Electrochemistry and Electrogenerated Chemiluminescence of Thiophene and Fluorene Oligomers. Benzoyl Peroxide as a Coreactant for Oligomerization of Thiophene Dimers

dc.contributor.utaustinauthorNepomnyashchii, Alexander B.en_US
dc.contributor.utaustinauthorOno, Robert J.en_US
dc.contributor.utaustinauthorLyons, Dani M.en_US
dc.contributor.utaustinauthorBielawski, Christopher W.en_US
dc.contributor.utaustinauthorSessler, Jonathan L.en_US
dc.contributor.utaustinauthorBard, Allen J.en_US
dc.creatorNepomnyashchii, Alexander B.en_US
dc.creatorOno, Robert J.en_US
dc.creatorLyons, Dani M.en_US
dc.creatorBielawski, Christopher W.en_US
dc.creatorSessler, Jonathan L.en_US
dc.creatorBard, Allen J.en_US
dc.date.accessioned2016-09-23T18:04:58Z
dc.date.available2016-09-23T18:04:58Z
dc.date.issued2012-05en_US
dc.description.abstractThe electrochemical properties of oligomers of thiophene (with number of monomer units, n, from 2 to 12) and fluorene (n = 3 to 7) were investigated. Both sets of oligomers were characterized by the presence of two oxidation and two reduction waves as determined by cyclic voltammetry (CV), with the reversibility of the waves depending on the structural properties of the compounds. The addition or removal of a third electron was found to be difficult relative to the second, a finding shown for conjugated oligomers with chain lengths up to 7 in the case of the fluorenes and up to 12 for the thiophenes. The oligothiophenes showed a larger separation between the electrochemical waves for the same chain length, and also substantial electrogenerated chemiluminescence (ECL) signals, whose intensity increased with oligomer size. In contrast, the ECL intensity of the fluorene oligomers was essentially independent of chain length. The ECL spectra for the thiophene dodecamer were obtained with concentrations as low as 20 pM, a result that reflects a high ECL efficiency, close to that of the well-known ECL standard Ru(bpy)(3)(2+). Oligomers were also formed on electrochemical reduction of an appropriately functionalized dimer in the presence of benzoyl peroxide producing a longer wavelength emission (maximum at similar to 540 nm) as opposed to the spectrum of the dimer (lambda(em) = 390 nm).en_US
dc.description.departmentChemistryen_US
dc.description.sponsorshipDepartment of Energy (DOE)en_US
dc.description.sponsorshipRobert A. Welch Foundation F-0021, F-1018, F-1621en_US
dc.description.sponsorshipNational Science Foundation CHE-01057904en_US
dc.identifierdoi:10.15781/T2B27PS41
dc.identifier.citationNepomnyashchii, Alexander B., Robert J. Ono, Dani M. Lyons, Christopher W. Bielawski, Jonathan L. Sessler, and Allen J. Bard. "Electrochemistry and electrogenerated chemiluminescence of thiophene and fluorene oligomers. Benzoyl peroxide as a coreactant for oligomerization of thiophene dimers." Chemical Science 3, no. 8 (May, 2012): 2628-2638.en_US
dc.identifier.doi10.1039/c2sc20263hen_US
dc.identifier.issn2041-6520en_US
dc.identifier.urihttp://hdl.handle.net/2152/41030
dc.language.isoEnglishen_US
dc.relation.ispartofen_US
dc.relation.ispartofserialChemical Scienceen_US
dc.rightsAdministrative deposit of works to Texas ScholarWorks: This works author(s) is or was a University faculty member, student or staff member; this article is already available through open access or the publisher allows a PDF version of the article to be freely posted online. The library makes the deposit as a matter of fair use (for scholarly, educational, and research purposes), and to preserve the work and further secure public access to the works of the University.en_US
dc.rights.restrictionOpenen_US
dc.subjectoligothiophene cation radicalsen_US
dc.subjectfinite-difference algorithmen_US
dc.subjectchain-length dependenceen_US
dc.subjectconjugated polymersen_US
dc.subjectconducting polymersen_US
dc.subjectelectronic-propertiesen_US
dc.subjectsubstituted oligothiophenesen_US
dc.subjectisomerizationen_US
dc.subjectbarriersen_US
dc.subjectrotating-disken_US
dc.subjectderivativesen_US
dc.subjectchemistry, multidisciplinaryen_US
dc.titleElectrochemistry and Electrogenerated Chemiluminescence of Thiophene and Fluorene Oligomers. Benzoyl Peroxide as a Coreactant for Oligomerization of Thiophene Dimersen_US
dc.typeArticleen_US

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