Triazine-based conjugated microporous polymers with N,N,N′,N′-tetraphenyl-1,4-phenylenediamine, 1,3,5-tris(diphenylamino)benzene and 1,3,5-tris[(3-methylphenyl)-phenylamino]benzene as the core for high iodine capture and fluorescence sensing of o-nitrophenol

Tong-mou, Geng; Ye, Sai-Nan; Zhu, Zongming; Zhang, Weiyong

doi:10.1039/c7ta08251g

Cited by 168 publications

(102 citation statements)

References 70 publications

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“…reported synthesis of CMPNs via olefin metathesis reaction using trifunctional styrene derivatives and studied its fluorescence quenching behavior for the detection of RDX at the picogram (pg) level . Few other CMPNs were reported for fluorescence‐based sensing of Hg(I), o ‐nitrophenol, nitroanilines, etc . In all the previous examples, the CMPNs were insoluble powders and often used as dispersion in solution or solid state for sensing applications.…”

Section: Cmpn Thin Films For Optical Sensingmentioning

confidence: 99%

Electrochemically Generated Conjugated Microporous Polymer Network Thin Films for Chemical Sensor Applications

Suresh

Scherf

2018

Macro Chemistry & Physics

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various chemicals with high sensitivity and shorter response times if compared to small molecules, linear polymer analogues, and other porous materials. [14] In most cases, CMPNs synthesized chemically via metal catalyzed C-C coupling reaction are insoluble, unprocessable powder solids, and pose difficulties to fabricate portable sensor devices. [1] In this regard, CMPN materials in the form of thin films are appropriate for the construction of portable detection devices and they also find applications in organic electronics and photovoltaics.Electrochemical oxidative polymerization technique is a promising approach to grow high-quality CMPN thin films with controlled thickness and surface roughness suitable for device fabrication. [15] It requires shorter times, easy purification process as it does not involve any metalcatalyst; hence the films are of high chemical purity and the films can be coated on various substrates including flexible electrodes. Electropolymerization is carried out in a cell connected to potentiostat and containing monomer solution with a supporting electrolyte, three electrodes viz. working electrode (WE) where the polymerization occurs, counter electrode (CE), and a reference electrode (RE). Electrochemical process of CMPN thin film preparation is understood in a similar way as electrochemical synthesis of linear conducting polymers described by Nelson, Lapkowski, and Ludwigs. [16] During the last few decades, studies on conducting polymers provided detailed understanding of polymerization process and effect of essential parameters such as applied potential, overoxidation, supporting electrolyte, temperature, and solvents on polymer growth and its properties. [16] All these studies were concentrated on electrochemical oxidation of bisubstituted monomers having carbazole, thiophene, or pyrrole functional groups to corresponding linear polymers for electrochromic devices, optoelectronics, and sensors applications. [17] Similar electrochemical principles were adopted for the fabrication of CMPN thin films using various multicarbazolyl or thienyl monomers having different aromatic cores for applications like organic solar cells, organic light emitting diodes, supercapacitors, and chemical sensors. [15] The scope of this short trend article is limited to CMPN films generated from carbazolyl-or thienyl-based monomers by electrochemical oxidative polymerization for electrochemical or optical-sensing applications. In the first part, preparation of CMPNs via electrochemical approach from multicarbazolyl-/ thienyl monomers containing different aromatic cores, their CMP Thin Film SensorsElectrogenerated π-conjugated microporous polymer network (CMPN) thin films are potential materials for highly sensitive detection of harmful chemical species as they show fast response, high signal amplification, and easy fabrication of devices. In the last few years, several CMPN thin films from carbazolyl and thienyl monomer building blocks having a variety of aromatic cores have been reported for different...

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Section: Cmpn Thin Films For Optical Sensingmentioning

confidence: 99%

Electrochemically Generated Conjugated Microporous Polymer Network Thin Films for Chemical Sensor Applications

Suresh

Scherf

2018

Macro Chemistry & Physics

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“…The moderate capacity originated from the low surface area. It was found that nitrogen-rich polymer favored the sorption toward iodine owing to the stronger interaction between nitrogen atom and electron-deficient I2 [4,[32][33]. The inserted images in Figure 4 showed the color change of I2-cyclohexane (1 mg ml -1 ) solution after adding 25 mg of CMOP-1 and CMOP-2.…”

Section: Gas Sorption Capacitymentioning

confidence: 99%

“…NAPOP-1 and NAPOP-3 exhibit high adsorption toward iodine (>240 wt%) and moderate CO2 adsorption [32]. Geng et al constructed novel triazine-based TCMPs by Friedel-Crafts polymerization reaction [33]. Among them, TTPPA displays excellent reversible iodine vapor uptake of 4.90 g g -1 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of nitrogen-rich polymers by click polymerization reaction and gas sorption property

Song

Duan

2018

Preprint

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Microporous organic polymers (MOPs) are promising materials for gas sorption because of the intrinsic and permanent porosity, designable framework and low density. The introduction of nitrogen-rich building block in MOPs will greatly enhance the gas sorption capacity. Here, we report the synthesis of MOPs from the 2,4,6-tris(4-ethynylphenyl)-1,3,5-triazine unit and aromatic azides linkers via click polymerization reaction. FTIR and solid state 13 C CP-MAS NMR confirm the formation of the polymers. CMOP-1 and CMOP-2 exhibit microporous networks with BET surface area of 431 and 406 m 2 g -1 and narrow pore size distribution under 1.2 nm. Gas sorption isotherms including CO2 and H2 were measured. CMOP-1 stores superior CO2 level of 8.2 wt% (1.88 mmol g -1 ) at 273 K/1.0 bar and H2 uptake up to 0.6 wt% at 77 K/1.0 bar, while CMOP-2 with smaller surface area shows lower CO2 adsorption capacity of 7.3 wt% (1.66 mmol˙g -1 ) and H2 uptake (0.5 wt%). In addition, I2 vapor adsorption was tested at 353 K. CMOP-1 shows higher gravimetric load of 160 wt%. Despite of the moderate surface area, the CMOPs display excellent sorption ability for CO2 and I2 due to the nitrogen-rich content in the polymers.

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“…In recent years, there was attracted considerable attention in the research of novel porous organic polymers (POPs) that have demonstrated great application prospect in iodine capture and fluorescence sensing to iodine and nitroaromatic compounds (NACs) . POPs have developed into a variety of types, including covalent organic frameworks (COFs), polymers of intrinsic microporosity (PIMs), hyper‐cross‐linked polymers (HCPs), covalent triazine‐based frameworks (CTFs), and conjugated microporous polymers (CMPs) …”

Section: Introductionmentioning

confidence: 99%

“…Friedel‐Crafts process catalysis has advantages of high cost‐effectiveness, mild synthetic conditions, good reproducibility, easy treatment, high yield, and high specific surface area . Methanesulfonic acid (CH 3 SO 3 H) and anhydrous aluminum chloride (AlCl 3 ) are commonly used catalysts in Friedel‐Crafts reaction. However, their catalytic effects are affected by the building block structure.…”

Section: Introductionmentioning

confidence: 99%

The preparation of covalent triazine‐based framework via Friedel‐Crafts reaction of 2,4,6‐trichloro‐1,3,5‐triazine with N,N′‐diphenyl‐N,N′‐di(m‐tolyl)benzidine for capturing and sensing to iodine

Tong-mou

Liu

Zhang

et al. 2020

Polymers for Advanced Techs

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The covalent triazine-based framework (TDPDB) has been prepared by Friedel-Crafts polymerization reaction of N,N 0 -diphenyl-N,N 0 -di(m-tolyl)benzidine (DPDB) with 2,4,6-trichloro-1,3,5-triazine (TCT) catalyzed by methanesulfonic acid. The yield of the reaction (94.85%) is very high. TDPDB was provided with Brunauer-Emmett-Teller specific surface area of 592.18 m 2 g −1 and pore volume of 0.5241 cm 3 g −1 .TDPDB demonstrated an excellent capacity for capturing iodine (3.93 g g −1 ) and an outstanding ability to fluorescent sensing to iodine with Ksv of 5.83 × 10 4 L mol −1 . It also showed high fluorescent sensing sensitivity to picric acid. K E Y W O R D S covalent triazine-based frameworks, fluorescent sensing, Friedel-Crafts reaction, iodine uptake, methanesulfonic acid

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Triazine-based conjugated microporous polymers with N,N,N′,N′-tetraphenyl-1,4-phenylenediamine, 1,3,5-tris(diphenylamino)benzene and 1,3,5-tris[(3-methylphenyl)-phenylamino]benzene as the core for high iodine capture and fluorescence sensing of o-nitrophenol

Abstract: A series of novel triazine-based conjugated microporous polymers were constructed via Friedel–Crafts polymerization.

Cited by 168 publications

References 70 publications

Electrochemically Generated Conjugated Microporous Polymer Network Thin Films for Chemical Sensor Applications

Electrochemically Generated Conjugated Microporous Polymer Network Thin Films for Chemical Sensor Applications

Synthesis of nitrogen-rich polymers by click polymerization reaction and gas sorption property

The preparation of covalent triazine‐based framework via Friedel‐Crafts reaction of 2,4,6‐trichloro‐1,3,5‐triazine with N,N′‐diphenyl‐N,N′‐di(m‐tolyl)benzidine for capturing and sensing to iodine

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