Tetraazabenzodifluoranthene Diimides: Building Blocks for Solution‐Processable n‐Type Organic Semiconductors

Li, Haiyan; Kim, Felix Sunjoo; Ren, Guoqiang; Hollenbeck, Emily C.; Subramaniyan, Selvam; Jenekhe, Samson A.

doi:10.1002/anie.201210085

Cited by 160 publications

(145 citation statements)

References 43 publications

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“…In their studies on alternative acceptors, Jenekhe and co-workers extensively explored the use of copolymer PSEHTT (Figure 4) as the donor in combination with various different naphthalene diimide derivatives, both polymers [93][94][95][96][97] and small-molecule compounds. [98][99][100] The best PCE of 6.18 % (with a high V oc of 0.92 V) was obtained with dimeric acceptor DBFI-DMT: [100] the authors explain such an excellent performance in terms of the relatively high-lying LUMO of the acceptor coupled with its particular, twisted 3D conformation, which had a positive influence on the bulk charge-transport properties of the photovoltaic devices.…”

Section: Tztz-containing Polymersmentioning

confidence: 91%

Photoactive Compounds Based on the Thiazolo[5,4‐d]thiazole Core and Their Application in Organic and Hybrid Photovoltaics

et al. 2015

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Thiazolo[5,thiazoles (TzTzs) are fused bicyclic heteroaromatic compounds characterized by a rigid planar backbone and an extended π-conjugated electronic structure. Although they have been known for many decades, interest in their properties and applications has begun to increase only recently, after their incorporation into a series of active materials used in the field of organic electronics. Recently, the thi-

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Section: Tztz-containing Polymersmentioning

confidence: 91%

Photoactive Compounds Based on the Thiazolo[5,4‐d]thiazole Core and Their Application in Organic and Hybrid Photovoltaics

et al. 2015

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“…[38][39][40][41][42][43][44][45][46][47] Li et al reported the synthesis of heterocyclic fused fluoranthene derivatives, tetraazabenzodifluoranthne dimides, as potential electron acceptor materials in solar cells. 48 In our earlier report, we have observed very high thermal stability and predominant n-type character for fluoranthene derivatives, bis(4-(7,9,10-triphenylfluoranthen-8-yl)phenyl)sulfane (TPFDPS) and 2,8-bis (7,9,10- 49 We have explored these molecules as electron transport materials for OLEDs using 2-tert-Butyl-9,10-di(naphth-2-yl)anthracene (TBADN) as the active layer, N,N'-diphenyl-N,N'-bis (3-methylphenyl)(1,1'-biphenyl)-4,4'-diamine (TPD) as hole transport layer, in a tri-layer device configuration; and achieved moderate device efficiencies. In this report, we have extended our studies to use modified fluoranthene derivatives as both electron transport as well as light emitting layer for OLEDs, thus simplifying the device architecture by minimizing the number of layers.…”

Section: Introductionmentioning

confidence: 97%

Fluoranthene-Based Molecules as Electron Transport and Blue Fluorescent Materials for Organic Light-Emitting Diodes

Kumar

Patil

2015

J. Phys. Chem. C

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Herein, we report the synthesis, characterization and potential application of bis(4-(7,9,10-triphenylfluoranthen-8-yl)phenyl)sulfone (TPFDPSO2) and 2,8-bis(7,9,10-triphenylfluoranthen-8-yl)dibenzo[b,d]thiophene 5,5-dioxide (TPFDBTO2) as electron transport as well as light emitting materials. These fluoranthene derivatives were synthesized by oxidation of their corresponding parent sulphide compounds which were prepared via Diels-Alder reaction. These materials exhibit deep blue fluorescence emission in both solution and thin film, high PLQY, thermal and electrochemical stability over a wide potential range. Hole-only and electron-only devices were fabricated to study the charge transport characteristics and predominant electron transport property comparable with well-known electron transport material, Alq 3 , was observed. Further, bilayer electroluminescent devices were fabricated utilizing these fluoranthene derivatives as electron transport as well as emitting layer and device performance was compared with their parent sulphide molecules. The EL devices fabricated with these molecules displayed bright sky blue color emission and 5-fold improvement in EQE with respect to their parent compounds.

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“…[9] Acenaphthene-5,6-dicarboxyic anhydride 7 was prepared from acenaphthene using reported procedure. [10] Synthesis N-(2-Ethylhexyl)-acenaphthene-5,6-dicarboxyimide (8a) [10] A solution of 7 (3.36 g, 15 mmol) and 2-ethylhexylamine (3.7 mL, 23 mmol) in ethanol (80 mL) was heated at reflux for 12 h. After cooling at rt, the solvent was evaporated under reduced pressure. …”

Section: Methodsmentioning

confidence: 99%

“…[10] The Diels-Alder reactions of 1a with 2,5-diphenylthiophene 1,1-dioxide (9) [11] and tetracyclone 10 were examined; the reaction mixtures of 1a and the dienes in o-xylene were heated at reflux for 24 h. Under the reaction conditions, subsequent aromatization occurred to form 2a and 3a as yelow crystals in 10% and 22% yields, respectively (Scheme 3a). The reaction of 1b with α,α'-dibromo-o-xylylene [12] generated by reductive debromination of α,α,α',α'-tetrabromo-o-xylene 11…”

Section: Synthesis Of π-Extended Fluoranthene Imidesmentioning

confidence: 99%

π-Extended fluoranthene imide derivatives: synthesis, structures, and electronic and optical properties

et al. 2017

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Diels–Alder reactions of acenaphthylene-5,6-dicarboximide (AI) derivatives with the corresponding dienes afforded some derivatives of π-extended fluoranthene imide, namely N-(2-ethylhexyl)-7,10-diphenylfluoranthene imide (DPFI) and N-(2-ethylhexyl)-7,8,9,10-tetraphenylfluoranthene imide (TPFI), N-(n-octyl)-benzo[k]fluoranthene imide (BFI), and N-(n-octyl)-naphtho[k]fluoranthene imide (NFI). Molecular structures of TPFI and BFI reveal that the core π-skeletons have a highly planar structure, and the molecules form a dimeric structure in the crystals. The absorption spectra exhibit bathochromic shift with π-extension of the core π-skeletons. On the other hand, DPFI and TPFI show the long-wavelength emission related to BFI, probably due to π-extension toward the phenyl substituents in the excited states. BFI and NFI exhibited an interesting concentration-dependent 1H-NMR behavior in CDCl3, suggesting self-aggregation formation. Moreover, BFI and NFI show moderate and remarkable solvatofluorochromism in solutions (BFI for ΔλEM = 67 nm, NFI for ΔλEM = 116 nm), respectively, while DPFI and TPFI show weak solvatofluorochromism. The density functional theory calculations demonstrate that the considerable spatial separation between the HOMO and LUMO coefficients in the NFI molecule. The result indicates that the ground-to-excited state transition of NFI should have intramolecular charge transfer (ICT) character.

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Tetraazabenzodifluoranthene Diimides: Building Blocks for Solution‐Processable n‐Type Organic Semiconductors

Cited by 160 publications

References 43 publications

Photoactive Compounds Based on the Thiazolo[5,4‐d]thiazole Core and Their Application in Organic and Hybrid Photovoltaics

Photoactive Compounds Based on the Thiazolo[5,4‐d]thiazole Core and Their Application in Organic and Hybrid Photovoltaics

Fluoranthene-Based Molecules as Electron Transport and Blue Fluorescent Materials for Organic Light-Emitting Diodes

π-Extended fluoranthene imide derivatives: synthesis, structures, and electronic and optical properties

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