The infrared spectra of the aryl boronate esters derived from catechol and 2 : 3 dihydroxynaphthalene

Butcher, F.K.; Gerrard, W.; Howarth, Mark; Mooney, E.F.; Willis, H.A.

doi:10.1016/0371-1951(64)80203-4

Cited by 9 publications

(5 citation statements)

References 9 publications

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“…, any O − H stretching mode around 3300 cm ‐1 , which appears for pure arylboronic acids did not appear in the IR spectra of pure solid arylboronic acid catechol cyclic esters studied in this work. Most vibration modes are observed as in the literature, that is, C − O stretching modes were observed around 1237 and 1030 cm ‐1 , whereas B − O stretching modes were observed around 1329 and 1070 cm ‐1 . As in the case of the arylboronic acids, the C − C stretching mode was observed around 1600 cm ‐1 for arylboronic acid catechol cyclic esters.…”

Section: Resultssupporting

confidence: 56%

Solid‐state ¹¹B and ¹³C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Weiss

Kerneghan

et al. 2012

Magnetic Reson in Chemistry

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Nine arylboronic acids, seven arylboronic catechol cyclic esters, and two trimeric arylboronic anhydrides (boroxines) are investigated using (11)B solid-state NMR spectroscopy at three different magnetic field strengths (9.4, 11.7, and 21.1 T). Through the analysis of spectra of static and magic-angle spinning samples, the (11)B electric field gradient and chemical shift tensors are determined. The effects of relaxation anisotropy and nutation field strength on the (11)B NMR line shapes are investigated. Infrared spectroscopy was also used to help identify peaks in the NMR spectra as being due to the anhydride form in some of the arylboronic acid samples. Seven new X-ray crystallographic structures are reported. Calculations of the (11)B NMR parameters are performed using cluster model and periodic gauge-including projector-augmented wave (GIPAW) density functional theory (DFT) approaches, and the results are compared with the experimental values. Carbon-13 solid-state NMR experiments and spectral simulations are applied to determine the chemical shifts of the ipso carbons of the samples. One bond indirect (13)C-(11)B spin-spin (J) coupling constants are also measured experimentally and compared with calculated values. The (11)B/(10)B isotope effect on the (13)C chemical shift of the ipso carbons of arylboronic acids and their catechol esters, as well as residual dipolar coupling, is discussed. Overall, this combined X-ray, NMR, IR, and computational study provides valuable new insights into the relationship between NMR parameters and the structure of boronic acids and esters.

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Section: Resultssupporting

confidence: 56%

Solid‐state ¹¹B and ¹³C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Weiss

Kerneghan

et al. 2012

Magnetic Reson in Chemistry

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“…The comparison between the spectra indicates that the structural modification herein introduced by expanding the ligand from one to two condensed aromatic rings has important implications on the overall molecular rigidity. Indeed, in the middle-infrared region, most of the absorption peaks related to the aromatic skeleton vibrations of H 2 naph-cat are shifted toward higher energies, when compared to H 2 cat (Figure S16 in the Supporting Information) . The low-energy vibrations are also affected by the skeleton rigidity.…”

Section: Resultsmentioning

confidence: 98%

“…Indeed, in the middle-infrared region, most of the absorption peaks related to the aromatic skeleton vibrations of H 2 naph-cat are shifted toward higher energies, when compared to H 2 cat (Figure S16 in the Supporting Information). 33 The low-energy vibrations are also affected by the skeleton rigidity. Indeed, the predominant lowest energy absorption occurs at a frequency ca.…”

Section: Inorganic Chemistrymentioning

confidence: 99%

Structural Effects on the Spin Dynamics of Potential Molecular Qubits

et al. 2017

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Control of spin-lattice magnetic relaxation is crucial to observe long quantum coherence in spin systems at reasonable temperatures. Such a control is most often extremely difficult to achieve, because of the coexistence of several relaxation mechanisms, that is direct, Raman, and Orbach. These are not always easy to relate to the energy states of the investigated system, because of the contribution to the relaxation of additional spin-phonon coupling phenomena mediated by intramolecular vibrations. In this work, we have investigated the effect of slight changes on the molecular structure of four vanadium(IV)-based potential spin qubits on their spin dynamics, studied by alternate current (AC) susceptometry. The analysis of the magnetic field dependence of the relaxation time correlates well with the low-energy vibrational modes experimentally detected by time-domain THz spectroscopy. This confirms and extends our preliminary observations on the role played by spin-vibration coupling in determining the fine structure of the spin-lattice relaxation time as a function of the magnetic field, for S = / potential spin qubits. This study represents a step forward in the use of low-energy vibrational spectroscopy as a prediction tool for the design of molecular spin qubits with long-lived quantum coherence. Indeed, quantum coherence times of ca. 4.0-6.0 μs in the 4-100 K range are observed for the best performing vanadyl derivatives identified through this multitechnique approach.

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“…The characteristic C-H signals from the butane linker were retained in the FTIR spectrum of PNS, along with an additional stretch at 807 cm −1 . The additional stretch indicates the presence of a boronate ester 23 , as expected due to the two boronate esters in carboxy-PF1 prior to reaction with H 2 O 2 (see Fig. 1a for carboxy-PF1 structure and see Supplementary Fig.…”

Section: Methodsmentioning

confidence: 73%

An organic fluorophore-nanodiamond hybrid sensor for photostable imaging and orthogonal, on-demand biosensing

Purdey

Capon

Pullen

et al. 2017

Sci Rep

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Organic fluorescent probes are widely used to detect key biomolecules; however, they often lack the photostability required for extended intracellular imaging. Here we report a new hybrid nanomaterial (peroxynanosensor, PNS), consisting of an organic fluorescent probe bound to a nanodiamond, that overcomes this limitation to allow concurrent and extended cell-based imaging of the nanodiamond and ratiometric detection of hydrogen peroxide. Far-red fluorescence of the nanodiamond offers continuous monitoring without photobleaching, while the green fluorescence of the organic fluorescent probe attached to the nanodiamond surface detects hydrogen peroxide on demand. PNS detects basal production of hydrogen peroxide within M1 polarised macrophages and does not affect macrophage growth during prolonged co-incubation. This nanosensor can be used for extended bio-imaging not previously possible with an organic fluorescent probe, and is spectrally compatible with both Hoechst 33342 and MitoTracker Orange stains for hyperspectral imaging.

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The infrared spectra of the aryl boronate esters derived from catechol and 2 : 3 dihydroxynaphthalene

Cited by 9 publications

References 9 publications

Solid‐state ¹¹B and ¹³C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Solid‐state ¹¹B and ¹³C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Structural Effects on the Spin Dynamics of Potential Molecular Qubits

An organic fluorophore-nanodiamond hybrid sensor for photostable imaging and orthogonal, on-demand biosensing

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The infrared spectra of the aryl boronate esters derived from catechol and 2 : 3 dihydroxynaphthalene

Cited by 9 publications

References 9 publications

Solid‐state 11B and 13C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Solid‐state 11B and 13C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Structural Effects on the Spin Dynamics of Potential Molecular Qubits

An organic fluorophore-nanodiamond hybrid sensor for photostable imaging and orthogonal, on-demand biosensing

Contact Info

Product

Resources

About

Solid‐state ¹¹B and ¹³C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters

Solid‐state ¹¹B and ¹³C NMR, IR, and X‐ray crystallographic characterization of selected arylboronic acids and their catechol cyclic esters