Bis-arylsulfenyl- and bis-arylselanyl-benzo-2,1,3-thiadiazoles: synthesis and photophysical characterization

Balaguez, Renata A.; Ricordi, Vanessa G.; Duarte, Rodrigo da Costa; Toldo, Josene M.; Santos, Cristtofer M.; Schneider, Paulo H.; Gonçalves, Paulo Fernando Bruno; Rodembusch, Fabiano Severo; Alves, Diego

doi:10.1039/c6ra04157d

Cited by 40 publications

(27 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A higher variation in the dihedral angle between phenyl rings and the BSD core is observed for compounds 3e and 3g . Small variations of geometrical parameters in the S 0 → S 1 transition for bisarylselanyl‐ compared to bisarylsulfenylbenzo‐2,1,3‐thiadiazoles were observed previously . Thus we expect a similar geometry for S 0 and S 1 states of these compounds, with a small internal reorganization energy for the S 0 → S 1 transition.…”

Section: Resultssupporting

confidence: 68%

“…As already observed to chalcogen compounds, this results can probably also be attributed to the nature of the π→π* electronic transition, indicating that these compounds allow better electronic delocalization in the excited state , . The large Stokes shift range (145–160 nm) in the excited state indicates that these chalcogenyl compounds present charge separation, such as an intramolecular charge transfer character in the excited state (ICT state).…”

Section: Resultssupporting

confidence: 64%

“…The calculated absorption wavelengths are shown together with their respective oscillator strength and dipole moments in Table . The weak oscillator strengths presented are due to the lack of planarity of the dyes …”

Section: Resultsmentioning

confidence: 99%

“…Recently, our research group described the synthesis and photophysical characterization of bisarylsulfenyl‐ and bisarylselanylbenzo‐2,1,3‐thiadiazoles ( A and B respectively) via copper‐catalyzed cross‐coupling reaction of arylthiols or diaryl diselenides with the commercially available 4,7‐dibromobenzo[ c ][1,2,5]thiadiazole (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Bisarylselanylbenzo‐2,1,3‐selenadiazoles: Synthesis, Photophysical, Electrochemical and Singlet‐Oxygen‐Generation Properties

et al. 2018

Self Cite

View full text Add to dashboard Cite

We describe herein our results on the synthesis of bisarylselanylbenzo‐2,1,3‐selenadiazoles through double cross‐coupling reaction. The named compounds were obtained in moderate to good yields by reactions of a range of diaryl diselenides with the 4,7‐dibromobenzo[c][1,2,5]selenadiazole using 20 mol‐% of CuO nanoparticles as a catalyst. In addition, the obtained compounds were investigated regarding their photophysical properties in solution and singlet oxygen generation. Bisarylselanylbenzo‐2,1,3‐selenadiazoles presents strong absorption bands at UV region and red emission properties, depending on the substituent. Geometrical, photophysical and electronic properties of the compounds are characterized with density functional theory calculations. In all derivatives are observed the oxidation process of Se atom, using electrochemical analysis. Also, the quantum yields of photosensitized 1O2 production of the synthesized compounds were slightly lower than the standard, but still displays good ability to generate singlet oxygen species. The ability to generate 1O2 of benzo‐2,1,3‐selenadiazole derivatives after being exposed to light and oxygen allowed us to envisage them as a potential application in photodynamic therapy.

show abstract

Section: Resultssupporting

confidence: 68%

Section: Resultssupporting

confidence: 64%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Bisarylselanylbenzo‐2,1,3‐selenadiazoles: Synthesis, Photophysical, Electrochemical and Singlet‐Oxygen‐Generation Properties

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…Organoselenium compounds are attractive synthetic targets because of their selective reactions [38–43], photophysical properties [44–49] and interesting biological activities [50–52]. An interesting class of molecules are the selanyl-1,2,3-triazoles [53–61] which can present some biological applications.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Costa¹,

Seus²,

Roehrs³

et al. 2017

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

The use of sonochemistry is described in the organocatalytic enamine-azide [3 + 2] cycloaddition between 1,3-diketones and aryl azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl azidophenyl selenides, providing an efficient access to new ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones in good to excellent yields and short reaction times. In addition, this protocol was extended to β-keto esters, β-keto amides and α-cyano ketones. Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very mild reaction conditions. 694

show abstract

Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors

Santos

Pereira

Pinz

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

Functionalization of 2,1,3‐benzothiadiazole (BTD) with thiols at C‐5 position remains low explored. Moreover, the arylthiol‐substitutions at this position are also unexplored and can not be found by a SN2 or SN1 reaction. In this sense, herein we present a new palladium‐catalyzed methodology for a wide variety of unpublished 5‐arylsulfanyl‐benzo‐2,1,3‐thiadiazole derivatives synthesis with moderate to high yields using a low catalytic loading of Pd(L‐Pro)2 as low‐coast, and efficient catalyst in low reaction time. Besides, we concluded that the pKa of thiol species has an important role in this catalysis, mainly in the CMD like catalytic cyclo process, which strongly interferes in the reaction yields. Furthermore, arylsulfanyl‐benzo‐2,1,3‐thiadiazoles derivatives have been assessed (in vitro) as potential acetylcholinesterase inhibitors.

show abstract

Bis-arylsulfenyl- and bis-arylselanyl-benzo-2,1,3-thiadiazoles: synthesis and photophysical characterization

Abstract: Bis-arylsulfenyl- and bis-arylselanyl-benzo-2,1,3-thiadiazoles were synthesized in good yields by copper-catalysed cross-coupling reaction of arylthiols or diaryl diselenides with the commercially available 4,7-dibromobenzo[c][1,2,5]thiadiazole.

Cited by 40 publications

References 72 publications

Bisarylselanylbenzo‐2,1,3‐selenadiazoles: Synthesis, Photophysical, Electrochemical and Singlet‐Oxygen‐Generation Properties

Bisarylselanylbenzo‐2,1,3‐selenadiazoles: Synthesis, Photophysical, Electrochemical and Singlet‐Oxygen‐Generation Properties

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Efficient palladium‐catalyzed C‐S cross‐coupling reaction of benzo‐2,1,3‐thiadiazole at C‐5‐position: A potential class of AChE inhibitors

Contact Info

Product

Resources

About