[ CAS No. 158014-74-5 ] {[proInfo.proName]}

Name: 158014-74-5|4-([2,2':6',2''-Terpyridin]-4'-yl)benzoic acid|97%
Brand: Ambeed
SKU: A198410
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2D 3D

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Quality Control of [ 158014-74-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 158014-74-5 ]

Product Details of [ 158014-74-5 ]

CAS No. :	158014-74-5	MDL No. :	MFCD22056799
Formula :	C₂₂H₁₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RPRRPKJKACRJDD-UHFFFAOYSA-N
M.W :	353.37	Pubchem ID :	15903886
Synonyms :

Calculated chemistry of [ 158014-74-5 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	103.09
TPSA :	75.97 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.95
Log Po/w (XLOGP3) :	3.11
Log Po/w (WLOGP) :	4.57
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	4.36
Consensus Log Po/w :	3.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-4.38
Solubility :	0.0146 mg/ml ; 0.0000413 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.37
Solubility :	0.0149 mg/ml ; 0.0000423 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-8.16
Solubility :	0.00000243 mg/ml ; 0.0000000069 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.61

Safety of [ 158014-74-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 158014-74-5 ]

* 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.

Upstream synthesis route of [ 158014-74-5 ]
Downstream synthetic route of [ 158014-74-5 ]

[ 158014-74-5 ] Synthesis Path-Upstream 1~8

1
[ 1122-62-9 ]
[ 1571-08-0 ]
[ 158014-74-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With ammonia; sodium hydroxide In ethanol; water at 20℃; for 17 h;	Round bottom flask 4-methoxycarbonyl benzaldehyde (1.0g, 6.1mmol) and 2-acetyl pyridine (1.37ml, 12.2mmol) were dissolved in 25ml of ethanol.Then 30percent NH₃were placed in a round flask, that the solution (1ml) and NaOH (0.488g, 12.2mmol) was dissolved in a minimal amount of water.Put the clear liquid solution of NaOH runners ttuieotgo is light yellow, and after about an hour and caught the red.In about 17 hours at room temperature, open the entrance to the round bottom flask and stirred haenotgo allow air to enter.Over time, the precipitate produced was more yellow.After the reaction was terminated, and then dissolved into water (50ml) and neutralized with HCl.The precipitate was filtered out and washed with water by filtration.And placed in 50ml of ethanol was refluxed for 1 hour and filtered and dried under vacuum (yield: 50percent).

Reference： [1] Patent: KR101489185, 2015, B1, . Location in patent: Paragraph 0268-0271
[2] Dalton Transactions, 2007, # 38, p. 4323 - 4332

2
[ 897037-23-9 ]
[ 158014-74-5 ]

Reference： [1] New Journal of Chemistry, 2018, vol. 42, # 11, p. 9317 - 9323
[2] Tetrahedron Letters, 2006, vol. 47, # 22, p. 3785 - 3789
[3] Chemical Communications, 2013, vol. 49, # 7, p. 731 - 733
[4] Chemistry Letters, 2008, vol. 37, # 4, p. 404 - 405

3
[ 1122-62-9 ]
[ 619-66-9 ]
[ 158014-74-5 ]

Reference： [1] Inorganic Chemistry, 2017, vol. 56, # 22, p. 13679 - 13696
[2] European Journal of Inorganic Chemistry, 2010, # 19, p. 3040 - 3050
[3] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19189 - 19198
[4] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 340, p. 170 - 180

4
[ 89972-77-0 ]
[ 158014-74-5 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 9, p. 995 - 998
[2] New Journal of Chemistry, 2015, vol. 39, # 9, p. 7403 - 7408

5
[ 1161783-92-1 ]
[ 158014-74-5 ]

Reference： [1] Journal of the American Chemical Society, 2009, vol. 131, # 29, p. 9874 - 9875

6
[ 625450-58-0 ]
[ 158014-74-5 ]

Reference： [1] Tetrahedron Letters, 2006, vol. 47, # 22, p. 3785 - 3789

7
[ 1122-62-9 ]
[ 158014-74-5 ]

Reference： [1] New Journal of Chemistry, 2018, vol. 42, # 11, p. 9317 - 9323

8
[ 1571-08-0 ]
[ 158014-74-5 ]

Reference： [1] New Journal of Chemistry, 2018, vol. 42, # 11, p. 9317 - 9323

[ 158014-74-5 ] Synthesis Path-Downstream 1~88

1
[ 897037-23-9 ]
[ 158014-74-5 ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 9317 - 9323
[2]Tetrahedron Letters,2006,vol. 47,p. 3785 - 3789
[3]Chemical Communications,2013,vol. 49,p. 731 - 733
[4]Chemistry Letters,2008,vol. 37,p. 404 - 405

2
[ 29022-11-5 ]
[ 71989-31-6 ]
[ 89972-78-1 ]
[ 158014-74-5 ]
FmocHNgly-CO-resin [ No CAS ]
Fmoc-val [ No CAS ]
C₇₂H₇₃N₁₇O₁₃ [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 2112 - 2114

3
[ 1122-62-9 ]
[ 1571-08-0 ]
[ 158014-74-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With ammonia; sodium hydroxide; In ethanol; water; at 20℃; for 17h;	Round bottom flask 4-methoxycarbonyl benzaldehyde (1.0g, 6.1mmol) and 2-acetyl pyridine (1.37ml, 12.2mmol) were dissolved in 25ml of ethanol.Then 30% NH3were placed in a round flask, that the solution (1ml) and NaOH (0.488g, 12.2mmol) was dissolved in a minimal amount of water.Put the clear liquid solution of NaOH runners ttuieotgo is light yellow, and after about an hour and caught the red.In about 17 hours at room temperature, open the entrance to the round bottom flask and stirred haenotgo allow air to enter.Over time, the precipitate produced was more yellow.After the reaction was terminated, and then dissolved into water (50ml) and neutralized with HCl.The precipitate was filtered out and washed with water by filtration.And placed in 50ml of ethanol was refluxed for 1 hour and filtered and dried under vacuum (yield: 50%).

Reference： [1]Patent: KR101489185,2015,B1 .Location in patent: Paragraph 0268-0271
[2]Dalton Transactions,2007,p. 4323 - 4332

4
[ 1571-08-0 ]
Et₂Zn [ No CAS ]
[ 158014-74-5 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3785 - 3789

5
[ 625450-58-0 ]
[ 158014-74-5 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3785 - 3789

Yield	Reaction Conditions	Operation in experiment
		Preparation Example 6 4-(2,2':6',2''-Terpyridin-4'-yl)benzoic acid (Compound 19) After 1.32 g of potassium permanganate was added to a mixture of 1.13 g of 4'-(4-methylphenyl)-2,2':6',2''-terpyridine obtained in Preparation Example 1, 9 ml of pyridine and 5 ml of water, the mixture was refluxed for 3 hours. Sodium hydrogensulfite was added to the reaction mixture to decompose unreacted potassium permanganate. Manganese dioxide was removed by suction with heating. The solvent was removed by distillation under reduced pressure and the residue was dissolved in 40 ml of ethanol and 10 ml of water with heating. To the solution was added 0.70 ml of 12 N hydrochloric acid aqueous solution. The crystals obtained were filtered by suction and thoroughly washed with water. The crude product was dissolved in a mixture of 10 ml of 1 N sodium hydroxide aqueous solution, 20 ml of water and 30 ml of ethanol. Insoluble matters were removed by spontaneous filtration. After 0.83 ml of 12 N hydrochloric acid aqueous solution was added to the filtrate, the crystals obtained were taken out by suction filtration. After washing successively with water and methanol, the crystals were dried in vacuum to give 0.68 g of the title compound. m.p. > 300C 1H NMR (CDCl3) delta (ppm): 7.30-7.40 (4H, m), 7.82-7.91 (4H, m), 8.66-8.76 (6H, m) MS (EI) 353 (M+)

7
ammonium hexafluorophosphate [ No CAS ]
[ 7719-09-7 ]
[Ru(2,2'-bipyridine)₂-dipyrido[3,2-a:2',3'-c]phenazine-7-amino][PF₆]₂ [ No CAS ]
[ 158014-74-5 ]
[Ru(2,2'-bipyridine)2(dppz-NHCO-Ph-tpy)][PF₆]2 [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 815 - 821

8
ammonium hexafluorophosphate [ No CAS ]
[ 7719-09-7 ]
[Ru(4,4'-diphenyl-2,2'-bipyridine)2(7-amino-dipyrido[3,2-a:2',3'-c]phenazine][PF₆]2 [ No CAS ]
[ 158014-74-5 ]
[Ru(4,4'-diphenyl-2,2'-bipyridine)2(dppz-NHCO-Ph-tpy)][PF₆]2 [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 815 - 821

9
ammonium hexafluorophosphate [ No CAS ]
[ 174476-77-8 ]
[ 158014-74-5 ]
Ru(N₃C₁₅H₁₀PO(OC₂H₅)2)(N₃C₁₅H₁₀C₆H₄COOH)⁽²⁺⁾*2PF₆^(1-)=(Ru(N₃C₁₅H₁₀PO(OC₂H₅)2)(N₃C₁₅H₁₀C₆H₄COOH))(PF₆)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 638 - 651

10
ammonium hexafluorophosphate [ No CAS ]
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
[ 158014-74-5 ]
[ 884588-82-3 ]

Reference： [1]Inorganica Chimica Acta,2006,vol. 359,p. 1666 - 1672

11
ruthenium(III) chloride trihydrate [ No CAS ]
[ 158014-74-5 ]
[Ru(4'-(4-carboxylphenyl)-2,2':6',2''-terpyridine^(1-))2]*1.25H₂O [ No CAS ]

Reference： [1]Dalton Transactions,2007,p. 4323 - 4332

12
[ 873216-50-3 ]
[ 158014-74-5 ]
[(4'-(p-carboxyphenyl)-2,2':6',2''-terpyridine)Ru(6-phenyl-2,4-di(2-pyridyl)-s-triazine)](PF₆)2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 10479 - 10488

13
ammonium hexafluorophosphate [ No CAS ]
dichlorobis(dimethyl sulfoxide)platinum(II) [ No CAS ]
[ 158014-74-5 ]
[PtCl(4'-(4-carboxyphenyl)-[2,2':6',2'']terpyridine)](hexafluorophosphate) [ No CAS ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 9653 - 9663

14
[ 1161783-92-1 ]
[ 158014-74-5 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9874 - 9875

15
ruthenium(III) chloride trihydrate [ No CAS ]
[ 158014-74-5 ]
[ 637740-33-1 ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2009,vol. 635,p. 2541 - 2549
[2]Polyhedron,2012,vol. 31,p. 227 - 234

16
[ 158014-74-5 ]
2,2':6',2''-terpyridine-Ph-COCl [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 2739 - 2741
[2]Physical Chemistry Chemical Physics,2015,vol. 17,p. 24166 - 24172

17
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7732-18-5 ]
[ 62-76-0 ]
[ 158014-74-5 ]
[Cd(4'-(4-carboxyphenyl)2,2':6',2''-terpyridine(-H))2(oxalate)]*2.5H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 715 - 719

18
aqueous cadmium chloride [ No CAS ]
[ 7732-18-5 ]
[ 158014-74-5 ]
[Cd(4'-(4-carboxyphenyl)2,2':6',2''-terpyridine(-H))2]*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 715 - 719

19
[ 7732-18-5 ]
[ 5743-04-4 ]
[ 158014-74-5 ]
[Cd(4'-(4-carboxyphenyl)2,2':6',2''-terpyridine(-H))2]*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 715 - 719

20
cadmium(II) perchlorate hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 158014-74-5 ]
[Cd(4'-(4-carboxyphenyl)2,2':6',2''-terpyridine(-H))2]*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 715 - 719

21
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7732-18-5 ]
[ 158014-74-5 ]
[Cd(4'-(4-carboxyphenyl)2,2':6',2''-terpyridine(-H))2]*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 715 - 719

22
ammonium hexafluorophosphate [ No CAS ]
ruthenium(III) chloride trihydrate [ No CAS ]
[ 158014-74-5 ]
[bis(4′-(4-carboxyphenyl)-terpyridine)ruthenium(II)](hexafluorophosphate)₂ [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2010,p. 3040 - 3050

23
[ 89972-77-0 ]
[ 158014-74-5 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 995 - 998
[2]New Journal of Chemistry,2015,vol. 39,p. 7403 - 7408

24
ammonium hexafluorophosphate [ No CAS ]
iridium(III) chloride hydrate [ No CAS ]
[ 107-21-1 ]
[ 178265-65-1 ]
[ 158014-74-5 ]
[Ir(4'-carboxyphenyl-2,2':6',2''-terpyridine)(4'-(4-aminophenyl)-2,2':6',2''-terpyridine)](PF₆)3 [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 2053 - 2061

25
[ 158014-74-5 ]
[ 1161783-92-1 ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 2093 - 2096

26
[ 158014-74-5 ]
4'-(4-carboxyphenyl)-2,2':6',2"-terpyridine dihydrochloride [ No CAS ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 2093 - 2096

27
[ 158014-74-5 ]
[ 1256557-04-6 ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 2093 - 2096

28
[ 158014-74-5 ]
[ 18107-18-1 ]
[ 897037-23-9 ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 2093 - 2096

29
dysprosium (III) nitrate * 4 water [ No CAS ]
[ 158014-74-5 ]
Dy(4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine)3 [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2011,vol. 14,p. 484 - 488

30
europium (III) nitrate * 4 water [ No CAS ]
[ 158014-74-5 ]
Eu(4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine)3 [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2011,vol. 14,p. 484 - 488

31
samarium (III) nitrate * 4 water [ No CAS ]
[ 158014-74-5 ]
Sm(4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine)3 [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2011,vol. 14,p. 484 - 488

32
terbium(III) nitrate tetrahydrate [ No CAS ]
[ 158014-74-5 ]
Tb(4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine)3 [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2011,vol. 14,p. 484 - 488

33
[ 1122-62-9 ]
[ 619-66-9 ]
[ 158014-74-5 ]

Reference： [1]Inorganic Chemistry,2017,vol. 56,p. 13679 - 13696
[2]European Journal of Inorganic Chemistry,2010,p. 3040 - 3050
[3]Dalton Transactions,2019,vol. 48,p. 17461 - 17471
[4]Journal of the American Chemical Society,2012,vol. 134,p. 19189 - 19198
[5]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 340,p. 170 - 180

34
[ 158014-74-5 ]
[ 1352132-21-8 ]

Reference： [1]Polyhedron,2012,vol. 31,p. 227 - 234

35
[ 158014-74-5 ]
[ 1352132-27-4 ]

Reference： [1]Polyhedron,2012,vol. 31,p. 227 - 234

36
holmium(III) nitrate hexahydrate [ No CAS ]
[ 6147-53-1 ]
[ 68-12-2 ]
[ 158014-74-5 ]
([Co₄Ho₂(4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine)4(CO₃)4(HCOO)2(H₂O)2]*2(N,N-dimethylformamide)*2H₂O)n [ No CAS ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 7433 - 7435

37
dysprosium(III) nitrate hexahydrate [ No CAS ]
[ 6147-53-1 ]
[ 68-12-2 ]
[ 158014-74-5 ]
([Co₄Dy₂(4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine)4(CO₃)4(HCOO)2(H₂O)2]*2(N,N-dimethylformamide)*5H₂O)n [ No CAS ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 7433 - 7435

38
[ 6147-53-1 ]
[ 158014-74-5 ]
[Co(4'-(4-carboxyphenyl)-2,2′:6',2"-terpyridine(-1H))₂]·5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine; In water; at 180℃; for 168h;pH 11;High pressure;	General procedure: A mixture of Ni(OAc)2·4H2O (0.031 g, 0.125 mmol), HL (0.088 g, 0.25 mmol) in deionized water (5 mL) was adjusted to pH=11.0 with triethylamine, and sealed in a 28 mL Teflon-lined stainless steel vessel, which was heated at 180 C for 7 day under autogenous pressure and thereafter cooled to room temperature. Brown block crystals of 2 were collected after washing with distilled water and dried in air (yield: 49%, based on Ni).

Reference： [1]Journal of Solid State Chemistry,2012,vol. 196,p. 398 - 403

39
zinc(II) acetate tetrahydrate [ No CAS ]
[ 158014-74-5 ]
[Zn(4'-(4-carboxyphenyl)-2,2′:6',2"-terpyridine(-1H))₂]_n·0.5nH₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With triethylamine; In water; at 180℃; for 168h;pH 11;High pressure;	General procedure: A mixture of Ni(OAc)2·4H2O (0.031 g, 0.125 mmol), HL (0.088 g, 0.25 mmol) in deionized water (5 mL) was adjusted to pH=11.0 with triethylamine, and sealed in a 28 mL Teflon-lined stainless steel vessel, which was heated at 180 C for 7 day under autogenous pressure and thereafter cooled to room temperature. Brown block crystals of 2 were collected after washing with distilled water and dried in air (yield: 49%, based on Ni).

Reference： [1]Journal of Solid State Chemistry,2012,vol. 196,p. 398 - 403

40
[ 6018-89-9 ]
[ 158014-74-5 ]
[Ni(4'-(4-carboxyphenyl)-2,2′:6',2"-terpyridine(-1H))₂]·5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With triethylamine; In water; at 180℃; for 168h;pH 11;High pressure;	A mixture of Ni(OAc)2·4H2O (0.031 g, 0.125 mmol), HL (0.088 g, 0.25 mmol) in deionized water (5 mL) was adjusted to pH=11.0 with triethylamine, and sealed in a 28 mL Teflon-lined stainless steel vessel, which was heated at 180 C for 7 day under autogenous pressure and thereafter cooled to room temperature. Brown block crystals of 2 were collected after washing with distilled water and dried in air (yield: 49%, based on Ni). Main IR absorption bands (KBr, cm-1): 3437.42(b), 1605.07(s), 1552.90(s), 1367.78(s), 786.42(s).

Reference： [1]Journal of Solid State Chemistry,2012,vol. 196,p. 398 - 403

41
[ 16454-60-7 ]
[ 158014-74-5 ]
[Nd(4'-(4-carboxyphenyl)-2,2′:6',2"-terpyridine(-1H))3]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	In water; at 180℃; for 144h;High pressure;	Compound 5 is hydrothermally synthesized by mixing 0.1 M Nd(NO3)3 solution (0.125 mmol, 1.25 mL). HL (1 mmol, 374 mg), and deionized water (8 mL) in a 28 mL Teflon-lined stainless steel vessel and heated at 180 C for 6 day and then cooled to room temperature. Light brown plate crystals of 5 were collected after washing with distilled water and dried in air (yield: 37%, based on Nd). Main IR absorption bands (cm-1): 3427.40(w), 1583.92(s), 1547.68(s), 1406.72(s), 817.83(b), 783.85(s).

Reference： [1]Journal of Solid State Chemistry,2012,vol. 196,p. 398 - 403

42
gadolinium(III) nitrate [ No CAS ]
[ 158014-74-5 ]
[Gd(4'-(4-carboxyphenyl)-2,2′:6',2"-terpyridine(-1H))3]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In water; at 180℃; for 144h;High pressure;	General procedure: Compound 5 is hydrothermally synthesized by mixing 0.1 M Nd(NO3)3 solution (0.125 mmol, 1.25 mL). HL (1 mmol, 374 mg), and deionized water (8 mL) in a 28 mL Teflon-lined stainless steel vessel and heated at 180 C for 6 day and then cooled to room temperature. Light brown plate crystals of 5 were collected after washing with distilled water and dried in air (yield: 37%, based on Nd).

Reference： [1]Journal of Solid State Chemistry,2012,vol. 196,p. 398 - 403

43
erbium(III) nitrate [ No CAS ]
[ 158014-74-5 ]
[Er(4'-(4-carboxyphenyl)-2,2′:6',2"-terpyridine(-1H))3]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	In water; at 180℃; for 144h;High pressure;	General procedure: Compound 5 is hydrothermally synthesized by mixing 0.1 M Nd(NO3)3 solution (0.125 mmol, 1.25 mL). HL (1 mmol, 374 mg), and deionized water (8 mL) in a 28 mL Teflon-lined stainless steel vessel and heated at 180 C for 6 day and then cooled to room temperature. Light brown plate crystals of 5 were collected after washing with distilled water and dried in air (yield: 37%, based on Nd).

Reference： [1]Journal of Solid State Chemistry,2012,vol. 196,p. 398 - 403

44
[ 158014-74-5 ]
C₃₂H₂₃Cl₂N₅ORu⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 19189 - 19198

45
[ 158014-74-5 ]
[ 1410795-07-1 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 19189 - 19198

46
[ 160262-16-8 ]
[ 158014-74-5 ]
[ 1380114-95-3 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 19189 - 19198

47
[ 68-12-2 ]
[ 7646-79-9 ]
[ 158014-74-5 ]
C₄₄H₃₀Cl₂CoN₆O₄*6C₃H₇NO [ No CAS ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 731 - 733

48
[ 7732-18-5 ]
[ 5970-45-6 ]
[ 158014-74-5 ]
Zn⁽²⁺⁾*2.5H₂O*2C₂₂H₁₄N₃O₂^(1-) [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 9954 - 9965

49
[ 7647-01-0 ]
[ 7732-18-5 ]
[ 5970-45-6 ]
[ 158014-74-5 ]
2Zn⁽²⁺⁾*2Cl^(1-)*0.5H₂O*2C₂₂H₁₄N₃O₂^(1-) [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 9954 - 9965

50
[ 244096-47-7 ]
[ 158014-74-5 ]
C₃₈H₃₉N₃O₁₄Si₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 17910 - 17913

51
terbium(III) nitrate hexahydrate [ No CAS ]
[ 557-34-6 ]
[ 158014-74-5 ]
TbZn(4′-(4-carboxyphenyl)-2,2′:6′,2″-terpyridine)(CO₃)2(H2O) [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 5266 - 5272

52
[ 1122-62-9 ]
[ 158014-74-5 ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 9317 - 9323

53
ammonium hexafluorophosphate [ No CAS ]
ruthenium(III) chloride trihydrate [ No CAS ]
[ 158014-74-5 ]
[bis(4′-(4-carboxyphenyl)-terpyridine)ruthenium(II)](hexafluorophosphate)₂ [ No CAS ]

Reference： [1]New Journal of Chemistry,2015,vol. 39,p. 7403 - 7408

54
cobalt(II) sulphate heptahydrate [ No CAS ]
4H₂O*6H₃N*6H⁽¹⁺⁾*7Mo^(6-)*24O^(2-) [ No CAS ]
[ 7732-18-5 ]
[ 68-12-2 ]
[ 158014-74-5 ]
[(CH₃)₂NH₂][Co(4-([4,2′:6′,4′′-terpyridin]-4′-yl)benzoic acid)(Mo₂O₇)]·2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	at 160℃; for 96.25h;Sealed tube;	The mixture of CoSO4·7H2O (0.2 mmol) or Ni(Ac)2·4H2O (0.2 mmol), Htpba (0.2 mmol), (NH4)6Mo7O24·4H2O (0.2 mmol), distilled water (9 mL) and DMF (1 ml) were stirred about 15 min in air, then transferred and sealed in a 17 mL Teflon-lined autoclave, which were heated at 160 C for 96 h under autogenous pressure. After the autoclave was cooled to room temperature at a rate of 10 C/h, purple block crystals of 1 and green block crystals of 2 were obtained, washed with distilled water several times, and dried at ambient temperature. We speculate that the DMF and/or (CH3)2NH may act as bases during the preparation procedures of 1 and 2. For compound 1, yield: 51% based on tpba. Elemental analysis (%) calcd for C24H26CoMo2N4O11: C, 36.15; H, 3.29; Co, 7.39; Mo, 24.07; N, 7.03%. Found: C, 36.24; H, 3.21; Co, 7.35; Mo, 24.12; N, 7.09%.

Reference： [1]Inorganic Chemistry Communications,2016,vol. 69,p. 52 - 56

55
4H₂O*6H₃N*6H⁽¹⁺⁾*7Mo^(6-)*24O^(2-) [ No CAS ]
[ 7732-18-5 ]
[ 6018-89-9 ]
[ 68-12-2 ]
[ 158014-74-5 ]
[(CH₃)₂NH₂][Ni(4-([4,2′:6′,4′′-terpyridin]-4′-yl)benzoic acid)(Mo₂O₇)]·2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	at 160℃; for 96.25h;Sealed tube;	The mixture of CoSO4·7H2O (0.2 mmol) or Ni(Ac)2·4H2O (0.2 mmol), Htpba (0.2 mmol), (NH4)6Mo7O24·4H2O (0.2 mmol), distilled water (9 mL) and DMF (1 ml) were stirred about 15 min in air, then transferred and sealed in a 17 mL Teflon-lined autoclave, which were heated at 160 C for 96 h under autogenous pressure. After the autoclave was cooled to room temperature at a rate of 10 C/h, purple block crystals of 1 and green block crystals of 2 were obtained, washed with distilled water several times, and dried at ambient temperature. We speculate that the DMF and/or (CH3)2NH may act as bases during the preparation procedures of 1 and 2. For compound 1, yield: 51% based on tpba. Elemental analysis (%) calcd for C24H26CoMo2N4O11: C, 36.15; H, 3.29; Co, 7.39; Mo, 24.07; N, 7.03%. Found: C, 36.24; H, 3.21; Co, 7.35; Mo, 24.12; N, 7.09%. For compound 2, yield: 55% based on tpba. Elemental analysis (%) calcd for C24H26NiMo2N4O11: C, 36.17; H, 3.29; Mo, 24.07; N, 7.03; Ni, 7.36%. Found: C, 36.22; H, 3.25; Mo, 24.11; N, 7.12; Ni, 7.31%.

Reference： [1]Inorganic Chemistry Communications,2016,vol. 69,p. 52 - 56

56
[ 778612-41-2 ]
europioum(III) chloride [ No CAS ]
[ 158014-74-5 ]
Eu³⁺-[P2-NA]₃(4-(4-carboxyphenyl)-2,2':6',2"-terpyridine) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Shrink flask 4-(4-(4-methoxyphenyl)naphthalene-1-yl)benzoic acid (0.1g, 0.28mmol) was dissolved in the potassium hydride (0.0111g, 0.28mmol), 100ml of purified THF (complex substance since the operation in the glove box was sensitive to moisture).For 24 hours at room temperature, H2 and stirred until the gas is not ejected. After naphthalene salt is made, europium chloride (Europiumchloride, 0.024g, 0.1mmol) and 4- (4-carboxyphenyl) 2,2':6', 2"-terpyridine (0.0353g, 0.1mmol) to a flask into a dissolved in methanol.And dissolved using the minimum amount of methanol, the salt is made into a flask naphthalene was stirred at room temperature for 48 hours.After completion of the reaction was filtered and the filtrate was dried under a reduced pressure.Finally, To give a Eu3+-[P2-NA]3(NL2) white solid washed with hexane and ether.

Reference： [1]Patent: KR101489185,2015,B1 .Location in patent: Paragraph 0351-0354; 0363-0366

57
[ 4282-31-9 ]
aqueous cadmium chloride [ No CAS ]
[ 7732-18-5 ]
[ 158014-74-5 ]
[Cd₂(4'-(4-carboxylphenyl)-2,2:6,2"-terpyridinate)₂(thiophene-2,5-dicarboxylate)]·3.5H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.2%	at 160℃; for 72h;High pressure; Autoclave;	General procedure: A mixture of CdCl2·2.5H2O (24.0mg, 0.10mmol), Hcpt (18.3mg, 0.05mmol), H2tpd (12.1mg, 0.05mmol), H2O (10mL) was sealed in a 23-mL Teflon-lined stainless steel Parr acid digestion bomb, heated at 160C for 72h, and then allowed to cool to room temperature for 60h. Brown rod-shaped crystals of 1 were isolated on a filter and washed with deionized water and ethanol, and dried in air. Yield 27.2% (15.8mg, 0.0136mmol, based on CdII). Elem. Anal. (%) Calcd. for Cd2C50H37N6O11.5S: C, 51.65; H, 3.21; N, 7.23. Found: C, 51.11; H, 3.09; N, 7.32.

Reference： [1]Journal of Solid State Chemistry,2015,vol. 221,p. 345 - 350

58
[ 4282-31-9 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 7732-18-5 ]
[ 158014-74-5 ]
[Mn₂(4'-(4-carboxylphenyl)-2,2:6,2"-terpyridinate)₂(thiophene-2,5-dicarboxylate)]·3.5H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 160℃; for 72h;High pressure; Autoclave;	General procedure: Compound 2 was synthesized under similar reaction conditions using the same molar ratios of reactants, except that MnCl2·4H2O (21.7mg, 0.10mmol) was used instead of CdCl2·2.5H2O. Red rod-shaped crystals of 2 were isolated on a filter and washed with deionized water and ethanol, and dried in air. Elem. Anal. (%) Calcd. for Mn2C50H35.5N6O10.75S: C, 58.06; H, 3.46; N, 8.13. Found: C, 58.10; H, 3.43; N, 8.22.

Reference： [1]Journal of Solid State Chemistry,2015,vol. 221,p. 345 - 350

59
aqueous cadmium chloride [ No CAS ]
[ 7732-18-5 ]
[ 158014-74-5 ]
[CdCl(4'-(4-carboxylphenyl)-2,2:6,2"-terpyridinate)]·3.75H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	at 160℃; for 72h;High pressure; Autoclave;	General procedure: Compound 3 was synthesized under similar reaction conditions using the same molar ratios of reactants for 1, except that H2tpd ligand was not added. Yellowish-brown rod-shaped crystals of 3 were isolated on a filter and washed with deionized water and ethanol, and dried in air. Yield 26% (7.1mg, 0.013mmol, based on the Hcpt ligand). Elem. Anal. (%) Calcd. for CdC22H21.5N3O5.75Cl: C, 47.67; H, 3.82; N 7.58. Found: C, 47.53; H, 3.43; N, 7.53.

Reference： [1]Journal of Solid State Chemistry,2015,vol. 221,p. 345 - 350

60
[ 158014-74-5 ]
4′-(N,N′-diphenylbenzamidine)-2,2’:6’,2’’-terpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 17850 - 17858

61
[ 158014-74-5 ]
[Ru{4′-(N,N′-dipropylbenzamidine)-2,2’:6’,2’’-terpyridine}(2,2’:6’,2’’-terpyridine)](PF₆)₂ [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 17850 - 17858

62
[ 158014-74-5 ]
[Ru{4′-(N,N′-diphenylbenzamidine)-2,2’:6’,2’’-terpyridine}(2,2’:6’,2’’-terpyridine)](PF₆)₂ [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 17850 - 17858

63
[ 158014-74-5 ]
4′-(N,N′-dipropylbenzamidine)-2,2’:6’,2’’-terpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 17850 - 17858

64
[ 107-10-8 ]
[ 158014-74-5 ]
4′-(4-N-propylbenzamide)-2,2’:6’,2’’-terpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 17850 - 17858

65
[ 62-53-3 ]
[ 158014-74-5 ]
4′-(N-phenylbenzamide)-2,2’:6’,2’’-terpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 17850 - 17858

66
C₆₃H₄₃Cl₃N₉Ru₂ [ No CAS ]
potassium nitrate [ No CAS ]
[ 158014-74-5 ]
C₈₅H₅₈N₁₂O₂Ru₂⁽⁴⁺⁾*4HNO₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		RuCl33H2O (5.52 mmol, 1.145 g) and L1 (1.657 mmol, 0.896 g)were dissolved in 70 mL of a miscellaneous solvent of chloroformand C2H5OH (1/3, v/v). This mixture was refluxed for 5 h and thencondensed to 12 mL. The dark brown precipitate wasfiltered,washed with C2H5OH, and dried in vacuo. The solid collected wasdissolved in acetonitrile and purified by column chromatographyusing alumina. Yield 16.3%. 1 equivalent of [Ru(L1)Ru]2Cl3 wasreacted with 1.0 equivalent of L2 were dissolved in 60 mL of amiscellaneous solvent of chloroform and C2H5OH (1/3, v/v). Thismixture was refluxed for 5 h and then condensed to 15 mL. Thedark brown precipitate wasfiltered, washed with C2H5OH, anddried in vacuo followed by purification using column chromatog-raphy in alumina adsorbent. Further 1 equivalent of [Ru(L1)Ru(L2)]Cl3 was reacted with 1 equivalent of 4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine (L4) with a few drops of triethyl amminein 20 mL of refluxing ethanol for 5 h. A alumina column was usedfor the purification (CH3CN, H2O and saturated KNO3 used as theeluent). The metal complex was collected as the solution of nitratesalt, concentrated and then 1 small spatula of KPF6 was added. Thered precipitate was then collected in a medium frit and washed with water and diethyl ether.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 340,p. 170 - 180

67
C₅₉H₄₃Cl₃N₉O₂Ru₂ [ No CAS ]
potassium nitrate [ No CAS ]
[ 158014-74-5 ]
C₈₁H₅₈N₁₂O₄Ru₂⁽⁴⁺⁾*4HNO₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		RuCl33H2O (5.52 mmol, 1.145 g) and L1 (1.657 mmol, 0.896 g)were dissolved in 70 mL of a miscellaneous solvent of chloroformand C2H5OH (1/3, v/v). This mixture was refluxed for 5 h and thencondensed to 12 mL. The dark brown precipitate wasfiltered,washed with C2H5OH, and dried in vacuo. The solid collected wasdissolved in acetonitrile and purified by column chromatographyusing alumina. Yield 16.3%. 1 equivalent of [Ru(L1)Ru]2Cl3 wasreacted with 1.0 equivalent of L2 were dissolved in 60 mL of amiscellaneous solvent of chloroform and C2H5OH (1/3, v/v). Thismixture was refluxed for 5 h and then condensed to 15 mL. Thedark brown precipitate wasfiltered, washed with C2H5OH, anddried in vacuo followed by purification using column chromatog-raphy in alumina adsorbent. Further 1 equivalent of [Ru(L1)Ru(L2)]Cl3 was reacted with 1 equivalent of 4'-(4-carboxyphenyl)-2,2':6',2''-terpyridine (L4) with a few drops of triethyl amminein 20 mL of refluxing ethanol for 5 h. A alumina column was usedfor the purification (CH3CN, H2O and saturated KNO3 used as theeluent). The metal complex was collected as the solution of nitratesalt, concentrated and then 1 small spatula of KPF6 was added. Thered precipitate was then collected in a medium frit and washed with water and diethyl ether.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 340,p. 170 - 180

68
[ 7647-01-0 ]
europium(III) nitrate hexahydrate [ No CAS ]
[ 543-90-8 ]
[ 158014-74-5 ]
C₂₂H₁₄N₃O₂^(1-)*C₂H₃O₂^(1-)*Cl^(1-)*Eu⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In water; N,N-dimethyl-formamide; at 20 - 160℃; for 96.5h;Sealed tube;	A mixture of Cd(CH3COO)2 (0.1mmol, 26.6mg), Eu(NO3)3·6H2O (0.1mmol, 44.6mg) and HL (0.1mmol, 35.3mg) was dissolved in 1.0mL distilled water, 4.0mL dimethylformamide (DMF) and 2.0mL HCl (0.1molL-1). After stirring for half-hour at room temperature, the mixture was sealed in a 23mL Teflon-lined stainless steel vessel, which was heated at 160C for 96h and then slowly cooled to room temperature at a rate of 5Ch-1. The yellow rhombic block-shaped crystals were collected, which were filtered off and washed with DMF several times to give 1. Yield 56% (based on HL). Anal. Calc. for C24H17ClN3O4Eu: C, 48.10; H, 2.86; N, 7.01%; Found: C, 48.20; H, 2.88; N, 7.02%. IR (KBr, cm-1): 3423(s), 1605(s), 1551(m), 1478(m), 1395(s), 1248(m), 1164(s), 1013(w), 864(m), 783(s)

Reference： [1]Journal of Solid State Chemistry,2018,vol. 258,p. 86 - 92

69
[ 10196-18-6 ]
[ 158014-74-5 ]
[Zn(tpb)2(Htpb)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid; In water; N,N-dimethyl-formamide; at 140℃; for 72h;Autoclave;	a) in the following molar ratio of raw materials weighed, Htpb: Zn (NO3)2DMFH2O: HNO3A molar ratio of 1: 2: 516: 8888: 18, as 50mL glass beaker and stirred for 0.5 hours mixing;b) step a) the resulting mixture was transferred into a 25mL autoclave, reacted at 140 3 days;c) cooled to room temperature, the yellow crystals was observed, filtered, washed with of DMF, washed with water, naturally dried to give the desired product.Using Perkin-Elmer2400 Elemental Analyzer C of the target product, H, N elemental elemental analysis, Calcd. (%): C, 71.93; H, 4.02; N, 11.18; actually measured (%): C, 71.87; H, 4.03; N, 11.21.Use Nicolet Impact 410FTIR spectrometer in KBr as the substrate, the 400-4000 cm-1infrared analysis of the range of the target product, the FT-the IR (KBr, cm & lt-1): 3047 (m), 2964 (W), 1632 ( m), 1609 (vs), 1494 (m), 1398 (vs), 1245 (s), 1221 (s), 1121 (m), 889 (m), 836 (m).The target product X- ray diffraction analysis, the crystal structure shown in Figure 2, each of the target product using zinc ion hexacoordination embodiment, a zinc ion and two TPB-nitrogen atom of the pyridine group chelation.Target product at 365nm ultraviolet light, a yellow phosphor, shown in Figure 3.Using the target type Shimadzu XRD-6100 X- ray diffraction powder diffraction target product testing, resulting X- ray powder diffraction pattern with pattern matching by high mercury software simulation results shown in Figure 5, the conditions of preparation of the present higher purity of product samples.Repeatedly embodiment of the present embodiment, the resulting zinc complex [Zn (tpb)2(Htpb)2] Mass of 6.7 ~ 7.6mg, yield calculated Htpb, i.e. depending on the reaction was Htpb with [Zn (tpb)2(Htpb)2The molar ratio], derived [Zn (tpb)2(Htpb)2] The theoretical mass, zinc complex [Zn (tpb)2(Htpb)2] The actual quality of the theoretical yield is the ratio of the mass yield of 60.1% ~ 69.0%.

Reference： [1]Patent: CN106854175,2017,A .Location in patent: Paragraph 0029-0038; 0039-0050

70
Europium nitrate hexahydrate [ No CAS ]
[ 557-34-6 ]
[ 158014-74-5 ]
C₂₂H₁₄N₃O₂^(1-)*2CO₃^(2-)*H₂O*Zn⁽²⁺⁾*Eu⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A mixture of HL (0.2 mmol, 70.2 mg), Ln(NO3)2·6H2O (Ln = Eu (1), Gd (2), Dy (3), Ho (4), Er (5), Tm (6), Yb (7), Lu (8)) (0.1 mmol), Zn(CH3COO)2 (0.2 mmol, 44.2 mg), and 8 mL of DMF/water (6:2) solutions were stirred for 30 mins at room temperature and were sealed in a 23 mL Teflon-lined stainless steel vessel, which was heated at 160 C for 4 days and then slowly cooled to room temperature at a rate of 2 C h-1. The yellow needle shaped crystal was isolated by filtration and washed with H2O several times, yield 50-60%. For 1: IR (KBr pellet, cm-1): 3517.04(s), 1633.98(s), 1584.08(m), 1448.49(m), 1321.62(s), 1259.93(m), 1215.89(s), 1128.95(w), 994.35(m), 829.00(m), 766.92(s); Anal. Calc. for C24H16EuN3O9Zn: C, 40.69; H, 2.26; O, 20.22; N, 5.93%. Found: C, 40.70 H, 2.25; O, 20.20; N, 5.94%.