A new electron rich network polymer: poly(1,3,5-triaminobenzene)

Johannsen, I.; Torrance, J. B.; Nazzal, A. I.

doi:10.1021/ma00192a010

Cited by 14 publications

(25 citation statements)

References 4 publications

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“…In addition to the pH‐dependent characteristic UV/Vis spectra, the formation of polyTAB nanosheets in the pH≈5.5 solution is another evidence for the presence of triaminobenzenium cations. We observed formation of polyTAB nanosheets (Figure 1, SI), known to occur upon polymerization of triaminobenzenium cations, thus confirming the presence of triaminobenzenium cations in the solution with pH≈5.5 …”

Section: Methodssupporting

confidence: 70%

“…The structure and position of the peaks in the two spectra are different due to different protonation patterns of TAB in the two solutions. In concentrated acid solution, the peak at 272 nm (Figure ) is evidence that protons attach to amine groups so that TAB is fully protonated . In neutral/moderately acidic solution the peak at 263 nm with a shoulder toward higher wavelengths (Figure ) is evidence of the presence of a triaminobenzenium ion, where protonation occurs not on the amino groups but on the ring carbon atom .…”

Section: Methodsmentioning

confidence: 99%

“…Protonation of TAB in acidic and near‐neutral solutions generates different species (Scheme ). The triaminobenzenium cation (Scheme , structure III) is the main product of protonation at room temperature at pH≈5.5, though a small amount of the amino‐protonated species (Scheme , structure IV) coexists with carbon ring protonated species (structure III) . By decreasing the pH, the three amine groups will eventually all be protonated (Scheme , structure II).…”

Section: Methodsmentioning

confidence: 99%

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Amine‐Directed Hydrogen‐Bonded Two‐Dimensional Supramolecular Structures

Afsari

Borguet

2016

ChemPhysChem

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Utilizing pure amine hydrogen bonding is a novel approach for constructing two-dimensional (2D) networks. Further, such systems are capable of undergoing structural modifications due to changes in pH. In this study, we designed a 2D network of triaminobenzene (TAB) molecules that by varying the pH from neutral to acidic, form either ordered or disordered structures on Au(111) surface as revealed in scanning tunneling microscopy images. In near-neutral solution (pH ≈5.5), protonation of TAB generates charged species capable of forming H-bonds between amine groups of neighboring molecules resulting in the formation of a 2D supramolecular structure on the electrified surface. At lower pH, due to the protonation of the amine groups, intermolecular hydrogen bonding is no longer possible and no ordered structure is observed on the surface. This opens the possibility to employ pH as a chemical trigger to induce a phase transition in the 2D molecular network of triaminobenzene molecules.

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Section: Methodssupporting

confidence: 70%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Amine‐Directed Hydrogen‐Bonded Two‐Dimensional Supramolecular Structures

Afsari

Borguet

2016

ChemPhysChem

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“…In organic solvent medium, first radical was formed in both the ―NH 2 groups because of addition of APS as an oxidative radical initiator. Then, it was oxidized to cyclohexa‐3, 5‐diene‐1, 2‐diylidenediamine just like oxidation of p‐phenylenediamine to diamine especially in non‐aqueous medium, and the polymerization was occurred through this derivative of o‐phenylenediamine. Both the NH groups of cyclohexa‐3, 5‐diene‐1, 2‐diylidenediamine were protonated by only one molecule of sulfuric acid formed by reduction of APS, just like oPD polymerization in sulfuric acid medium .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of poly(o -phenylenediamine) nanofiber with novel structure and properties

Samanta

Roy

Kar

2016

Polym. Adv. Technol.

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The poly(o‐phenylenediamine) (PoPD) was synthesized from the monomer o‐phenylenediamine in various organic solvent medium viz. dimethyl sulfoxide (DMSO), N,N‐dimethyl formamide (DMF) and methanol using ammonium per sulfate as a radical initiator. The structure just like polyaniline derivative with free NH functional groups of the synthesized polymers confirmed by various standard characterizations was explained from the proposed polymerization mechanism. All the synthesized polymers were completely soluble in common organic solvent like DMSO and DMF because of the presence of polar free NH functional groups in its structure. The formation of polymer nanofiber by reverse salting‐out process was confirmed, and the synthesized polymer in DMSO medium was the best polymer in terms of nano‐morphology as well as conducting properties. Interestingly, the average DC conductivity of undoped polymer film was recorded as 2.21 × 10−6 Scm−1 because of induced doping through self charge separation. Moreover, the conductivity of the polymer film was further increased to 1.16 × 10−3 Scm−1 after doping by sulfuric acid. Copyright © 2016 John Wiley & Sons, Ltd.

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“…, curves (a), (b) and (c) respectively. The peaks centered at 116−129 ppm are assigned to the hydrogen‐bonded carbon (C−H) in the benzenoid unit and the peaks at 138−142 ppm are attributed to the nitrogen‐bonded carbon (C−NH) in the benzenoid unit …”

Section: Resultsmentioning

confidence: 99%

Using aluminium triflate as a co‐catalyst for the polymerization of o‐phenylenediamine and its derivatives

Amer

Young

Vosloo

2013

Polymer International

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Aromatic diamine monomers, including o‐phenylenediamine (oPD), 4‐methyl‐o‐phenylenediamine (4Me‐oPD), 4,5‐dimethyl‐o‐phenylenediamine (dMe‐oPD) and 4‐(tert‐butyl)‐o‐phenylenediamine (tBu‐oPD), were polymerized by chemical oxidation using ammonium persulfate as an oxidant. Aluminium triflate (Al(OTf)3) was also used for the first time as a co‐catalyst under various reaction conditions for the polymerization of oPD derivatives. The polymerization yield was improved when Al(OTf)3 was introduced to the polymerization reaction for most polymers. The solubility of poly(4‐methyl‐o‐phenylenediamine) (P(4Me‐oPD)), poly(4,5‐dimethyl‐o‐phenylenediamine) (P(dMe‐oPD)) and poly(4‐(tert‐butyl)‐o‐phenylenediamine) (P(tBu‐oPD)) polymers was improved compared with the poly(o‐phenylenediamine) (P(oPD)) polymers in most common solvents. The homopolymers obtained were characterized by Fourier transform IR spectroscopy, UV−visible spectroscopy, 1H and 13C NMR, wide‐angle X‐ray diffraction, DSC and TGA. The results showed that the yield, solubility and structure of the polymers are significantly dependent on the polymerization conditions. DSC measurements indicated that the polymers exhibited melting and crystallization transitions. The polymers also showed good thermal stability and decompose above 400 °C in nitrogen. © 2013 Society of Chemical Industry

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A new electron rich network polymer: poly(1,3,5-triaminobenzene)

Cited by 14 publications

References 4 publications

Amine‐Directed Hydrogen‐Bonded Two‐Dimensional Supramolecular Structures

Amine‐Directed Hydrogen‐Bonded Two‐Dimensional Supramolecular Structures

Synthesis of poly(o -phenylenediamine) nanofiber with novel structure and properties

Using aluminium triflate as a co‐catalyst for the polymerization of o‐phenylenediamine and its derivatives

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