Fluorenyl-substituted silole molecules: geometric, electronic, optical, and device properties
Zhan, Xiaowei1,2,3,4; Haldi, Andreas2,5; Risko, Chad1,2; Chan, Calvin K.6; Zhao, Wei6; Timofeeva, Tatiana V.7; Korlyukov, Aleksander7; Antipin, Mikhail Yu.7; Montgomery, Sarah2,5; Thompson, Evans2,5; An, Zesheng1,2; Domercq, Benoit2,5; Barlow, Stephen1; Kahn, Antoine6; Kippelen, Bernard2,5; Bredas, Jean-Luc1,2; Marder, Seth R.1,2
AbstractA series of silole molecules with fluorenyl substituents at varying positions-1-(9,9-dimethylfluoren-2-yl)-1,2,3,4,5-pentaphenylsilole, 1-(fluoren-9-yl)-1,2,3,4,5-pentaphenylsilole, 1,1,3,4-tetraphenyl-2, 5-bis(9,9-dimethylfluoren-2-yl) silole, and 1,1-diphenyl-2,3,4,5-tetrakis(9,9-dimethylfluoren-2-yl)silole-has been synthesized and compared to the previously reported compounds, 1,1,2,3,4,5-hexaphenylsilole and 1,1-bis(9,9-dimethylfluoren-2-yl)-2,3,4,5-tetraphenylsilole. The effect of fluorenyl substitution pattern on the geometric, thermal, electronic, optical, and electroluminescence properties was investigated both experimentally and theoretically. Analysis of the X-ray crystal packing diagrams for two new fluorenyl-substituted siloles indicates the presence of pi-pi stacking and CH center dot center dot center dot pi interactions in the solid state. Across the series, excellent thermal and morphological stabilities are displayed. Photoelectron/inverse-photoelectron spectroscopy measurements and density functional theory (DFT) calculations suggest that increased conjugation length through substitution at the 2- and 5-positions plays a more significant role in tuning the ionization potentials and electron affinities of these siloles than do inductive effects through substitution of the silicon. The electronic structure (e. g., HOMO-LUMO gap) and, hence, the optical absorption and fluorescence properties are also sensitive to the positions at which the fluorenyl groups are introduced, with substitution at the 2,5-positions having the largest effect. Solution-processed electroluminescent devices fabricated with the fluorenyl-substituted siloles as the emissive layer have luminous efficiencies as high as 3.6 cd A(-1).
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WOS IDWOS:000257125800011
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Document Type期刊论文
Corresponding AuthorZhan, Xiaowei
Affiliation1.Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA
2.Georgia Inst Technol, Ctr Organ Photon & Elect, Atlanta, GA 30332 USA
3.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
4.Chinese Acad Sci, Inst Chem, Key Lab Organ Solids, Beijing 100080, Peoples R China
5.Georgia Inst Technol, Sch Elect & Comp Engn, Atlanta, GA 30332 USA
6.Princeton Univ, Dept Elect Engn, Princeton, NJ 08544 USA
7.New Mexico Highlands Univ, Dept Nat Sci, Las Vegas, NM 87701 USA
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GB/T 7714
Zhan, Xiaowei,Haldi, Andreas,Risko, Chad,et al. Fluorenyl-substituted silole molecules: geometric, electronic, optical, and device properties[J]. JOURNAL OF MATERIALS CHEMISTRY,2008,18(26):3157-3166.
APA Zhan, Xiaowei.,Haldi, Andreas.,Risko, Chad.,Chan, Calvin K..,Zhao, Wei.,...&Marder, Seth R..(2008).Fluorenyl-substituted silole molecules: geometric, electronic, optical, and device properties.JOURNAL OF MATERIALS CHEMISTRY,18(26),3157-3166.
MLA Zhan, Xiaowei,et al."Fluorenyl-substituted silole molecules: geometric, electronic, optical, and device properties".JOURNAL OF MATERIALS CHEMISTRY 18.26(2008):3157-3166.
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