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Guo S, Mohapatra SK, Romanov A, et al. n-Doping of organic electronic materials using air-stable organometallics: a mechanistic study of reduction by dimeric sandwich compounds. Chemistry. 2012;18(46):14760-72doi: 10.1002/chem.201202591.
Guo, S., Mohapatra, S. K., Romanov, A., Timofeeva, T. V., Hardcastle, K. I., Yesudas, K., Risko, C., Brédas, J. L., Marder, S. R., & Barlow, S. (2012). n-Doping of organic electronic materials using air-stable organometallics: a mechanistic study of reduction by dimeric sandwich compounds. Chemistry (Weinheim an der Bergstrasse, Germany), 18(46), 14760-72. https://doi.org/10.1002/chem.201202591
Guo, Song, et al. "n-Doping of organic electronic materials using air-stable organometallics: a mechanistic study of reduction by dimeric sandwich compounds." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,46 (2012): 14760-72. doi: https://doi.org/10.1002/chem.201202591
Guo S, Mohapatra SK, Romanov A, Timofeeva TV, Hardcastle KI, Yesudas K, Risko C, Brédas JL, Marder SR, Barlow S. n-Doping of organic electronic materials using air-stable organometallics: a mechanistic study of reduction by dimeric sandwich compounds. Chemistry. 2012 Nov 12;18(46):14760-72. doi: 10.1002/chem.201202591. Epub 2012 Oct 25. PMID: 23108797.
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Chemistry. 2012 Nov 12;18(46):14760-72. doi: 10.1002/chem.201202591. Epub 2012 Oct 25.

n-Doping of organic electronic materials using air-stable organometallics: a mechanistic study of reduction by dimeric sandwich compounds.

Chemistry (Weinheim an der Bergstrasse, Germany)

Song Guo, Swagat K Mohapatra, Alexander Romanov, Tatiana V Timofeeva, Kenneth I Hardcastle, Kada Yesudas, Chad Risko, Jean-Luc Brédas, Seth R Marder, Stephen Barlow

Affiliations

  1. School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, 30332-0400, USA.

PMID: 23108797 DOI: 10.1002/chem.201202591

Abstract

Several 19-electron sandwich compounds are known to exist as "2×18-electron" dimers. Recently it has been shown that, despite their air stability in the solid state, some of these dimers act as powerful reductants when co-deposited from either the gas phase or from solution and that this behavior can be useful in n-doping materials for organic electronics, including compounds with moderate electron affinities, such as 6,13-bis[tri(isopropyl)silylethynyl]pentacene (3). This paper addresses the mechanisms by which the dimers of 1,2,3,4,5-pentamethylrhodocene (1 b(2)), (pentamethylcyclopentadienyl)(1,3,5-trialkylbenzene)ruthenium (alkyl=Me, 2 a(2); alkyl=Et, 2 b(2)), and (pentamethylcyclopentadienyl)(benzene)iron (2 c(2)) react with 3 in solution. Vis/NIR and NMR spectroscopy, and X-ray crystallography indicate that the products of these solution reactions are 3(·-) salts of the monomeric sandwich cations. Vis/NIR kinetic studies for the Group 8 dimers are consistent with a mechanism whereby an endergonic electron transfer from the dimer to 3 is followed by rapid cleavage of the dimer cation. NMR crossover experiments with partially deuterated derivatives suggest that the C-C bond in the 1 b(2) dimer is much more readily broken than that in 2 a(2); consistent with this observation, Vis/NIR kinetic measurements suggest that the solution reduction of 3 by 1 b(2) can occur by both the mechanism established for the Group 8 species and by a mechanism in which an endergonic dissociation of the dimer is followed by rapid electron transfer from monomeric 1 b to 3.

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