Crystal structure of 4-(prop-2-ynyloxy)-2,2,6,6-tetramethylpiperidin-1-oxyl

Goswami, Shailesh K.; Hanton, Lyall R.; McAdam, C. John; Moratti, Stephen C.

doi:10.1107/s1600536814017991

Cited by 4 publications

(5 citation statements)

References 27 publications

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“…Because also using 29 Si-NMR one cannot see any cleavage of the Si À Cb ond, one can assign the desired composition Si 2 O 3 C 6 H 3 N 3 to the obtained materials. Thec hemical shift of the 13 CNMR signals fits very well to those from the precursor.I nF T-IR one can clearly identify the characteristic vibrations for the azide group (n asym = 2100 cm À1 ; n sym = 1284 cm À1 ).…”

Section: Methodsmentioning

confidence: 99%

“…The success of our method can be monitored directly by imaging techniques, for instance electron paramagnetic spectroscopy (EPR) imaging 28. For this purpose 4‐ethynyloxy‐2,2,6,6‐tetramethylpiperidin‐1‐oxyl (see S‐7e), an alkyne, containing a persistent TEMPO nitroxide radical derivative, was synthesized and used for the click reaction 29. The EPR spectrum of the attached TEMPO derivative shown in S‐11 is characteristic for a probe with an anisotropic and reduced rotation caused by the successful attachment to the surface.…”

Section: Methodsmentioning

confidence: 99%

“…[28] Forthis purpose 4ethynyloxy-2,2,6,6-tetramethylpiperidin-1-oxyl (see S-7e), an alkyne,c ontaining ap ersistent TEMPO nitroxide radical derivative,was synthesized and used for the click reaction. [29] TheEPR spectrum of the attached TEMPO derivative shown in S-11 is characteristic for ap robe with an anisotropic and reduced rotation caused by the successful attachment to the surface.T he spectroscopic information was used for EPR imaging analysis for separation of the spatial information by…”

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confidence: 99%

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Directional Materials—Nanoporous Organosilica Monoliths with Multiple Gradients Prepared Using Click Chemistry

et al. 2015

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The existence of more than one functional entity is fundamental for materials, which are desired of fulfilling complementary or succeeding tasks. Whereas it is feasible to make materials with a homogeneous distribution of two different, functional groups, cases are extremely rare exhibiting a smooth transition from one property to the next along a defined distance. We present a new approach leading to high-surface area solids with functional gradients at the microstructural level. Periodically ordered mesoporous organosilicas (PMOs) and aerogel-like monolithic bodies with a maximum density of azide groups were prepared from a novel sol-gel precursor. The controlled and fast conversion of the azide into numerous functions by click chemistry is the prerequisite for the implementation of manifold gradient profiles. Herein we discuss materials with chemical, optical and structural gradients, which are interesting for all applications requiring directionality, for example, chromatography.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Directional Materials—Nanoporous Organosilica Monoliths with Multiple Gradients Prepared Using Click Chemistry

et al. 2015

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“…[29] TheEPR spectrum of the attached TEMPO derivative shown in S-11 is characteristic for ap robe with an anisotropic and reduced rotation caused by the successful attachment to the surface.T he spectroscopic information was used for EPR imaging analysis for separation of the spatial information by …”

Section: à2mentioning

confidence: 99%

“…Am ass loss step (Dm = À12 %) is observed at T = 188 8 8C, which can be assigned to the loss of one nitrogen molecule from the organosilica material. Because also using 29 Si-NMR one cannot see any cleavage of the Si À Cb ond, one can assign the desired composition Si 2 O 3 C 6 H 3 N 3 to the obtained materials.…”

Section: à2mentioning

confidence: 99%

Directional Materials—Nanoporous Organosilica Monoliths with Multiple Gradients Prepared Using Click Chemistry

et al. 2015

View full text Add to dashboard Cite

The existence of more than one functional entity is fundamental for materials,w hich are desired of fulfilling complementary or succeeding tasks.W hereas it is feasible to make materials with ah omogeneous distribution of two different, functional groups,cases are extremely rare exhibiting as mooth transition from one property to the next along adefined distance.Wepresent anew approach leading to highsurface area solids with functional gradients at the microstructural level. Periodically ordered mesoporous organosilicas (PMOs) and aerogel-like monolithic bodies with am aximum density of azide groups were prepared from anovel solgel precursor.T he controlled and fast conversion of the azide into numerous functions by clickc hemistry is the prerequisite for the implementation of manifold gradient profiles.H erein we discuss materials with chemical, optical and structural gradients,w hicha re interesting for all applications requiring directionality,for example,chromatography.

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Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

et al. 2019

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The 2-(prop-2-yn-1-yloxy)naphthalene (compound I) and 1nitro-2-(prop-2-yn-1-yloxy)benzene (compound II) were prepared in excellent yields by the reaction of propargyl bromide with 2-naphthol and 2-nitrophenol, respectively. Structural and conformational properties of both compounds have been analyzed using a combined approach including single-crystal X-ray diffraction and quantum chemical calculations. Two forms are found to be stable and nearly isoenergetic conformers, depending on the mutual orientation of the C � C triple bond and the O-C single bond of the prop-2-yn-1-yloxy group. The gauche conformation is the most stable form for the vacuum isolated species, with the anti conformation higher in energy by 1.00 and 1.89 kcal/mol computed at the M06-2X/6-311 + + G(d,p) level of approximation, for I and II, respectively. The gauche form is observed in the crystal of I but the nearly planar anti conformation is adopted in the crystalline phase of compound II. The occurrence of C-H⋅⋅⋅π and C-H⋅⋅⋅O intermolecular interactions involving the acidic -C � C-H hydrogen donor and -C � C-and -OCH 2 -acceptors is discussed. Furthermore, vibrational features of the prop-2-yn-1-yloxy moiety are analyzed by infrared and Raman spectroscopy. The UV-Vis spectrum shows the presence of well-defined absorption at ca. 280 and 320 nm assigned to the π!π* transitions in the naphtyl/benzyl and prop-2-yn-1-yloxy groups, respectively.

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Crystal structure of 4-(prop-2-ynyloxy)-2,2,6,6-tetramethylpiperidin-1-oxyl

Cited by 4 publications

References 27 publications

Directional Materials—Nanoporous Organosilica Monoliths with Multiple Gradients Prepared Using Click Chemistry

Directional Materials—Nanoporous Organosilica Monoliths with Multiple Gradients Prepared Using Click Chemistry

Directional Materials—Nanoporous Organosilica Monoliths with Multiple Gradients Prepared Using Click Chemistry

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

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