Supramolecular association of 1,2,5-chalcogenadiazoles: an unexpected self-assembled dissymetric [Se⋯N]2 four-membered ring

Berionni, Guillaume; Pégot, Bruce; Marrot, Jérôme; Goumont, Régis

doi:10.1039/b820258c

Cited by 36 publications

(41 citation statements)

References 14 publications

(19 reference statements)

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“…A few pertinent data referring to the N-alkylation reactions are collected in Table 2 for structural discussion. The NMR spectroscopic data collected for 7f,Me are in full agreement with those reported in the literature by Messmer et al [17] [22] [c] This work.…”

Section: Reactions Of Compounds 7a-f With Oxonium Saltssupporting

confidence: 82%

“…Experimental 1 H, 13 C, and 15 N NMR spectroscopic data have been already published and discussed in terms of correlation with theoretical data. [22] Good agreements between theoretical and experimental 1 H, 13 C, and 15 N NMR data were found, and calculations thus appeared to be a powerful tool for the structural elucidation of both neutral and cationic structures. A few pertinent data referring to the N-alkylation reactions are collected in Table 2 for structural discussion.…”

Section: Reactions Of Compounds 7a-f With Oxonium Saltsmentioning

confidence: 79%

“…In this particular case, the salt 7c,Me is obtained as the methyl www.eurjoc.orgester when the reaction is carried out with trimethyloxonium tetrafluoroborate salts (Scheme 2). [22] Scheme 3. Methylation of 7c.…”

Section: Reactions Of Compounds 7a-f With Oxonium Saltsmentioning

confidence: 99%

“…[18,22] This compound has been formulated on the basis of the X-ray structure given in Figure 1, which shows that addition of the methyl group takes place preferentially at N-3 rather than at N-2. [18] Figure 1.…”

Section: Reactions Of Compounds 7a-f With Oxonium Saltsmentioning

confidence: 99%

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The N‐Alkylation of Substituted 4‐Tetrazolo[1,5‐a]pyridines: Easy Access to a New Series of Electrophiles

et al. 2011

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A new series of homoleptic alkynyl complexes, [{Au2Cu2(C2R)4}n] (R=C3H7O (1), C6H11O (2), C9H19O (3), C13H11O (4)), were obtained from Au(SC4H8)Cl, Cu(NCMe)4PF6, and the corresponding alkyne in the presence of a base (NEt3). Complexes 1–4 aggregate upon crystallization into polymeric chains through extensive metallophilic interactions. The cluster that contains fluorenolyl functionalities, C13H9O (5), crystallizes in its molecular form as a disolvate, [Au2Cu2(C2C13H9O)4]⋅2 THF. The substitution of weakly bound THF molecules with pyridine molecules leads to the complex [Au2Cu2(C2C13H9O)4]⋅2 py (6), thus giving two polymorphs in the solid state. Such structural diversity is established through metal‐chain and hydrogen‐bond formation, which depends on the stereochemical characteristics of the organic ligands. More interestingly, this solid‐state structural arrangement affords good emission properties, such as intensity and spectroscopic profile, which are otherwise very weakly emissive in solution. Metallophilic aggregation of the {Au2Cu2} cluster units, as observed in the crystals, results in dramatic enhancement of the room‐temperature phosphorescence, thereby reaching a maximum quantum efficiency of 95 % (4). A theoretical approach further indicates a synergistic effect of the array of the metal chain upon aggregation, which greatly enhances the spin‐orbit coupling and, hence, the phosphorescence, thereby opening up a new direction in the field of aggregate‐enhanced emission.

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Section: Reactions Of Compounds 7a-f With Oxonium Saltssupporting

confidence: 82%

Section: Reactions Of Compounds 7a-f With Oxonium Saltsmentioning

confidence: 79%

Section: Reactions Of Compounds 7a-f With Oxonium Saltsmentioning

confidence: 99%

Section: Reactions Of Compounds 7a-f With Oxonium Saltsmentioning

confidence: 99%

See 2 more Smart Citations

The N‐Alkylation of Substituted 4‐Tetrazolo[1,5‐a]pyridines: Easy Access to a New Series of Electrophiles

et al. 2011

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“…The architectures are of current interest for supramolecular chemistry and crystal engineering. [26,27] In 6, the presence of two NH2 groups results in an extensive H-bonded network in the crystals. The strongest N-H…N bond (N…N 3.035 Å, NHN 171°) assembles the molecules into Se NMR spectra of 5f (above) and 5e (below) with isotropic resonances indicated by asterisks.…”

Section: Structure Elucidation By Xrd and 77 Se Nmrmentioning

confidence: 99%

[1,2,5]Selenadiazolo[3,4‐b]pyrazines: Synthesis from 3,4‐Diamino‐1,2,5‐selenadiazole and Generation of Persistent Radical Anions

et al. 2015

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Synthesis and Applications of 5‐Membered Chalcogen‐Nitrogen π‐Heterocycles with Three Heteroatoms

Ракитин

Zibarev

2018

Asian J Org Chem

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The recent progress in the synthesis of the title heterocycles exemplified by closed-and open-shell 1,2,5chalcogenadiazoles, 1,2,3-dichalcogenazoles and their hybrids (chalcogens: S, Se, and Te), and in actual or potential applications of these compounds in materials science and biomedicine, is discussed. The synthetic importance of the chalcogen exchange, both direct and indirect, is emphasized, as well as the significance of the heavier chalcogen derivatives in the design and synthesis of smart molecular materials.[a] Prof. Scheme 1.Representative examples of 1,2,5-chalcogenadiazoles and 1,2,3dichalcogenazoles including Appel and Herz cations and Herz radicals.

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Supramolecular association of 1,2,5-chalcogenadiazoles: an unexpected self-assembled dissymetric [Se⋯N]2 four-membered ring

Cited by 36 publications

References 14 publications

The N‐Alkylation of Substituted 4‐Tetrazolo[1,5‐a]pyridines: Easy Access to a New Series of Electrophiles

The N‐Alkylation of Substituted 4‐Tetrazolo[1,5‐a]pyridines: Easy Access to a New Series of Electrophiles

[1,2,5]Selenadiazolo[3,4‐b]pyrazines: Synthesis from 3,4‐Diamino‐1,2,5‐selenadiazole and Generation of Persistent Radical Anions

Synthesis and Applications of 5‐Membered Chalcogen‐Nitrogen π‐Heterocycles with Three Heteroatoms

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Supramolecular association of 1,2,5-chalcogenadiazoles: an unexpected self-assembled dissymetric [Se⋯N]2 four-membered ring

Cited by 36 publications

References 14 publications

The N‐Alkylation of Substituted 4‐Tetrazolo[1,5‐a]pyridines: Easy Access to a New Series of Electrophiles

The N‐Alkylation of Substituted 4‐Tetrazolo[1,5‐a]pyridines: Easy Access to a New Series of Electrophiles

[1,2,5]Selenadiazolo[3,4‐b]pyrazines: Synthesis from 3,4‐Diamino‐1,2,5‐selena­diazole and Generation of Persistent Radical Anions

Synthesis and Applications of 5‐Membered Chalcogen‐Nitrogen π‐Heterocycles with Three Heteroatoms

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[1,2,5]Selenadiazolo[3,4‐b]pyrazines: Synthesis from 3,4‐Diamino‐1,2,5‐selenadiazole and Generation of Persistent Radical Anions