Organometallic hydride-transfer agents as reductants for organic semiconductor molecules
[Display omitted] •Two classes of organometallic hydride donors are compared.•Hydride donors are compared to corresponding dimeric electron donors.•RuCp*(mesH) is a particularly strong hydride donor.•Crystal structures are reported for metallocenyl organic hydride donors. Both organic hydride donors...
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Published in | Inorganica Chimica Acta Vol. 489; pp. 67 - 77 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Amsterdam
Elsevier B.V
01.04.2019
Elsevier Science Ltd |
Subjects | |
Online Access | Get full text |
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Abstract | [Display omitted]
•Two classes of organometallic hydride donors are compared.•Hydride donors are compared to corresponding dimeric electron donors.•RuCp*(mesH) is a particularly strong hydride donor.•Crystal structures are reported for metallocenyl organic hydride donors.
Both organic hydride donors, DH, and the dimers formed by some organic radicals and by some 19-electron organometallic sandwich compounds, D2, have recently been examined extensively as n-dopants for organic semiconductors. This properties of two classes of organometallic DH derivatives – organic DH derivatives with metallocenyl substituents and species obtained by hydride reduction of 18-electron D+ sandwich cations – are discussed and compared to those of the corresponding D2 molecules. 1,3-Dimethyl-2-metallocenyl-2,3-dihydro-1H-benzo[d]imidazoles, Mc-DMBI-H (Mc = ferrocenyl [Fc], ruthenocenyl [Rc]), and 1,3-dimethyl-2-phenyl-1H-benzo[d]imidazolium tetrakis(3,5-bis(trifluoromethyl))borates, Mc-DMBI+BAr'4– (Mc = Fc, Rc), have recently been reported as intermediates in the synthesis of the dimers (Mc-DMBI)2; here their crystal structures are reported and compared to those of related molecules. The solution reactivity of the Mc-DMBI-H derivatives with a fullerene acceptor is similar to that of purely organic aryl-DMBI-H species. Previously reported (exo-H-η4-pentamethylcyclopentadiene)(η5-cyclopentadienyl)metal complexes, M(exo-H-Cp*H)Cp (M = Rh, Ir) and the new (η5-pentamethylcyclopentadienyl)(η5-1,3,5-trimethylcyclohexa-1,3-dien-5-yl)ruthenium, RuCp*(mesH), have also been examined as potential reductants for organic semiconductors; RuCp*(mesH) is particularly reactive, affording the radical anions of perylene diimide and 6,13-bis(tri(isopropyl)silylethynyl)pentacene. The electrochemistry of DH, D+, and D2 species is compared for the five compounds. Density-functional theory calculations are used to gain insight into the trends in electrochemistry and reactivity. |
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AbstractList | [Display omitted]
•Two classes of organometallic hydride donors are compared.•Hydride donors are compared to corresponding dimeric electron donors.•RuCp*(mesH) is a particularly strong hydride donor.•Crystal structures are reported for metallocenyl organic hydride donors.
Both organic hydride donors, DH, and the dimers formed by some organic radicals and by some 19-electron organometallic sandwich compounds, D2, have recently been examined extensively as n-dopants for organic semiconductors. This properties of two classes of organometallic DH derivatives – organic DH derivatives with metallocenyl substituents and species obtained by hydride reduction of 18-electron D+ sandwich cations – are discussed and compared to those of the corresponding D2 molecules. 1,3-Dimethyl-2-metallocenyl-2,3-dihydro-1H-benzo[d]imidazoles, Mc-DMBI-H (Mc = ferrocenyl [Fc], ruthenocenyl [Rc]), and 1,3-dimethyl-2-phenyl-1H-benzo[d]imidazolium tetrakis(3,5-bis(trifluoromethyl))borates, Mc-DMBI+BAr'4– (Mc = Fc, Rc), have recently been reported as intermediates in the synthesis of the dimers (Mc-DMBI)2; here their crystal structures are reported and compared to those of related molecules. The solution reactivity of the Mc-DMBI-H derivatives with a fullerene acceptor is similar to that of purely organic aryl-DMBI-H species. Previously reported (exo-H-η4-pentamethylcyclopentadiene)(η5-cyclopentadienyl)metal complexes, M(exo-H-Cp*H)Cp (M = Rh, Ir) and the new (η5-pentamethylcyclopentadienyl)(η5-1,3,5-trimethylcyclohexa-1,3-dien-5-yl)ruthenium, RuCp*(mesH), have also been examined as potential reductants for organic semiconductors; RuCp*(mesH) is particularly reactive, affording the radical anions of perylene diimide and 6,13-bis(tri(isopropyl)silylethynyl)pentacene. The electrochemistry of DH, D+, and D2 species is compared for the five compounds. Density-functional theory calculations are used to gain insight into the trends in electrochemistry and reactivity. Both organic hydride donors, DH, and the dimers formed by some organic radicals and by some 19-electron organometallic sandwich compounds, D2, have recently been examined extensively as n-dopants for organic semiconductors. This properties of two classes of organometallic DH derivatives – organic DH derivatives with metallocenyl substituents and species obtained by hydride reduction of 18-electron D+ sandwich cations – are discussed and compared to those of the corresponding D2 molecules. 1,3-Dimethyl-2-metallocenyl-2,3-dihydro-1H-benzo[d]imidazoles, Mc-DMBI-H (Mc = ferrocenyl [Fc], ruthenocenyl [Rc]), and 1,3-dimethyl-2-phenyl-1H-benzo[d]imidazolium tetrakis(3,5-bis(trifluoromethyl))borates, Mc-DMBI+BAr'4– (Mc = Fc, Rc), have recently been reported as intermediates in the synthesis of the dimers (Mc-DMBI)2; here their crystal structures are reported and compared to those of related molecules. The solution reactivity of the Mc-DMBI-H derivatives with a fullerene acceptor is similar to that of purely organic aryl-DMBI-H species. Previously reported (exo-H-η4-pentamethylcyclopentadiene)(η5-cyclopentadienyl)metal complexes, M(exo-H-Cp*H)Cp (M = Rh, Ir) and the new (η5-pentamethylcyclopentadienyl)(η5-1,3,5-trimethylcyclohexa-1,3-dien-5-yl)ruthenium, RuCp*(mesH), have also been examined as potential reductants for organic semiconductors; RuCp*(mesH) is particularly reactive, affording the radical anions of perylene diimide and 6,13-bis(tri(isopropyl)silylethynyl)pentacene. The electrochemistry of DH, D+, and D2 species is compared for the five compounds. Density-functional theory calculations are used to gain insight into the trends in electrochemistry and reactivity. |
Author | Marder, Seth R. Moudgil, Karttikay Timofeeva, Tatiana V. Risko, Chad Barlow, Stephen Zhang, Siyuan Jucov, Evgheni |
Author_xml | – sequence: 1 givenname: Siyuan surname: Zhang fullname: Zhang, Siyuan organization: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400, United States – sequence: 2 givenname: Karttikay surname: Moudgil fullname: Moudgil, Karttikay organization: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400, United States – sequence: 3 givenname: Evgheni surname: Jucov fullname: Jucov, Evgheni organization: Department of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States – sequence: 4 givenname: Chad surname: Risko fullname: Risko, Chad organization: Department of Chemistry and Center for Applied Energy Research (CAER), University of Kentucky, Lexington, KY 40506, United States – sequence: 5 givenname: Tatiana V. surname: Timofeeva fullname: Timofeeva, Tatiana V. organization: Department of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States – sequence: 6 givenname: Seth R. surname: Marder fullname: Marder, Seth R. organization: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400, United States – sequence: 7 givenname: Stephen surname: Barlow fullname: Barlow, Stephen email: stephen.barlow@chemistry.gatech.edu organization: School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400, United States |
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•Two classes of organometallic hydride donors are compared.•Hydride donors are compared to corresponding dimeric electron donors.•RuCp*(mesH)... Both organic hydride donors, DH, and the dimers formed by some organic radicals and by some 19-electron organometallic sandwich compounds, D2, have recently... |
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SubjectTerms | Aromatic compounds Borates Coordination compounds Crystal structure Density functional theory Derivatives Diimide Dimers Electrochemistry Fullerenes Hydride donor Hydrides Iridium Metallocene Organic semiconductors Rhodium Ruthenium Semiconductors |
Title | Organometallic hydride-transfer agents as reductants for organic semiconductor molecules |
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