Azo dicarboxylates are not conjugated: X-ray crystal structure and theoretical calculations on di-t-butylazodicarboxylate

Goh, Mean See; Rintoul, Llew; Pfrunder, Michael C.; McMurtrie, John C.; Arnold, Dennis P.

doi:10.1016/j.molstruc.2015.06.027

Cited by 5 publications

(2 citation statements)

References 40 publications

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“…To gain insight into the electronic and structural properties of azodicarboxamide derivatives, we have performed quantum‐mechanical calculations on tetramethylazodicarboxamide. Detailed investigations of the conformational phase space in the electronic ground‐state reveals, in contrast to the parent compound 1,1′‐azobisformamide, a significantly nonplanar structure of the molecule (Figure a). The carbonyl groups are in this case rotated by about 75° with respect to the N=N bond (MP2/6‐31++G**) and point in opposite directions.…”

Section: Figurementioning

confidence: 99%

Photoinduced Pedalo‐Type Motion in an Azodicarboxamide‐Based Molecular Switch

et al. 2017

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Well‐defined structural changes of molecular units that can be triggered by light are crucial for the development of photoactive functional materials. Herein, we report on a novel switch that has azodicarboxamide as its photo‐triggerable element. Time‐resolved UV‐pump/IR probe spectroscopy in combination with quantum‐chemical calculations shows that the azodicarboxamide functionality, in contrast to other azo‐based chromophores, does not undergo trans–cis photoisomerization. Instead, a photoinduced pedalo‐type motion occurs, which because of its volume‐conserving properties enables the design of functional molecular systems with controllable motion in a confined space.

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Section: Figurementioning

confidence: 99%

Photoinduced Pedalo‐Type Motion in an Azodicarboxamide‐Based Molecular Switch

et al. 2017

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“…To gain insight into the electronic and structural properties of azodicarboxamide derivatives,w eh ave performed quantum-mechanical calculations on tetramethylazodicarboxamide.D etailed investigations of the conformational phase space in the electronic ground-state reveals,incontrast to the parent compound 1,1'-azobisformamide, [38,39] as ignificantly nonplanar structure of the molecule (Figure 2a). The carbonyl groups are in this case rotated by about 758 8 with respect to the N=Nb ond (MP2/6-31 ++G**) and point in opposite directions.F urther support for this conclusion is provided by our experimental UV/Vis and IR absorption spectra, which are in excellent agreement with the corresponding results obtained by density functional theory calculations (B3LYP/6-31G(d,p), see Figures S1 and S2 in the Supporting Information).…”

Section: Switchingbetweentwoormorestatesonthemolecularlevelmentioning

confidence: 99%

Photoinduced Pedalo‐Type Motion in an Azodicarboxamide‐Based Molecular Switch

et al. 2017

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Well-defined structural changes of molecular units that can be triggered by light are crucial for the development of photoactive functional materials.Herein, we report on anovel switch that has azodicarboxamide as its photo-triggerable element. Time-resolved UV-pump/IR probe spectroscopyi n combination with quantum-chemical calculations shows that the azodicarboxamide functionality,i nc ontrast to other azobased chromophores,does not undergo trans-cis photoisomerization. Instead, ap hotoinduced pedalo-type motion occurs, which because of its volume-conserving properties enables the design of functional molecular systems with controllable motion in aconfined space.

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Synthesis of Naphthalimide Azocarboxylates Showing Turn‐On Fluorescence by Substitution Reaction with Sulfinates**

Tanimoto,

Kyogaku,

Otsuki

et al. 2024

Chemistry An Asian Journal

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The synthesis and characterization of sulfinate addition‐responsive fluorescent molecules are described. We found that addition reaction of sulfinates to naphthalimide‐substituted azocarboxylates afforded the corresponding sulfonyl hydrazides with high fluorescence quantum yields (up to 0.91 in THF and 0.54 in methanol), which exhibited a large Stokes shift (105 nm) in protic methanol solvent, while the unsubstituted hydrazide and the sulfonyl‐position isomer showed no fluorescence in polar solvents.

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Azo dicarboxylates are not conjugated: X-ray crystal structure and theoretical calculations on di-t-butylazodicarboxylate

Cited by 5 publications

References 40 publications

Photoinduced Pedalo‐Type Motion in an Azodicarboxamide‐Based Molecular Switch

Photoinduced Pedalo‐Type Motion in an Azodicarboxamide‐Based Molecular Switch

Photoinduced Pedalo‐Type Motion in an Azodicarboxamide‐Based Molecular Switch

Synthesis of Naphthalimide Azocarboxylates Showing Turn‐On Fluorescence by Substitution Reaction with Sulfinates**

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