Triazine Moiety Research Articles

Engineering iodine decorated azo-bridged porous organic polymer: A brilliant catalyst for the preparation of 2,4,6-trisubstituted pyridines

Iodine catalysis in organic transformations affords detailed coverage of recent advances in iodine chemistry. In this direction, the azo-bridged porous organic polymer bearing triazine and phloroglucinol moieties (Azo-POP1) was constructed via interfacial azo-coupling polymerization in water at room temperature. Considering its high specific surface area (153 m2.g-1) and pore size of 2.2 nm, karyotype-like morphology and considerable surface wettability, Azo-POP1 was successfully used as an adsorbent of I2. The adsorption kinetics studies show that the adsorption reaches equilibrium within one hour and increases with temperature. To our delight, this system (I2@Azo-POP1) was used as an irreplaceable heterogeneous catalyst for the synthesis of 2,4,6-trisubstituted pyridines via condensation reaction of diverse ketones with benzylamine and the following cyclization and cooperative vinylogous anomeric based oxidation. All the products were prepared in good yields under mild reaction conditions. Also, this attitude benefits from the environmentally friendly and recyclability of described catalyst.

Boosting photocatalytic nitrogen fixation performance by adjusting the intramolecular D-A structure and band gap of thiophene-based COFs

Herein, we successfully synthesized two photoactive donor–acceptor (D-A) covalent organic frameworks by incorporating electric-deficient triazine and electric-rich benzotrithiophene moieties into the framework. The introduction of sulfur atom and triazine unit significantly change the intrinsic band gap of JLNU-COFs, this leads to an expanded range of light absorption, encompassing wavelengths from ultraviolet to visible. The narrow band gap of JLNU-311 allows for efficient utilization of visible light while maintaining the thermodynamic activity required for nitrogen reduction within appropriate energy bands. JLNU-311 modified with strong electron absorbing groups has higher activity to NH3 production without co-catalyst or sacrificial agent, and yield can reach 325.6 µmol/g/h. Theoretical calculation further confirm that acceptor structure can effectively regulate the band gap width, promote the adsorption, dissociation and protonation of N2 molecules on JLNU-COFs, and thus reduce the energy barrier of photocatalytic nitrogen reduction reaction (PNRR). Therefore, this study provides an effective strategy for design of active nitrogen fixing photocatalysts.

A Pharmacological Overview and Recent Patent of Triazine Scaffold in Drug Development: A Review

<p>The triazine moiety holds a special and very important position in the field of medicinal chemistry owing to its enormous biological and pharmacological potential. Over eras, triazine scaffolds have been investigated for synthesizing novel molecules that may be used for the treatment of different types of pathological conditions, such as infections, cancer, inflammation etc. A vast number of lead molecules have been established from the triazine moiety. The triazine fused with numerous heterocyclic rings, such as pyrrole, benzimidazole, indole, imidazole, carbazole, etc., have formed various bicyclic with pharmacological actions. The triazines display a wide range of activities, and synthesizing various marketable medicines that hold triazine moiety has made the attention of chemists worldwide grow over the years in the moiety. In this review article, the commercially available compound containing triazine has been presented, and an attempt has been made to collect the works reported, mostly in the past decade, by numerous scientists, related to the structural differences amongst the triazine analogues giving antitumor, and antimicrobial and other activities. </p><p> The objective of this review article was to outline the current information on triazines and their derivatives with respect to their biological potential and various pharmacological activities. </p><p> The summary of this review article would be helpful and describe the function and activity of the moiety to bring up-to-date the scientists working in the direction of designing and synthesising novel lead molecules for the treatment of different types of disease with the current molecules that have been synthesized from the triazine scaffold.</p>

The impact of DOPO‐derived phosphoramides containing triazine moieties on the flame retardancy and smoke suppression properties of waterborne polyurethane

AbstractWaterborne polyurethane (WPU), which is a novel and environmentally friendly variety of polyurethane, replaces organic solvents with water. It has been extensively utilized in diverse fields encompassing coatings, textile finishing, building decoration, adhesives, plastic chemistry, and others. However, WPU is inherently flammable and releases a significant amount of smoke production during the combustion process. This research presents an original fire‐resistant Waterborne Polyurethane (WPU) with a newly‐integrated flame‐retardant component comprising a triazine phosphoramidate segment derived from 9,10‐dihydro‐9‐oxo‐10‐phosphaphenanthrene‐10‐oxide (DOPO) within its primary structure. In comparison to pure WPU, the limiting oxygen index (LOI) of flame‐retardant WPU (FRWPU) increased from 19.6% to 29.2%. In UL‐94 testing, the FRWPU film achieved a V‐0 rating with only 6% retarding component. Additionally, in cone calorimetry tests, Total Heat Release (THR), peak Heat Release Rate (pHRR), Total Smoke Production (TSP), Smoke Production Rate (SPR), and peak Carbon Monoxide Production Rate (pCOP) are decreased by 27.7%, 16.2%, 64.6%, 61.3%, and 77.8%, respectively. The greater degree of graphitization observed in the residual carbon substantially impeded heat exchange and the emission of smoke during combustion. Flame‐retardant intermediate segments greatly improved the FRWPUs' ability to suppress smoke and remain flame‐retardant. The creation and formulation of aqueous polyurethanes that are flame‐retardant can benefit greatly from the insights and references offered by this research.

Polymerization-induced emission and selective detection to Fe3+/ Fe2+ of triazine-containing polyureas

In this study, four polyureas with triazine moiety (PUAs) were successfully synthesized through the polymerization of triazine-containing diamine and diisocyanate. The intramolecular aggregation of triazine rings and urea groups along the macromolecular backbone gives PUAs a significant polymerization-induced emission (PIE). Among the four PUAs, PUA-LP shows a significant fluorescent emission at 450 nm, compared to non/weak fluorescent 2,4-diamino-6-phenyl-1,3,5-triazine and L-Lysine diisocyanate ethyl ester monomers. Additionally, the external factors such as solution concentration, excitation wavelength, and precipitants also play a crucial role in the fluorescence of PUAs. As expected, PUA-LP can selectively recognize and detect Fe3+/Fe2+ ions even in the presence of 12 other metal ions and 10 anions. The limit of detection of PUA-LP to Fe3+/Fe2+ is as low as 1.02 μM (0.06 mg/L) and 0.86 μM (0.05 mg/L), respectively, and far below 0.3 mg/L of the allowable national standard for drinking water by WHO. Furthermore, the quenching mechanism of Fe3+/Fe2+ to PUA-LP is attributed to static quenching caused by the coordination of Fe3+/Fe2+ ions with a coordination ratio of 2:1. Based on PIE, the fluorescent PUA-LP was made into an observable and portable testing paper for detecting Fe3+/Fe2+ ions. Finally, we measured the recovery rate of the actual tap water samples and compared the performance of PIE-active PUA-LP with the other reported fluorescent probes to Fe3+/Fe2+ ions.

The activity of pyrazolo[4,3-e][1,2,4]triazine and pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine sulphonamide derivatives in monolayer and spheroid breast cancer cell cultures

In the last decade, an increasing interest in compounds containing pyrazolo[4,3-e][1,2,4]triazine moiety is observed. Therefore, the aim of the research was to synthesise a novel sulphonyl pyrazolo[4,3-e][1,2,4]triazines (2a, 2b) and pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine sulphonamide derivatives (3a, 3b) to assess their anticancer activity. The MTT assay showed that 2a, 2b, 3a, 3b have stronger cytotoxic activity than cisplatin in both breast cancer cells (MCF-7 and MDA-MB-231) and exhibited weaker effect on normal breast cells (MCF-10A). The obtained results showed that the most active compound 3b increased apoptosis via caspase 9, caspase 8, and caspase 3/7. It is worth to note that compound 3b suppressed NF-κB expression and promoted p53, Bax, and ROS which play important role in activation of apoptosis. Moreover, our results confirmed that compound 3b triggers autophagy through increased formation of autophagosomes, expression of beclin-1 and mTOR inhibition. Thus, our study defines a possible mechanism underlying 3b-induced anti-cancer activity against breast cancer cell lines.

Synthesis, spectroscopic, biological and structural characterizations for the gold(III), platinum(IV), and Ruthenium(III) ceftriaxone drug complexes

Three new metal complexes of ceftriaxone (cef), incorporating platinum(IV), gold(III), and ruthenium(III), were prepared. The complexes were prepared using a 1:2 molar ratio between ceftriaxone sodium salt (Na2cef) to AuCl3, PtCl4, and RuCl3 salts in methanol solvent. The as-synthesized complexes were characterized using microanalytical techniques for C, H, N, and S elements, magnetic and molar conductance measurements, as well as spectroscopic methods including FTIR, 1H NMR, and UV-Vis. The shape, morphology and size calculations have been examined using SEM, TEM, and X-ray diffraction data. The cef complexes were six-coordinate systems possessing a distorted octahedral geometry. Through the oxygen of both triazine and carboxylate moieties with the chemical formulae [Au(cef)2(Cl)(H2O)] (I), [Pt(cef)2(Cl)2] (II), and [Ru(cef)2(Cl)(H2O)] (III) the antibiotic cef acts as a bidentate ligand towards three metal ions. The newly created complexes demonstrated antibacterial activity showing efficacy in comparison to the cef sodium ligands. In vitro, antibacterial assays against specific microorganisms were evaluated to assess the antibacterial activities of the complexes. Cytotoxicity assays for cef complexes were conducted for HepG-2 and MCF-7 cell lines, representing human hepatocellular carcinoma and breast cancer, respectively. A value of 22.4 g and 26.2 g for 50% inhibitory concentration (IC50), respectively, for HepG-2 and MCF-7 were obtained for [Ru(cef)2(Cl)(H2O)] (III). KEY WORDS: Ceftriaxone sodium, Gold, Ruthenium, Platinum, Complexes, FTIR, IC50 Bull. Chem. Soc. Ethiop. 2024, 38(4), 937-948. DOI: https://dx.doi.org/10.4314/bcse.v38i4.10

Synthesis and Electrical Properties of a New Bipolar Material Using Spacer Moiety

To develop a deep-blue emitter, a molecule with bipolar characteristics was designed as a donor-spacer-acceptor type, in which 9-(4-(4,6-diphenyl-1),3,5-triazin-2-yl)-2,5-dimethylphenyl)-9H-carbazole (DTPCZ)—with carbazole as an electron donating group and a diphenyl triazine moiety as an electron accepting group—was successfully synthesized. The photoluminescence (PL) maxima of DTPCZ were 421 nm in the solution state and 425 nm in the film state, indicating emission in the deep-blue region. DTPCZ also exhibited high thermal stability, with a degradation temperature of 349 °C. To confirm the electroluminescence (EL) characteristics, DTPCZ was applied as a dopant at 10, 20, and 30 wt% in a blue-fluorescent organic light-emitting diode (OLED) device. The highest efficiency was achieved using the 20 wt% doped device, with a current efficiency of 1.2 cd/A, an external quantum efficiency of 2.3%, and a Commission Internationale de l’Eclairage proceedings y-value of 0.06. Thus, deep-blue emission could be realized in the film state. These molecular design strategies can be applied to various fields, such as organic semiconductors.

Triazine-containing porous organic polymers from Diels-Alder reactions for efficient molecular adsorption and photocatalytic degradation

As a reversible and simple synthetic strategy, Diels-Alder (DA) reactions were recently exploited for the construction of porous organic polymers (POPs) with diverse structures and functions, which hold the promise to synthesize functional POPs in large scale. However, these methods typically need high polymerization temperature, and the structural diversity is limited for their practical applications. In this work, a series of DA-POPs were successfully synthesized via the Diels-Alder reactions of furan- and alkynyl-functionalized monomers. To reduce the activation energy of the reaction, we introduced 1,3,5-triazine moiety to alkynyl-functionalized monomers, which substantially lowered the polymerization temperature to 120 °C. Leveraging the reported photoelectric activity from triazine moiety, we applied these POPs materials to the adsorption and photocatalytic degradation of the organic dye Rhodamine B, exhibiting remarkable adsorption and degradation ability. Photophysical tests further elucidated the degradation mechanism and corroborated the photocatalytic application potential of these DA-POPs. This work brings a new synthetic strategy for the elaboration of POPs for reducing environmental pollution via photocatalytic waste degradation.

Strategic design of a rare trigonal symmetric luminescent covalent organic framework by linker modification

We designed a trigonal symmetric imine-linked covalent organic framework (COF), TFPC-DAB, with control over the angularity of the building units, where a bent C2-symmetric diamine, such as 1,3-diaminobenzene (1,3-DAB or DAB), with an exo-angle of 120° was used instead of those with an exo-angle of 180°, in combination with a C3-symmetric trialdehyde, such as tri(4-formylphenoxy)cyanurate (TFPC). Its synthesis was accomplished by reacting the building units in a mixture of mesitylene/dioxane/6 M acetic acid under solvothermal conditions. The phase purity, thermal stability, and porosity of TFPC-DAB were established by various analytical techniques. Utilizing the Density Functional Tight Binding (DFTB+) simulation and Pawley refinement, the best fit of the small angle x-ray pattern was found to have an AA stacking of TFPC-DAB in the trigonal space group P3 with low refinement parameters. Such smart materials are in huge demand to detect hazardous corrosive chemicals, such as HCl and NH3. The dual features of electron deficient π-acidic triazine moiety and heteroatoms (N/O) from TFPC and electron rich phenyl units from DAB embodied in the framework enhance its luminescent property and thereby make it suitable for solvent-based HCl and NH3 sensing. The detection limits for HCl and NH3 in methanol were found to be 14 and 82 ppb, respectively. The effect of solvent polarity on the sensing studies was observed with much lower detection limits in dioxane: 2.5 and 11 ppb for HCl and NH3, respectively. A detailed theoretical calculation using density functional theory and configurational bias Monte Carlo modules was conducted for understanding interactions between the COF and HCl or NH3 analytes.

Development of Porous Organic Polymers as Metal‐Free Photocatalysts for the Aromatization of N‐Heterocycles

AbstractPorous organic polymers (POPs), and especially covalent triazine frameworks (CTFs), are being developed as the next generation of metal‐free heterogeneous photocatalysts. However, many of the current synthetic routes to obtain these photoactive POPs require expensive monomers and rely on precious metal catalysts, thus hindering their widespread implementation. In this work, a range of POPs was synthesized from simple unfunctionalized aromatic building blocks, through Lewis acid‐catalyzed polymerization. The obtained materials were applied, for the first time, as heterogeneous photocatalysts for the aromatization of N‐heterocycles. With the use of the most active material, denoted as CTF‐Pyr, which consists of photoactive pyrene and triazine moieties, a wide range of pyridines, dihydroquinoline‐5‐ones, tetrahydroacridine‐1,8‐diones and pyrazoles were obtained in excellent yields (70–99 %). Moreover, these reactions were carried out under very mild conditions using air and at room temperature, highlighting the potential of these materials as catalysts for green transformations.

Surface‐enhanced Raman scattering of carbazole‐based covalent triazine framework

AbstractA kind of carbazole‐based covalent triazine framework (CTF‐Cz) has been synthesized from a carbazole derivative. The porous polymer can efficiently adsorb probe molecules due to the strong intermolecular interactions caused by the polar triazine moiety. CTF‐Cz directly serves as the surface‐enhanced Raman scattering substrate without any post proceeding techniques. The enhancement factor of CTF‐Cz is ~105 for detecting rhodamine 6G (R6G). The lowest unoccupied molecular orbital energy level of CTF‐Cz (−3.93 eV) is much lower than that of R6G, which is in favor of the charge transfer from R6G to CTF‐Cz for illumination under a 532 nm laser, which is proved by time resolved photoluminescence spectra. The efficient charge transfer induced by the strong intermolecular π–π interactions and large molecular‐orbital delocalization contribute to the enhanced Raman signals of R6G on CTF‐Cz.

Sequential activation strategy of triazinyl resorufin for high selectivity fluorescence GSH detection

The abnormally elevated expression level of glutathione (GSH) has been observed in various human cancer cells and tissue. Thus, effective methods for glutathione detection are of great importance in early diagnosis of cancer. However, many fluorescent probes for GSH detection suffer from the interference of the abundantly existent nucleophilic biomolecules in biological environment. In this work, we propose a sequential activation strategy to overcome this problem by designing and synthesizing a series of 1,3,5-triazinyl resorufin turn-on fluorescent probe (Probes 1–3). As two electrophilic sites are presented in probes, GSH sequentially reacts with the resorufin and the triazine moiety, resulting in significant fluorescence augmentation (up to 165.0-fold). Designed probes possess low limit of detection as low as 1.8 μM). Cellular fluorescent imaging has been successfully applied to selectively detect GSH in several living cells.

The Synergistic Effect of Triazine and Phosphaphenanthrene Units on the Physico-Chemical Behavior of Polyimides.

With the aim to develop polymers with appealing, multifunctional characteristics, a series of polyimides were designed by anchoring 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO) units on the main polymer chains containing 1,3,5-triazine and several flexible moieties, such as ether, hexafluoroisopropylidene, or isopropylidene. A detailed study was conducted to establish structure-property correlations, with a focus on the synergistic effectiveness of triazine and DOPO moieties on the overall features of polyimides. The results evidenced good solubility of the polymers in organic solvents, their amorphous nature with short-range regular-packed polymer chains, and high thermal stability with no glass transition temperature below 300 °C. Spectrophotometric measurements revealed the existence of a strong charge transfer complex in these polymers that led to a "black" appearance, which generated broad absorption bands spanning on the overall visible range. Nevertheless, these polymers displayed green light emission associated with 1,3,5-triazine emitter. The electrochemical characteristics of the polyimides in solid state demonstrated their strong n-type doping character induced by three different structural elements with electron-acceptance capability. The useful properties of these polyimides, including optical, thermal, electrochemical, aesthetics, and opaqueness, endow them with several possible applications in the microelectronic field, such as protecting layers for the inner circuits against UV light deterioration.

Highly efficient electrocatalytic CO2 reduction over pyrolysis–free conjugated metallophthalocyanine networks in full pH range

Herein, we report the first work on pyrolysis–free synthesis of robust conjugated metallophthalocyanine–based covalent triazine frameworks (MPc–CTF, M= Co, Ni) for pH-universal electrocatalytic CO2 reduction reaction (CO2RR). CoPc–CTF shows high CO Faradaic efficiency over 94%, and long-term stability over 10 h in full pH range, and industry level CO partial current densities of 378.8 mA cm−2, 165.9 mA cm−2, 172.5 mA cm−2 in alkaline, neutral and acidic electrolytes, respectively. Particularly, the CO2 utilization efficiency reaches 51.3% in acidic electrolytes. Moreover, operando characterizations and density functional theory calculations indicate the promoting effect of triazine moiety in CoPc–CTF to accelerate the formation of *COOH intermediates during CO2RR. This work provides an encouraging direction for designing robust conjugated network supported single site catalysts to access high product selectivity and high carbon utilization efficiency in electrocatalytic CO2 reduction reaction.

Peptide Stapling through Site-Directed Conjugation of Triazine Moieties to the Tyrosine Residues of a Peptide

Peptide stapling is a strategy for improving the biological properties of peptides. Herein, we report a novel method for stapling peptides that utilizes bifunctional triazine moieties for two-component conjugation to the phenolic hydroxyl groups of tyrosine, which enables efficient stapling of unprotected peptides. In addition, we applied this strategy to the RGD peptide that can target integrins and demonstrated that the stapled RGD peptide had significantly improved plasma stability and integrin-targeting ability.

Potent heteroaromatic hydrazone based 1,2,4-triazine motifs: synthesis, anti-oxidant activity, cholinesterase inhibition, quantum chemical and molecular docking studies

1,2,4-Triazine based hydrazone scaffolds possessing impressive biological activities are synthesized using heteroaromatic aldehydes. The target molecules were characterized by detailed spectroscopic techniques. Anti-oxidant capacities of target compounds were determined using DPPH free radical scavenging activity, ABTS method and superoxide anion scavenging assay by means of NBT. Compound 4a displayed potent anti-oxidant potential against ABTS having IC50 28.09 ± 0.15 µM comparative to the standard Trolox (26.01 ± 0.02 µM). Cholinesterase inhibitory potentials of the synthesized compounds were also evaluated, where compound 4b intensely inhibited against AChE and BChE in dose dependent method compared to standard drugs, allanzanthane and galantamine. The IC50 value of compound 4b for AChE was 15.24 ± 0.03 µM vs 10.13 ± 0.01 for allanzanthane and 13.01 ± 0.02 for galantamine, whereas, IC50 value of 4b for BChE was 17.01 ± 0.6 µM vs 22.00 ± 0.01 for allanzanthane and 26.02 ± 0.09 for galantamine. Density functional theory (DFT) simulations of synthesized compounds (4a-c) complement the experimental spectroscopic data (FTIR, 1H & 13C NMR & UV–Visible). The HOMO-LUMO energy gaps of 3.58 eV to 3.80 eV reflect the kinetic stability of the compounds (4a-c). Moreover, the MEP analysis confirmed the chemical reactivities of these compounds and more nucleophilic sites were identified at the heteroatoms of heterocyclic moiety and triazine moiety. In silico molecular docking study revealed that our active targeted compounds have minimum binding energy and good affinity toward the active pocket of target protein. These results showed that our synthesized compounds are excellent inhibitors of AChE & BChE enzymes, and therefore, can be subjected to further studies in order to accomplish potent drug responsible for the treatment of Alzheimer's disease.

Three-Component Donor-π-Acceptor Covalent-Organic Frameworks for Boosting Photocatalytic Hydrogen Evolution.

Two-dimensional covalent-organic frameworks (2D COFs) have recently emerged as great prospects for their applications as new photocatalytic platforms in solar-to-hydrogen conversion; nevertheless, their inefficient solar energy capture and fast charge recombination hinder the improvement of photocatalytic hydrogen production performance. Herein, two photoactive three-component donor-π-acceptor (TCDA) materials were constructed using a multicomponent synthesis strategy by introducing electron-deficient triazine and electron-rich benzotrithiophene moieties into frameworks through sp2 carbon and imine linkages, respectively. Compared with two-component COFs, the novel TCDA-COFs are more convenient in regulating the inherent photophysical properties, thereby realizing outstanding photocatalytic activity for hydrogen evolution from water. Remarkably, the first sp2 carbon-linked TCDA-COF displays an impressive hydrogen evolution rate of 70.8 ± 1.9 mmol g-1 h-1 with excellent reusability in the presence of 1 wt % Pt under visible-light illumination (420-780 nm). Utilizing the combination of diversified spectroscopy and theoretical prediction, we show that the full π-conjugated linkage not only effectively broadens the visible-light harvesting of COFs but also enhances charge transfer and separation efficiency.

D-π-A array structure of Bi4Ti3O12-triazine-aldehyde group benzene skeleton for enhanced photocatalytic uranium (VI) reduction

Photocatalytic reduction of UVI to UIV can help remove U from the environment and thus reduce the harmful impacts of radiation emitted by uranium isotopes. Herein, we first synthesized Bi4Ti3O12 (B1) particles, then B1 was crosslinked with 6-chloro-1,3,5-triazine-diamine (DCT) to afford B2. Finally, B3 was formed using B2 and 4-formylbenzaldehyde (BA-CHO) to investigate the utility of the D-π-A array structure for photocatalytic UVI removal from rare earth tailings wastewater. B1 lacked adsorption sites and displayed a wide band gap. The grafted triazine moiety in B2 introduced active sites and narrowed the band gap. Notably, B3, a Bi4Ti3O12 (donor)-triazine unit (π-electron bridge)-aldehyde benzene (acceptor) molecule, effectively formed the D-π-A array structure, which formed multiple polarization fields and further narrowed the band gap. Therefore, UVI was more likely to capture electrons at the adsorption site of B3 and be reduced to UIV due to energy level matching effects. UVI removal capacity of B3 under simulated sunlight was 684.9 mg g−1, 2.5 times greater than B1 and 1.8 times greater than B2. B3 was still active after multiple reaction cycles, and UVI removal from tailings wastewater reached 90.8%. Overall, B3 provides an alternative design scheme for enhancing photocatalytic performance.

Covalent Organic Frameworks Containing Dual O2 Reduction Centers for Overall Photosynthetic Hydrogen Peroxide Production.

Covalent organic frameworks (COFs) are highly desirable for achieving high-efficiency overall photosynthesis of hydrogen peroxide (H2 O2 ) via molecular design. However, precise construction of COFs toward overall photosynthetic H2 O2 remains a great challenge. Herein, we report the crystalline s-heptazine-based COFs (HEP-TAPT-COF and HEP-TAPB-COF) with separated redox centers for efficient H2 O2 production from O2 and pure water. The spatially and orderly separated active sites in HEP-COFs can efficiently promote charge separation and enhance photocatalytic H2 O2 production. Compared with HEP-TAPB-COF, HEP-TAPT-COF exhibits higher H2 O2 production efficiency for integrating dual O2 reduction active centers of s-heptazine and triazine moieties. Accordingly, HEP-TAPT-COF bearing dual O2 reduction centers exhibits a remarkable solar-to-chemical energy efficiency of 0.65 % with a high apparent quantum efficiency of 15.35 % at 420 nm, surpassing previously reported COF-based photocatalysts.