Reactivity of Thiophenes, Oligothiophenes and Benzothiophenes

Rajappa, S.; Gumaste, V. K.

doi:10.1016/b978-0-12-404598-9.00001-8

Cited by 17 publications

(7 citation statements)

References 256 publications

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“…Thus, it is interesting to notice the differences in photoreactivity upon varying the connectivity in bithiophenes (2,2′‐bithiophene as in 2 versus 2,3′‐bithiophene as in 1 ) as well as the sites of electrocyclization of thiophene (2‐position in 1 versus 3‐position in 2 ) and fluorene [21] . At this point, one must recall that the photochemical dicyclization of 2,7‐bis(biphen‐2‐yl)fluorene, to yield the corresponding dicyclized product, was unsuccessful [23a,26] . In similar lines, Itami et al reported the oxidative cyclization reaction of 2,2′‐bithiophene moieties (five of them) attached to corannulene core to produce decathia quintuple [6]‐helicene in up to only 20% yield.…”

Section: Resultsmentioning

confidence: 99%

Behaviour of Regioisomeric Bithiophenes in the Oxidative Synthesis of Tetrathieno‐Fused π‐Expanded Fluorenes and Their Characterization

et al. 2020

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Differently-linked bithienyl-attached fluorenes have been synthesized. While the oxidative photodicyclization of 2,3'-bithiophene-containing fluorene was successful to yield tetrathieno-fused regioisomeric π-expanded fluorenes, the reaction with 2,2'-bithiophene-containing fluorene was very sluggish. Interestingly, the connectivity in bithiophenes appears to determine the (photo)reactivity. On the one hand, under mild Scholl conditions, 2,3'-bithiophene-containing fluorene yielded a highly regioselective product while 2,2'bithiophene-containing fluorene led to polymerization. The optical and electrochemical properties of tetrathienoannulated π-expanded fluorenes were investigated, and they were found to be quite different from those of the phenanthrenoannulated π-expanded analogues. These newly obtained sulfur-edged π-expanded fluorenes may hold promise in organic electronics.

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Section: Resultsmentioning

confidence: 99%

Behaviour of Regioisomeric Bithiophenes in the Oxidative Synthesis of Tetrathieno‐Fused π‐Expanded Fluorenes and Their Characterization

et al. 2020

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“…These observations were somewhat surprising, since thiophenic compounds are readily oxidized to their corresponding sulfones in diesel fuels. 33 It was reported that oxidation of thiophenic sulfur in the presence of electron withdrawing groups is difficult, 34 but thianaphthene does not have any substituents. In fact, the preparation of thianaphthene-1,1dioxide from thianaphthene is readily achieved by reaction with hydrogen peroxide in dilute acetic acid.…”

Section: Resultsmentioning

confidence: 99%

Heterocyclic Addition Reactions during Low Temperature Autoxidation

Siddiquee

Klerk

2015

Energy Fuels

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Low temperature air oxidation affects many aspects of the fuels business: weathering, storage stability, hardening, and fouling. Addition reactions taking place during the autoxidation of different heterocyclic compound classes were studied at 130°C. This investigation reports on the conversion, product selectivity, nature of addition products, and plausible mechanisms that would explain the observations subsequent to the oxidation of indole, 2,3-dihydroindole, quinoline, benzofuran, 2,3-dihydrobenzofuran, and thianaphthene. Of these, indole is known to be prone to oxidative addition. Among the five-membered heterocyclic compounds, the propensity to form oxidative addition products increased in the order: S ≪ O < N. Addition took place mainly through C−C bond formation. In comparison to hydrocarbons, it was surprising to find that indole and 2,3-dihydroindole were less prone to oxidative addition than the five-membered naphtheno-aromatic hydrocarbon analogues indene and indan. On the basis of the work, some implications for low temperature oxidation processes, and free radical processes in general, are discussed.

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“…28 Of note, the 3 ILCT state could also undergo electron transfer reactions that are typical of Type I photoprocesses or novel modes that are unique to oligothiophenes. 29 Having shown that 1 and 2 can sensitize 1 O 2 and undergo photosubstitution, their (photo)cytotoxicity was examined in Chart 1. Molecular Structures of Complexes 1 and 2 S1 and S2.…”

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confidence: 99%

“…In principle, the solvated complexes can also absorb photons and participate in subsequent photochemical or photosensitization reactions . Of note, the 3 ILCT state could also undergo electron transfer reactions that are typical of Type I photoprocesses or novel modes that are unique to oligothiophenes …”

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confidence: 99%

Anticancer Agent with Inexplicable Potency in Extreme Hypoxia: Characterizing a Light-Triggered Ruthenium Ubertoxin

et al. 2021

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Tumor hypoxia renders treatments ineffective that are directly (e.g., radiotherapy and photodynamic therapy) or indirectly (e.g., chemotherapy) dependent on tumor oxygenation. This study introduces a ruthenium compound as a light-responsive anticancer agent that is water-soluble, has minimal dark cytotoxicity, is active at concentrations as low as 170 pM in ∼18.5% O2 normoxia and near 10 nM in 1% O2 hypoxia, and exhibits phototherapeutic indices as large as >500,000 in normoxia and >5,800 in 1% O2 hypoxia using broadband visible and monochromatic blue light treatments. These are the largest values reported to date for any compound class. We highlight the response in four different cell lines to improve rigor and reproducibility in the identification of promising clinical candidates.

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Reactivity of Thiophenes, Oligothiophenes and Benzothiophenes

Cited by 17 publications

References 256 publications

Behaviour of Regioisomeric Bithiophenes in the Oxidative Synthesis of Tetrathieno‐Fused π‐Expanded Fluorenes and Their Characterization

Behaviour of Regioisomeric Bithiophenes in the Oxidative Synthesis of Tetrathieno‐Fused π‐Expanded Fluorenes and Their Characterization

Heterocyclic Addition Reactions during Low Temperature Autoxidation

Anticancer Agent with Inexplicable Potency in Extreme Hypoxia: Characterizing a Light-Triggered Ruthenium Ubertoxin

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