Benzoic acid, 4,4',4''-(1,3,5-triazine-2,4,6-triyl)tris-

• CAS: 61414-16-2
• Catalog Number: ACM61414162
• Category: Main Products
• Molecular Weight: 441.39
• Molecular Formula: C24H15N3O6
• Appearance: Brown solid

Case Study

2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine as an Electron-Accepting Monomer for Blue-Emitting Hyperbranched Polyamides

Hu, Xiaobing, et al. Journal of Polymer Research 25.3 (2018): 67.

2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine (H3TATB) functions as a trifunctional electron-accepting monomer whose one-pot polycondensation with p-phenylenediamine builds donor-acceptor hyperbranched polyamides for blue light-emitting devices and ferric ion sensing.
Experimental Protocol: H3TATB and p-phenylenediamine are condensed in N-methylpyrrolidone containing pyridine and triphenyl phosphite under argon at 130°C for 5 h, using diamine-to-triazine feed ratios of 1:1 and 2:1 to produce carboxyl- and amino-terminated polymers, which are extracted with deionized water and dried at 90°C under reduced pressure. Fluorescence quantum yields are measured in DMSO against quinine sulfate, and metal ion responses are recorded at an excitation wavelength of 390 nm.
Performance Evaluation: The polymers emit strong blue light at 457 nm and 476 nm with quantum yields of 41% and 8%, Stokes shifts of 57 nm and 76 nm, and number-average molecular weights of 6723 and 7019 g/mol. Density functional theory reveals effective separation of the highest occupied and lowest unoccupied molecular orbitals on donor and acceptor units, favoring intramolecular charge transfer. Addition of ferric ions markedly quenches the fluorescence, with a red-shift of the emission maximum for the carboxyl-terminated polymer, demonstrating selective Fe³⁺ detection among thirteen competing metal ions.

2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine as a Sensitizing Ligand for Ratiometric Luminescence Thermometry

Wang, Hongwei, et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 244 (2021): 118781.

2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine (TCTZ) acts as a C3-symmetric bridging ligand whose coordination to terbium and europium ions creates luminescent metal-organic complexes for non-contact ratiometric temperature sensing.
Experimental Protocol: TCTZ is dissolved in a 4:1 mixture of dimethylformamide and deionized water, combined with lanthanide nitrate solutions, adjusted to pH 5-6 with dilute sodium hydroxide, and heated in a sealed autoclave at 160°C for 48 h to afford Tb1-xEux-TCTZ(DMF) dihydrate complexes with x = 0, 0.01 and 1. Temperature-dependent photoluminescence and lifetime measurements are recorded over 303-403 K.
Performance Evaluation: Excitation of the ligand at 340 nm sensitizes intense green emission of terbium at 543 nm and red emission of europium at 615 nm, and the europium complex shows an absolute quantum yield of 49%. Tb-TCTZ reaches a maximum relative sensitivity of 5.36% K^-1 at 403 K with a temperature resolution below 0.05 K, while the mixed Tb_0.99Eu_0.01-TCTZ attains absolute and relative sensitivities of 5.16% and 3.22% K^-1. For Tb-TCTZ, lifetime-based readout provides a relative sensitivity of 1.69% K^-1 at 403 K. The emission color shifts from green at 303 K to red at 403 K, enabling colorimetric visualization, with a repeatability value of 0.998.

2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine as an Organic Linker for Photocatalytic Hydrogen Evolution

Zhang, Ruoqian, et al. Journal of Solid State Chemistry 271 (2019): 260-265.

2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine (H3TATB) serves as the photoactive organic linker whose assembly with cobalt secondary building units constructs the triazine-based metal-organic framework PCN-9(Co), a photocatalyst for hydrogen evolution from water.
Experimental Protocol: H3TATB (0.2 g), cobalt(II) nitrate hexahydrate and tetrafluoroboric acid are dissolved in dimethyl sulfoxide with dimethylformamide, stirred for 30 min, and solvothermally treated at 135°C for 72 h to yield violet crystals. The activated framework is then immersed in aqueous chloroplatinic acid solutions of 0.386-1.930 mM for 20 h at room temperature to give the platinum-modified PCN-9-Pt. Photocatalytic tests suspend 20 mg of catalyst in 20 mL water containing 1 mL triethanolamine at 10°C under irradiation from a 300 W xenon lamp.
Performance Evaluation: PCN-9(Co) evolves hydrogen at 4.8 micromol per gram per hour, slightly above the free ligand at 4.0, while PCN-9-Pt reaches 33.5, a 6.8-fold enhancement. X-ray photoelectron spectroscopy confirms platinum(IV) coordination to triazine nitrogen, and photoluminescence and electrochemical impedance results indicate improved charge-carrier separation and reduced transfer resistance, rationalizing the superior photocatalytic activity. The best activity corresponds to a Pt/Co atomic ratio of 0.61, and blocking nitrogen coordination by acid pretreatment reverts activity to that of the unmodified framework, confirming that platinum binds the triazine nitrogen; platinum remains in the +4 state after reaction, indicating stability.

Custom Q&A

What is the molecular formula of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The molecular formula is C24H15N3O6.

What is the molecular weight of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The molecular weight is 441.4 g/mol.

What is the IUPAC name of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The IUPAC name is 4-[4,6-bis(4-carboxyphenyl)-1,3,5-triazin-2-yl]benzoic acid.

What is the InChI of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The InChI is InChI=1S/C24H15N3O6/c28-22(29)16-7-1-13(2-8-16)19-25-20(14-3-9-17(10-4-14)23(30)31)27-21(26-19)15-5-11-18(12-6-15)24(32)33/h1-12H,(H,28,29)(H,30,31)(H,32,33).

What is the InChIKey of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The InChIKey is MSFXUHUYNSYIDR-UHFFFAOYSA-N.

What is the canonical SMILES of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The canonical SMILES is C1=CC(=CC=C1C2=NC(=NC(=N2)C3=CC=C(C=C3)C(=O)O)C4=CC=C(C=C4)C(=O)O).

What is the CAS number of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The CAS number is 61414-16-2.

What is the European Community (EC) Number of 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine?

The European Community (EC) Number is 689-419-3.

Is 2,4,6-Tris(4-carboxyphenyl)-1,3,5-triazine a covalently-bonded unit?

Yes, it is a covalently-bonded unit.

Synthetic Use

Upstream Synthesis Route 1

• 6726-45-0

• 61414-16-2

Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 3896 - 3897