1990
DOI: 10.1039/p29900000931
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Radical cations and anions from some simple polythiophenes: an ESR investigation

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Cited by 53 publications
(30 citation statements)
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“…(close to that of the free electron g 2.0023) indicates little participation of the heterocyclic sulfur atoms in delocalising the unpaired electron, thus reflecting a spin density distribution involving primarily the carbon backbone and analogous to that found for the radical cations of the smaller oligomers and of thiophene itself. [11,33,34] Indeed, Figure in the SOMO of 1…”
Section: Epr and Dft Study Of Radical Ionsmentioning
confidence: 97%
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“…(close to that of the free electron g 2.0023) indicates little participation of the heterocyclic sulfur atoms in delocalising the unpaired electron, thus reflecting a spin density distribution involving primarily the carbon backbone and analogous to that found for the radical cations of the smaller oligomers and of thiophene itself. [11,33,34] Indeed, Figure in the SOMO of 1…”
Section: Epr and Dft Study Of Radical Ionsmentioning
confidence: 97%
“…[3,4,9,10] As a consequence of the lower oxidation potential with respect to that of thiophene, radical cations of longer oligothiophenes can be easily generated by TFA also in the absence of metal ions. [3,11] Radical anions and dianions of alkyl-end-capped bithiophenes are instead unstable, [9] unless the alkyl groups are replaced by trimethylsilyl moieties. [12] Negative ions are more easily accessible in the presence of cyano and [13] nitro groups [14] or in the case of longer end-capped oligothiophenes.…”
mentioning
confidence: 99%
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“…This radical cation had T+ % 1 h. The 5-methoxy derivative of 1,3-benzodioxole (3) even by oxidation by tolyl-TI"' gave the dimer (4) spectrum [aCH, (4 H) = 0.518, aoMe (6 H) = 0.137, aH3'93" (2 H) = 0.105, a H 6 ' p 6 " (2 H) = 0.076 mT; lit.,27 aCHz (4 H) = 0.546, aoMe (6 H) = 0.140, aH6,6' (4 H) = 0.033 mTJ, attesting to the well-known, high propensity for 1,2,4-trialkoxybenzenes to undergo dimerization. 28 The 2,2'-bithiophene radical cation (14a'+) is a reactive species, prone to undergo dimerization to quaterthienyl in trifluoroacetic acid.29 Its EPR spectrum was previously 30 recorded by low-temperature oxidation (irradiation in the presence of Hg" trifluoroacetate) of 2,2'-bithiophene in dichloromethane-trifluoroacetic acid. In HFP, tolyl-TI"' oxidation of 2,2'-bithiophene gave a weak spectrum of a radical cation [aHs9" (2 H) 0.77, a H 4 y 4 ' (2 H) 0.027, a H 3 y 3 ' (2 H) 0.385 mT; lit.,30aH5*5'(2H)0.327,aH4,4'(2 H)0.222, ~" ~, ~' ( 2 H)O.l06mT].…”
Section: Comparison Between Oxidation In Hfp and Other Media In Some ...mentioning
confidence: 99%
“…34 Among these polyheterocycles, thiophene oligomer is a subject of considerable interest due to its simple structure, and these oligomers have been used as models [35][36][37][38][39][40] to study the electronic properties of polythiophene. [41][42][43][44][45][46][47] Therefore, the use of thiophene based molecules is inevitable in the fabrication of materials for solar cells. 48 Recent developments in small molecule organic solar cells (SMOSC) mainly use these conjugated oligomers.…”
Section: Introductionmentioning
confidence: 99%