Tri-s-triazine: synthesis, chemical behavior, and spectroscopic and theoretical probes of valence orbital structure

Shahbaz, M.; Urano, Shigeyuki; Lebreton, Pierre; Rossman, Mitchell A.; Hosmane, Ramachandra S.; Leonard, Nelson J.

doi:10.1021/ja00322a014

Cited by 86 publications

(69 citation statements)

References 3 publications

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“…[10] However, it was not proven until almost fifty years later when the crystal structure of molecular s-heptazine C 6 N 7 H 3 could be solved. [11] Due to the low solubility of sheptazines in common solvents, this building unit is considerably less frequently employed in chemical syntheses than s-triazine compounds. However, in the last two decades carbon nitride type compounds have attracted considerable interest as materials for numerous technical applications due to the high thermal and oxidation stability of this class of compounds as well as their semiconducting and catalytic properties.…”

Section: Introductionmentioning

confidence: 99%

Formation of a Hydrogen‐Bonded Heptazine Framework by Self‐Assembly of Melem into a Hexagonal Channel Structure

Makowski

Köstler

Schnick

2012

Chemistry A European J

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Self-assembly of melem C(6)N(7)(NH(2))(3) in hot aqueous solution leads to the formation of hydrogen-bonded, hexagonal rosettes of melem units surrounding infinite channels with a diameter of 8.9 Å. The channels are filled with strongly disordered water molecules, which are bound to the melem network through hydrogen bonds. Single-crystals of melem hydrate C(6)N(7)(NH(2))(3)⋅xH(2)O (x≈2.3) were obtained by hydrothermal treatment of melem at 200 °C and the crystal structure (R ̅3c, a=2879.0(4), c=664.01(13) pm, V=4766.4(13)×10(6) pm(3), Z=18) was elucidated by single-crystal X-ray diffraction. With respect to the structural similarity to the well-known adduct between melamine and cyanuric acid, the composition of the obtained product was further analyzed by solid-state NMR spectroscopy. Hydrolysis of melem to cyameluric acid during syntheses at elevated temperatures could thus be ruled out. DTA/TG studies revealed that, during heating of melem hydrate, water molecules can be removed from the channels of the structure to a large extent. The solvent-free framework is stable up to 430 °C without transforming into the denser structure of anhydrous melem. Dehydrated melem hydrate was further characterized by solid-state NMR spectroscopy, powder X-ray diffraction, and sorption measurements to investigate structural changes induced by the removal of water from the channels. During dehydration, the hexagonal, layered arrangement of melem units is maintained whereas the formation of additional hydrogen bonds between melem entities requires the stacking mode of hexagonal layers to be altered. It is assumed that layers are shifted perpendicular to the direction of the channels, thereby making them inaccessible for guest molecules.

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Section: Introductionmentioning

confidence: 99%

Formation of a Hydrogen‐Bonded Heptazine Framework by Self‐Assembly of Melem into a Hexagonal Channel Structure

Makowski

Köstler

Schnick

2012

Chemistry A European J

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“…The calculated energies for the addition of one equivalent of hydrogen suggest that 1,3,5-triazine has lower resonance energy than benzene, pyridine, pyrazine and pyrimidine, which have essentially the same resonance energy [426]. Photoelectron spectra of 1,3,5-triazines have been recorded [427] and the parent compound 3 shows five major bands [428].…”

Section: 41mentioning

confidence: 98%

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Oliva¹,

Laza²,

Ocáriz³

2011

Modern Heterocyclic Chemistry

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“…The protonation will make g-C 3 N 4 decompose to clusters or oligomers of condensed triazine rings. [20] As a result, parts of the clusters or oligomers with good water solubility will be removed by decomposition under hydrothermal conditions [21] to form the porous structure in g-C 3 N 4 . Moreover, it is noteworthy that the BP-CN obtained from the bulk and dense B-CN (Case I) can only …”

Section: Morphology Characteristicsmentioning

confidence: 99%

Template‐Free Synthesis of Three‐Dimensional Nanoporous Bulk Graphitic Carbon Nitride with Remarkably Enhanced Photocatalytic Activity and Good Separation Properties

et al. 2015

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A facile template-free method is presented for the fabrication of three-dimensional (3D) nanoporous bulk graphitic carbon nitride (g-C 3 N 4 ) with an interconnected framework. Various techniques, namely, X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, elemental analysis, specific surface area measurements (Brunauer-Emmett-Teller method), UV/Vis diffuse reflectance spectroscopy, timeresolved fluorescence decay spectroscopy, electron paramagnetic resonance spectroscopy, and photoelectrochemical measurements, were adopted to analyze the structures and physicochemical properties of the as-prpared samples. The results show that the nanoporous bulk g-C 3 N 4 with a particle size of ca. 20 μm exhibits a high specific surface area, which

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Tri-s-triazine: synthesis, chemical behavior, and spectroscopic and theoretical probes of valence orbital structure

Cited by 86 publications

References 3 publications

Formation of a Hydrogen‐Bonded Heptazine Framework by Self‐Assembly of Melem into a Hexagonal Channel Structure

Formation of a Hydrogen‐Bonded Heptazine Framework by Self‐Assembly of Melem into a Hexagonal Channel Structure

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Template‐Free Synthesis of Three‐Dimensional Nanoporous Bulk Graphitic Carbon Nitride with Remarkably Enhanced Photocatalytic Activity and Good Separation Properties

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