Na(1+)*H(1+) In chloroform; water at 20℃; for 2h;	91%
Stage #1: 2,4,6-tris(2-pyridyl)-1,3,5-triazine With water; copper(II) nitrate Stage #2: With disodium ethylenediamine tetraacetic acid

sodium azide + manganese(II) perchlorate hexahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Mn(2,4,6-tris(2-pyridyl)-1,3,5-triazine)(μ-1,1-N3)2](n)

Conditions	Yield
In methanol; water a methanolic soln. of triazine-compound was slowly added to an aq. soln.of Mn(ClO4)2*6H2O, stirrred for few min at room temp., aq. NaN3 was add ed dropwise with stirring; filtered, was kept at room temp. for 4 days; elem. anal.;	90%

manganese(II) perchlorate hexahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + sodium thiocyanide (540-72-7) → [Mn(2,4,6-tris(2-pyridyl)-1,3,5-triazine)(thiocyanato)2(H2O)] (944049-02-9)

Conditions	Yield
In methanol; water stirring of aq. soln. of Mn(ClO4)2*6H2O with methanolic soln. of 2,4,6-tris(2-pyridyl)-1,3,5-triazine; addn. of aq. soln. of NaNCS; stirring for20 min; filtration, crystn. for 7 ds; elem. anal.;	90%

methanol (67-56-1) + trans-bis[O-methyl-(4-methoxyphenyl)phosphonodithioato]nickel (736141-91-6, 195193-91-0) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Ni(MeOpdt)2(2,4,6-tris(2-pyridyl)-1,3,5-triazine)]*MeOH (943720-33-0)

Conditions	Yield
In methanol ligand and Ni-complex refluxed for 1 h in MeOH; slow evapd. at room temp.; elem. anal.;	90%

tris(triphenylphosphine)ruthenium(II) chloride (15529-49-4, 41756-81-4) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Ru(κ3-2,4,6-tris(2-pyridyl)-1,3,5-triazine)(triphenylphosphine)Cl2] (1007586-89-1)

Conditions	Yield
In benzene (N2); a suspn. of Ru complex treated with ligand, refluxed for 4 h; filtered, washed (C6H6, Et2O), dried (vac.); elem. anal.;	90%

vanadyl(IV) sulfate hydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → dioxo(bis(2-pyridylcarbonyl)amido)vanadium(V)

Conditions	Yield
With L-leucine; salicylaldehyde; potassium hydroxide In methanol; water for 2h; pH=7.5 - 8;	90%

manganese(II) chloride tetrahydrate + ethanol (64-17-5) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + thiourea (17356-08-0) → C20H17Cl2MnN6O*CH4N2S

Conditions	Yield
In water at 80℃; pH=5 - 6;	90%

erbium(III) chloride hexahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + 1,3-diphenylpropanedione (120-46-7) → Er(dibenzoylmethane)3(2,4,6-tri(2-pyridyl)-1,3,5-triazine)

Conditions	Yield
With t-BuOK In ethanol mixt. of N compd. and lanthanide salt in abs. EtOH stirred under reflux for 30 min, soln. of t-BuOK and diketone added, stirred for 1 h at 50°C, then at room temp. for 30 min; EtOH removed in vac., residue washed with water, solid dissolved in CHCl3, dried over anhydr. MgSO4, filtered, solvent removed, recrystd. from EtOH/CHCl3 (2:1); elem. anal.;	88.8%

samarium diiodide + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → Sm2(2,4,6-tris(2-pyridyl)-1,3,5-triazine-2,4,6-tris(2-pyridyl)-1,3,5-triazine)I4

Conditions	Yield
In acetonitrile (under Ar); SmI2 mixed with ligand and MeCN, heated at 100°C for 10 h; filtered, washed with MeCN, dried under vac.; elem. anal.;	88%
In pyridine (under Ar); SmI2 mixed with ligand and pyridine, heated at 100°C for 10 h, solvent evapd., MeCN added, stirred for 12 h; elem. anal.;	81%

iron(III) chloride + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + thiourea (17356-08-0) → [Fe(2,4,6-tris-(2-pyridyl)-1,3,5-triazine)Cl3]thiourea

Conditions	Yield
In ethanol; water at 80℃; pH=5 - 6;	88%

2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + water (7732-18-5) + nitric acid (7697-37-2) + manganese(II) acetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → [Mn(acetato)(H2O)3(2,4,6-tris(2-pyridyl)-1,3,5-triazine)](NO3)*0.1H2O

Conditions	Yield
In H2O dissolving of Mn(CH3COO)2 and 2,4,6-tris(2-pyridyl)-1,3,5-triazine in H2O; stirring for 2 h at room temp.; addn. of HNO3; crystn. for 10 ds; elem. anal.;	87%

2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + water (7732-18-5) + nitric acid (7697-37-2) + manganese(II) acetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → [Mn(acetato)(H2O)3(2,4,6-tris(2-pyridyl)-1,3,5-triazine)](NO3) (1259927-31-5)

Conditions	Yield
In water; nitric acid aq. HNO3; Mn(OAc)2 and triazine was stirred in water for 2 h at room temp., 0.1 M HNO3 was added; crystals were obtained after 10 d, elem. anal.;	87%

chromium(III) chloride hexahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [CrIII(2,4,6-tri-(2-pyridyl)-1,3,5-triazine)Cl2(H2O)1/2]Cl*1/2EtOH

Conditions	Yield
In ethanol for 2h; Reflux;	87%

ammonium tetrafluroborate (13826-83-0) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → (((η6-p-cymene)RuCl)2(2,4,6-tris(2-pyridyl)-1,3,5-triazine))(BF4)2

Conditions	Yield
In methanol under N2 atm. suspn. Ru complex in MeOH was treated with ligand (1:1) and stirred at r.t. for 4 h, soln. was filtered, soln. NH4BF4 in MeOH was added; soln. was left in refrigerator for crystn., ppt. was filtered, washed with MeOH, Et2O, and dried in vacuo, recrystd. from acetone-Et2O; elem. anal.;	85%

ammonium hexafluorophosphate + trichloro(2,2':6',2''-terpyridine)rhodium(III) (35978-56-4) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Rh(bis(2-pyridylcarbonyl)amide)(2,2':6',2''-terpyridine)][PF6]2

Conditions	Yield
In ethanol; water refluxing Rh-complex with triazine ligand in EtOH/water=2:1 for 24 h, concn. (reduced pressure), pptn. on addn. of aq. NH4PF6; collection (filtration), washing (water), recrystn. (MeCN); elem. anal.;	85%

rhodium(III) chloride trihydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Rh(2,4,6-tris-(2-pyridyl)-1,3,5-triazine)Cl3] * 2 H2O

Conditions	Yield
In ethanol refluxing equimolar amts. for 2 h (pptn.); collection (filtration), washing (water, hot EtOH, Et2O), recrystn. (boiling MeCN); elem. anal.;	85%

manganese(II) chloride tetrahydrate + manganese (II) nitrate tetrahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Mn(2,4,6-tris(2-pyridyl)-1,3,5-triazine)Cl(H2O)]*0.5H2O

Conditions	Yield
In methanol; water addn. of aq. soln. of Mn(NO3)2*4H2O and MnCl2*4H2O to soln. of 2,4,6-tris(2-pyridyl)-1,3,5-triazine in MeOH; stirring at 35°C; cooling, pptn., dissolving in DMF; filtration, crystn. for 5 ds; elem. anal.;	85%

hydrogenchloride (7647-01-0) + methanol (67-56-1) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + molybdenum(VI) oxide → [cis-dioxotrichloridomethanolmolybdenum(VI)]·[2,2′,2″-(1,3,5-triazine-2,4,6-triyl)tripyridinium]·Cl2

Conditions	Yield
Stage #1: hydrogenchloride; molybdenum(VI) oxide In water at 70℃; Stage #2: methanol; 2,4,6-tris(2-pyridyl)-1,3,5-triazine In water at 20℃; for 216h;	85%

cobalt(II) chloride hexahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Co(2,4,6-tris(2-pyridyl)-1,3,5-triazine)Cl2]*2H2O

Conditions	Yield
In ethanol for 3h; Reflux;	85%

cobalt(II) chloride hexahydrate + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + water (7732-18-5) + thiourea (17356-08-0) → [Co(2,4,6-tris-(2-pyridyl)-1,3,5-triazine)Cl2(H2O)]thiourea.1/2H2O

Conditions	Yield
In ethanol at 80℃; pH=5 - 6;	85%

2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) + water (7732-18-5) + sodium dicyanamide (1934-75-4) + cobalt(II) perchlorate hexahydrate → [Co(dicyanamide)(2,4,6-tris(2-pyridyl)-1,3,5-triazine)(H2O)]2(ClO4)2

Conditions	Yield
In methanol; water MeOH soln. of pyrazine deriv. added to aq. Co perchlorate and NaNCNCN with stirring for 20 min; filtered; filtrate kept at room temp. for 5 d; elem. anal.;	84%

methanol (67-56-1) + Y(3+)*3NCS(1-)*6H2O=Y(NCS)3*6H2O + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [Y(H2O)3(2,4,6-tris(2-pyridyl)-s-triazine)(NCS)2]·NCS·(2,4,6-tris(2-pyridyl)-s-triazine)·1.5H2O·1.25MeOH

Conditions	Yield
In water	84%

rhenium(I) pentacarbonyl bromide (14220-21-4) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → [ReBr(CO)3(2,4,6-tris(2-pyridyl)-1,3,5-triazine)] (349532-84-9)

Conditions	Yield
In chloroform Re-complex and ligand in CHCl3 were heated to reflux under N2 for 3 h, cooled to room temp.; filtered, evapd. to dryness, recrystd. from MeOH; elem. anal.;	83%

neodymium(III) chloride hexahydrate + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + 2,4,6-tris(2-pyridyl)-1,3,5-triazine (3682-35-7) → tris(1,1,1,5,5,5-hexafluoro-2,4-pentanedionato)(2,4,6-tris(2-pyridyl)-1,3,5-triazine)neodimium(III) (1255793-11-3)

Conditions	Yield
With NH4OH In ethanol 1,1,1,5,5,5-hexafluoro-2,4-pentanedione in EtOH added to NH4OH soln., treated with EtOH soln. of 2,4,6-tris(2-pyridyl)-1,3,5-triazine and NdCl3*6H2O (Hhfaa:NH4OH:tpz:La=3:3:1:1), stirred at room temp. for 5 h; filtered, crystd. for 3 d, filtered, washed (CCl4), recrystd. twice (EtOH), dried (vac. P4O10), elem. anal.;	83%

Upstream product

• 100-70-9 2-Cyanopyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 3731-53-1 4-(aminomethyl)pyridine 
• 3731-52-0 3-Aminomethylpyridine 
• 3731-51-9 2-(Aminomethyl)pyridine 

Downstream Products

• 117681-70-6 (catecholato)SbF(2,4,6-tris(2-pyridyl)-1,3,5-triazine) 
• 189445-46-3 cis-bis(4-trifluoromethyl2,3,5,6-tetrafluorophenyl)(2,4,6-tris(2-pyridyl)-1,3,5-triazine)platinum(II) 
• 189445-47-4 cis-bis(4-trifluoromethyl2,3,5,6-tetrafluorophenyl)(2,4,6-tris(2-pyridyl)-1,3,5-triazine)palladium(II) 
• 697300-47-3 [ruthenium(II)(η5-cyclopentadienyl)(triphenylphosphine)(1,3,5-tris(pyridyl)1,4,6-triazine)]PF6 
• 861393-84-2 OsCl(P(C₆H₅)3)2(C₅H₄N)3C₃N₃⁽¹⁺⁾*BF₄^(1-)*H₂O=OsCl(P(C₆H₅)3)2(C₅H₄N)3C₃N₃BF₄*H₂O 
• 782502-91-4 [Ir(hydrido)2(triphenylphosphine)2(2,4,6-tris(2-pyridyl)-1,3,5-pyridyltriazine)](PF₆) 
• 861393-87-5 OsCl(As(C₆H₅)3)2(C₅H₄N)3C₃N₃⁽¹⁺⁾*BF₄^(1-)=OsCl(As(C₆H₅)3)2(C₅H₄N)3C₃N₃BF₄ 
• 31378-26-4 tris(2,4-pentanedionato)ruthenium(III) 
• 882072-06-2 [Ru(II)(2,4,6-tris(2-pyridyl)-1,3,5-triazine)(acetylacetonate)(MeCN)]ClO₄ 
• 913701-26-5 [Ru(PPh₃)2(2,4,6-tris(2-pyridyl)-1,3,5-triazine)Cl]PF₆ 
• 959850-39-6 [Cu(bis(2-pyridylcarbonyl)amide)(2-chlorobenzoate)(H₂O)] 
• 959850-41-0 [Cu(bis(2-pyridylcarbonyl)amide)(3-chlorobenzoate)] 
• 943720-33-0 [Ni(MeOpdt)2(2,4,6-tris(2-pyridyl)-1,3,5-triazine)]*MeOH 

Relevant articles and documents

Catalytic trimerization of 2- and 4-cyanopyridine isomers to the triazine derivatives in presence of magnesium phthalocyanine

The crystals of 2,4,6-tris(2-pyridyl)-1,3,5-triazine and 2,4,6-tris(4-pyridyl)-1,3,5-triazine isomers have been obtained by a catalytic trimerization of 2- and 4-cyanopyridine in presence of magnesium phthalocyanine. For the 2,4,6-tris(2-pyridyl)-1,3,5-triazine isomer there are two possible conformations that differ in the positions of the N atoms in pyridine rings in relation to the triazine ring. These conformations differ by ～11.30 kJ mol-1 as shown by the molecular orbital calculations. The 2,4,6-tris(2-pyridyl)-1,3,5-triazine crystallises in the centrosymmetric space group of the triclinic system, while the 2,4,6-tris(4-pyridyl)-1,3,5-triazine isomer crystallises in the C2/c space group of monoclinic system. The 2,4,6-tris(2-pyridyl)-1,3,5-triazine molecule is non-planar in the crystal, due to the steric effect of lone-pair electron at the N atom in both pyridine and triazine rings is non-planar. The repulsive interaction between the lone-pair electron is the reason for the rotation of the pyridine rings along the C-C bonds. The pyridine rings in the 2,4,6-tris(4-pyridyl)-1,3,5-triazine molecule are not coplanar with the central triazine ring. The arrangement of molecules in both crystals is mainly determined by the π-π intermolecular interactions. The X-ray geometry of both molecules in the solid-state is compared with the gas-phase geometry obtained by the ab initio molecular orbital calculations.

2,4,6-tris(2-pyridyl)-1,3,5-triazine

Molecules of the title compound, C18H12N6, were significantly distorted from planarity, with the three least-squares mean planes of the pyridine rings twisted from the plane of the central triazine ring by 15.7 (1), 33.8 (1) and 19.8 (1)°.

N-TYPE SEMICONDUCTOR, AND ORGANIC PHOTOELECTRIC DEVICE, IMAGE SENSOR, AND ELECTRONIC DEVICE INCLUDING THE SAME

Disclosed are an n-type semiconductor including compound represented by Chemical Formula 1 or Chemical Formula 2, an image sensor, and an electronic device. In Chemical Formula 1 and Chemical Formula 2, each substituent is as defined in the detailed description.

Novel synthesis of 2,4-bis(2-pyridyl)-5-(pyridyl)imidazoles and formation of N-(3-(pyridyl)imidazo[1,5-a]pyridine)picolinamidines: nitrogen-rich ligands

Heating a neat 1:2 mixture of 2-picolylamine and 2-cyanopyridine followed by treatment of the resultant red gummy substance with aqueous KOH resulted in the isolation of 2,4,5-tris(2-pyridyl)imidazole (1a) as the major product and N-(3-(2-pyridyl)imidazo[

Ruthenium complexes of easily accessible tridentate ligands based on the 2-aryl-4,6-bis(2-pyridyl)-s-triazine motif: Absorption spectra, luminescence properties, and redox behavior

A family of tridendate ligands 1a-e, based on the 2-aryl-4,6-di(2-pyridyl)- s-triazine motif, was prepared along with their hetero- and homoleptic Ru II complexes 2a-e ([Ru(tpy)(1a-e)]2+; tpy = 2,2′:6′,2″-ter-pyridine) and 3a-e ([(Ru(1a-e) 2]2+), respectively. The ligands and their complexes were characterized by 1H NMR spectroscopy, ES-MS, and elemental analysis. Single-crystal X-ray analysis of 2a and 2e demonstrated that the triazine core is nearly coplanar with the non-coordinating ring, with dihedral angles of 1.2 and 18.6°, respectively. The redox behavior and electronic absorption and luminescence properties (both at room temperature in liquid acetonitrile and at 77 K in butyronitrile rigid matrix) were investigated. Each species undergoes one oxidation process centered on the metal ion, and several (three for 2a-e and four for 3a-e) reduction processes centered on the ligand orbitals. All compounds exhibit intense absorption bands in the UV region, assigned to spin-allowed ligand-centered (LC) transitions, and moderately intense spin-allowed metal-to-ligand charge-transfer (MLCT) absorption bands in the visible region. The compounds exhibit relatively intense emissions, originating from triplet MLCT levels, both at 77 K and at room temperature. The incorporation of triazine rings and the near planarity of the noncoordinating ring increase the luminescence life-times of the complexes by lowering the energy of the 3MLCT state and creating a large energy gap to the dd state.

Novel cycloaddition of nitriles with monolithio- and dilithiobutadienes

Two novel and synthetically useful reaction patterns of organolithium compounds with nitriles are reported to afford pyridine derivatives as the final products. Both 1-lithio-1,3-dienes and 1,4-dilithio-1,3-dienes, which can be easily generated in situ by lithiation of their corresponding iodo compounds, react with nitriles in the presence of HMPA to form substituted pyridines including 2,2′-bipyridines and tetrahydroisoquinolines in high yields. Copyright

Lanthanide(III) Ion Catalyzed Reaction of Ammonia and Nitriles: Synthesis of 2,4,6-Trisubstituted-s-triazines

Lanthanum and yttrium trifluoromethanesulfonates at 1 mole percent concentration, have been found to catalyze a reaction between ammonia and aromatic nitriles to yield symmetrically substituted 2,4,6-triaryl-s-triazines.The generally high yields and relatively mild reaction conditions of this procedure suggest it as an alternative to other aromatic nitrile cyclotrimerization reactions.Of the aliphatic nitriles studied, acetonitrile and cyclopropanecarbonitrile gave good yields of triazine, propionitrile and butyronitrile gave significantly reduced yields of triazines 3b and3c respectively.Rearrangement of 3a and 3b to alkylated-4-aminopyrimidines was observed.