Oxidation of End-Capped Pentathienoacenes and Characterization of Their Radical Cations
dc.contributor.author | Malavé, Reyes | en_US |
dc.contributor.author | Ruiz Delgado, M. carmen | en_US |
dc.contributor.author | Hernández, Víctor | en_US |
dc.contributor.author | López navarrete, Juan | en_US |
dc.contributor.author | Vercelli, Barbara | en_US |
dc.contributor.author | Zotti, Gianni | en_US |
dc.contributor.author | Novoa, Juan | en_US |
dc.contributor.author | Suzuki, Yoshitake | en_US |
dc.contributor.author | Yamaguchi, Shigehiro | en_US |
dc.contributor.author | Henssler, John T. | en_US |
dc.contributor.author | Matzger, Adam J. | en_US |
dc.date.accessioned | 2009-11-30T16:44:07Z | |
dc.date.available | 2010-03-01T21:10:28Z | en_US |
dc.date.issued | 2009-11-16 | en_US |
dc.identifier.citation | MalavÉ 14Osuna, Reyes; Ruiz 14Delgado, M. 14Carmen; HernÁndez, VÍctor; LÓpez 14Navarrete, Juan 14T.; Vercelli, Barbara; Zotti, Gianni; Novoa, Juan 14J.; Suzuki, Yoshitake; Yamaguchi, Shigehiro; Henssler, John 14T.; Matzger, Adam 14J. (2009). "Oxidation of End-Capped Pentathienoacenes and Characterization of Their Radical Cations." Chemistry - A European Journal 15(45): 12346-12361. <http://hdl.handle.net/2027.42/64441> | en_US |
dc.identifier.issn | 0947-6539 | en_US |
dc.identifier.issn | 1521-3765 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/64441 | |
dc.identifier.uri | http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=retrieve&db=pubmed&list_uids=19806614&dopt=citation | en_US |
dc.description.abstract | A detailed investigation of the optical and electrochemical properties of two pentathienoacene derivatives, 2,6-bis(trimethylsilyl)-Α-pentathienoacene ( TMS-T5-TMS ) and 2,6-bis(triisopropylsilyl)-Α-pentathienoacene ( TIPS-T5-TIPS ), as the neutral and oxidized species was performed in the temperature range of 80–300 14K. The experimental solution UV/Vis and solid-state Raman spectra were interpreted by using time-dependent DFT and DFT quantum chemical calculations at the B3LYP/6-31G** level. Bond lengths, HOMO–LUMO positions, and charge distribution were also predicted by computational methods for both the neutral and oxidized states of each thienoacene. As evidenced by ESR and spectroelectrochemical data, upon oxidation the pentathienoacene derivative with the less sterically hindering trimethylsilyl solubilizing groups, TMS-T5-TMS , undergoes Π 14dimerization to form [ TMS-T5-TMS ] 2 2+ . In contrast, TIPS-T5-TIPS , with the more bulky triisopropylsilyl solubilizing groups, was oxidized to the radical cation but dimerization was prevented due to steric interactions. These experimental observations are supported by DFT calculations, which were used to investigate [ TMS-T5-TMS ] 2 2+ and [ TIPS-T5-TIPS ] 2 2+ Π 14dimers in the solid state and in solution. The redox potentials and absorption peak locations corresponding to the radical cations and Π 14dimer of TMS-T5-TMS were identified experimentally. | en_US |
dc.format.extent | 377217 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.publisher | WILEY-VCH Verlag | en_US |
dc.subject.other | Chemistry | en_US |
dc.subject.other | General Chemistry | en_US |
dc.title | Oxidation of End-Capped Pentathienoacenes and Characterization of Their Radical Cations | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Departamento de QuÍmica FÍsica, Universidad de MÁlaga, 29071 MÁlaga (Spain), Fax: (+34) 952 132000 | en_US |
dc.contributor.affiliationum | Departamento de QuÍmica FÍsica, Universidad de MÁlaga, 29071 MÁlaga (Spain), Fax: (+34) 952 132000 | en_US |
dc.contributor.affiliationum | Institute for Energetics and Interphases–IENI CNR, C.so Stati Uniti 4, 35127 Padova (Italy), Fax: (+39) 049 8295853 | en_US |
dc.contributor.affiliationum | Department of Chemistry and Macromolecular Science and Engineering Program, University of Michigan, 930 North University, Ann Arbor, MI 48109-1055 (USA) | en_US |
dc.contributor.affiliationum | Department of Chemistry and Macromolecular Science and Engineering Program, University of Michigan, 930 North University, Ann Arbor, MI 48109-1055 (USA) | en_US |
dc.contributor.affiliationother | Departamento de QuÍmica FÍsica, Universidad de MÁlaga, 29071 MÁlaga (Spain), Fax: (+34) 952 132000 | en_US |
dc.contributor.affiliationother | Departamento de QuÍmica FÍsica, Universidad de MÁlaga, 29071 MÁlaga (Spain), Fax: (+34) 952 132000 ; Current address: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400 (USA) | en_US |
dc.contributor.affiliationother | Institute for Energetics and Interphases–IENI CNR, C.so Stati Uniti 4, 35127 Padova (Italy), Fax: (+39) 049 8295853 | en_US |
dc.contributor.affiliationother | Departament de QuÍmica FÍsica and IQTCUB, Facultad de QuÍmica, Universitat de Barcelona, Av. Diagonal 647, 08028 Barcelona (Spain) | en_US |
dc.contributor.affiliationother | Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602 (Japan) | en_US |
dc.contributor.affiliationother | Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602 (Japan) | en_US |
dc.identifier.pmid | 19806614 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/64441/1/chem_200900246_sm_miscellaneous_information.pdf | |
dc.identifier.doi | 10.1002/chem.200900246 | en_US |
dc.identifier.source | Chemistry - A European Journal | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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