Photochemical transformations of 5-methyltetrazole. Matrix isolation FTIR and DFT studies

Pagacz-Kostrzewa, Magdalena; Krupa, Justyna; Wierzejewska, Maria

doi:10.1016/j.jphotochem.2013.12.011

Cited by 14 publications

(16 citation statements)

References 44 publications

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“…Maier and co-workers demonstrated that upon UV exposure, tetrazole derivatives release molecular nitrogen to form products such as nitrilimine, carbodiimide, and cyanamide . Further studies by Wierzejewska and Rayat indicated that for simple tetrazole derivatives like 5-methyltetrazole and 1-methyltetrazole, carbidiimides were the principal products, while nitrilimine and cyanamide sometimes appeared.…”

Section: Resultsmentioning

confidence: 99%

Direct Wavelength-Selective Optical and Electron-Beam Lithography of Functional Inorganic Nanomaterials

et al. 2019

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Direct optical lithography of functional inorganic nanomaterials (DOLFIN) is a photoresist-free method for high-resolution patterning of inorganic nanocrystals (NCs) that has been demonstrated using deep UV (DUV, 254 nm) photons. Here, we expand the versatility of DOLFIN by designing a series of photochemically active NC surface ligands for direct patterning using various photon energies including DUV, near-UV (i-line, 365 nm), blue (h-line, 405 nm), and visible (450 nm) light. We show that the exposure dose for DOLFIN can be ∼30 mJ/cm2, which is small compared to most commercial photopolymer resists. Patterned nanomaterials can serve as highly robust optical diffraction gratings. We also introduce a general approach for resist-free direct electron-beam lithography of functional inorganic nanomaterials (DELFIN) which enables all-inorganic NC patterns with feature size down to 30 nm, while preserving the optical and electronic properties of patterned NCs. The designed ligand chemistries and patterning techniques offer a versatile platform for nano- and micron-scale additive manufacturing, complementing the existing toolbox for device fabrication.

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Section: Resultsmentioning

confidence: 99%

Direct Wavelength-Selective Optical and Electron-Beam Lithography of Functional Inorganic Nanomaterials

et al. 2019

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“…[16][17][18][22][23][24][25][26][27][28] Substituents were found to have a significant effect on the structural characteristics of nitrile imines. [16][17][18][22][23][24][25][26][27][28] Substituents were found to have a significant effect on the structural characteristics of nitrile imines.…”

Section: Introductionmentioning

confidence: 99%

“…Several nitrile imines have been captured in low-temperature matrices and characterized spectroscopically. [16][17][18][22][23][24][25][26][27][28] Substituents were found to have a significant effect on the structural characteristics of nitrile imines. This is particularly noticeable by the CNN antisymmetric stretching IR absorption of the nitrile imine moiety appearing over a wide range of frequencies (2000-2250 cm -1 ).…”

Section: Introductionmentioning

confidence: 99%

The Quest for Carbenic Nitrile Imines: Experimental and Computational Characterization of C‐Amino Nitrile Imine

et al. 2015

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C‐Amino nitrile imine has been generated as primary photoproduct (λ = 220 nm) of 5‐amino‐2H‐tetrazole isolated in an argon matrix at 15 K. Subsequent photochemical experiments (λ = 330 nm) demonstrated that C‐amino nitrile imine isomerizes to the corresponding three‐membered‐ring 1H‐diazirine and decomposes to methylenimine. The experimentally observed νas(CNN) absorption at 1998 cm–1 and a carbenic resonance structure contribution of around 20 %, predicted by natural resonance theory calculations, demonstrate that the protoproduced C‐amino nitrile imine has significant carbenic character. These results pave the way to the discovery of carbenic nitrile imines.

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“…Although the photochemistry of tetrazole derivatives has been the subject of a number of studies, the photolysis of triazoles was rarely investigated until now. − In the unsubstituted triazole molecule, N 2 or HCN elimination is the main pathway of UV photolysis leading to formation of such products as hydrogen cyanide N -methylide, or cyanamide, carbodiimide, and nitrilimine …”

Section: Introductionmentioning

confidence: 99%

Phototransformations of 2-(1,2,4-Triazol-3-yl)benzoic Acid in Low Temperature Matrices

et al. 2019

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Phototransformations of 2-(1,2,4-triazol-3-yl)benzoic acid induced by tunable UV laser were studied in low temperature matrices by FTIR spectroscopy. Out of 36 possible isomers of this molecule the most stable one, comprising the intramolecular N−H•••O hydrogen bond, was detected experimentally in argon and xenon matrices after deposition. Upon irradiation with λ = 325 nm, two new conformers of the precursor were formed. The corresponding reverse photorotamerizations were also detected at 250 nm partly reproducing the initial molecules. In addition to the conformational changes, an interesting photoisomerization took place in the studied matrices leading to a proton transfer from N atom of the triazole ring to the carbonyl oxygen of the carboxylic group. As a result of this reaction, a new product with two OH groups was identified for the first time. The experimental studies were supported by DFT calculations in both ground and excited electronic states.

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Photochemical transformations of 5-methyltetrazole. Matrix isolation FTIR and DFT studies

Cited by 14 publications

References 44 publications

Direct Wavelength-Selective Optical and Electron-Beam Lithography of Functional Inorganic Nanomaterials

Direct Wavelength-Selective Optical and Electron-Beam Lithography of Functional Inorganic Nanomaterials

The Quest for Carbenic Nitrile Imines: Experimental and Computational Characterization of C‐Amino Nitrile Imine

Phototransformations of 2-(1,2,4-Triazol-3-yl)benzoic Acid in Low Temperature Matrices

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