On the nucleophilic derivatization of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-<i>c</i>]pyridine: basis for biologically interesting species and building blocks for organic materials

González-Antonio, Oscar; Villalobos, Mauricio Navarro; Vázquez-Alvarado, María Magdalena; Santillán, Rosa; Flores-Pérez, Blas; Romero‐Ávila, Margarita; Farfán, Norberto

doi:10.1039/c9nj01855g

Cited by 4 publications

(12 citation statements)

References 38 publications

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“…Aromatic nucleophilic substitution of 4,7-dibromo [1,2,5]thiadiazolo [3,4-d]pyridazine with thiols led to the formation of 4,7-bis-thiosubstituted [1,2,5]thiadiazolo [3,4-d]pyridazines [4]; all attempts to isolate mono-substituted derivatives were unsuccessful. On the other hand, for the synthesis of 4,7-bis(alkylthio)benzo[c][1,2,5]thiadiazole, Buchwald-Hartwig conditions are required: treatment with alkylthiols and a mixture of Pd 2 (dba) 3 , DPPF, and DIPEA [2].…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, for the synthesis of 4,7-bis(alkylthio)benzo[c][1,2,5]thiadiazole, Buchwald-Hartwig conditions are required: treatment with alkylthiols and a mixture of Pd 2 (dba) 3 , DPPF, and DIPEA [2]. We assumed that the synthesis of 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo [3,4- c]pyridine 1 from 4,7-dibromo- [1,2,5]thiadiazolo [3,4-c]pyridine 2 can proceed smoothly through a combination of the two reactions-nucleophilic substitution and Buchwald-Hartwig cross-coupling.…”

Section: Resultsmentioning

confidence: 99%

“…Bis(alkylsulfanyl) derivatives of heteroaromatic compounds containing long alkyl chain are of interest as compounds with device applications. In particular, 4,7-bis(dodecylthio) [1,2,5]thiadiazolo [3,4-d]pyridazine possesses liquid crystalline properties [1]; 4,7-bis(alkylthio)benzo[c] [1,2,5]thiadiazole has been used as a precursor for discotic liquid crystals for device application in vertical electrode configuration [2]; and octa(alkylthio)substituted zinc phthalocyanines have been used as photosensitizers for photodynamic therapy [3]. The discovery of new 1,2,5-chalcogenadiazoles fused with aromatic and heteroaromatic rings, containing alkylsulfanyl groups with long alkyl chains, is an interesting and important task.…”

Section: Introductionmentioning

confidence: 99%

“…The discovery of new 1,2,5-chalcogenadiazoles fused with aromatic and heteroaromatic rings, containing alkylsulfanyl groups with long alkyl chains, is an interesting and important task. 4,7-Bis(alkylthio) [1,2,5]thiadiazolo [3,4-c]pyridines, according to the Reaxys and SciFinder search, have not been described in the literature. Herein, we report the two-step synthesis of 4,7-bis(dodecylthio)- [1,2,5]thiadiazolo [3,4-…”

Section: Introductionmentioning

confidence: 99%

“…4,7-Bis(alkylthio) [1,2,5]thiadiazolo [3,4-c]pyridines, according to the Reaxys and SciFinder search, have not been described in the literature. Herein, we report the two-step synthesis of 4,7-bis(dodecylthio)- [1,2,5]thiadiazolo [3,4-…”

Section: Introductionmentioning

confidence: 99%

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4,7-Bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine

Chmovzh

Kudryashev

Ракитин

2021

Molbank

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Bis(alkylsulfanyl) derivatives of 1,2,5-thiadiazoles fused with aromatic and heteroaromatic rings containing long alkyl chains are of interest as compounds with liquid crystalline properties. In this communication, 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 was obtained from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 by a combination of two reactions—aromatic nucleophilic substitution SNAr and Buchwald–Hartwig cross-coupling. The structure of the newly synthesized compounds was established by means of elemental analysis; high-resolution mass spectrometry; 1H, 13C NMR, IR and UV spectroscopy; and mass spectrometry.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

4,7-Bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine

Chmovzh

Kudryashev

Ракитин

2021

Molbank

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Tuning of the Coordination and Emission Properties of 4-Amino-2,1,3-Benzothiadiazole by Introduction of Diphenylphosphine Group

Sukhikh

Khisamov

Баширов

et al. 2020

Crystal Growth & Design

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A novel amino-benzothiadiazole bearing diphenylphosphine groups (L) was designed and synthesized. A number of its coordination compounds of Cu(I) (1•0.75C 7 H 8 , 2a,b), Pd(II) (4), and Pt(II) (5) were prepared demonstrating the coordination of L ligand via N and/or P atoms. The reaction with strong Lewis acid Zn(II) resulted in the rearrangement of PNP to P−P−N moiety and formation of complex 3. The structures of L, 2−5 were determined by single crystal X-ray (XRD) diffraction, while that of 1•0.75C 7 H 8 was determined by powder XRD analysis. Intermolecular secondary bonding of S•••S interactions in the compounds, unusual for benzothiadiazoles, was discussed supported by quantum chemical calculations. Differences in the structures of the compounds cause significant changes of photophysical properties. In particular, the position of the electronic absorption band is featured by the conformation of L, viz., the dihedral angle between the benzothiadiazole unit and the PNP moiety, as proved by TD-DFT calculations performed on model molecules. The photophysical properties of the compounds also strongly depend on the coordination mode of L: the presence of a bond between the metal and the N atom of the thiadiazole unit plays an essential role in defining the position of the absorption and emission bands as well as emission lifetime of these compounds. The thermally activated delayed fluorescence and phosphorescence mechanisms in a thermal equilibrium were determined for 1• 0.75C 7 H 8 . Complex 5 features a broad emission band spanning the entire visible region; moreover, it shows an unusual clear-white luminescence, which remains visible even in the daylight.

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Assessing electronic properties of desymmetrized heterocyclic patterns: towards tuning small molecules for photovoltaic applications

et al. 2020

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A series of highly attainable desymmetrized heterocyclic compounds with Donor-Acceptor-Donor-Acceptor-X (D-A-D-X) architectures were synthesized. The structures, where X corresponds to a heteroaromatic portion (pyridine, ferrocene, thiadiazolopyridine), were designed through computational analysis. Molecular geometries for all compounds were studied and parameters of charge transfer were computed in order to analyse the behaviour in each architecture. Spectroscopic properties (maximum absorption wavelengths, extinction coefficients and HOMO-LUMO gaps) were predicted and measured experimentally. UV-Vis absorption profiles and values of HOMO-LUMO optical gaps (in the vicinity of 2.0 eV), together with the computational results, are properties that position the obtained systems, as potential candidates for developing efficient photovoltaic materials based on synthetically accessible small organic molecules.

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On the nucleophilic derivatization of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine: basis for biologically interesting species and building blocks for organic materials

Abstract: Eleven new thiadiazolopyridine-derived building blocks were synthesized through a selective SNAr reaction and the key steps of their reaction mechanism and spectroscopic properties were studied.

Cited by 4 publications

References 38 publications

4,7-Bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine

4,7-Bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine

Tuning of the Coordination and Emission Properties of 4-Amino-2,1,3-Benzothiadiazole by Introduction of Diphenylphosphine Group

Assessing electronic properties of desymmetrized heterocyclic patterns: towards tuning small molecules for photovoltaic applications

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