Energy-level structure and carrier transport in the poly(<i>N</i>-vinyl carbazole): trinitrofluorenone charge-transfer complex

Mort, J.; Emerald, R. L.

doi:10.1063/1.1662954

Cited by 30 publications

(3 citation statements)

References 10 publications

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“…Charge hopping between CT complexes has been known to occur in some doped molecular systems. [65] Further studies are needed to address the plausibility of this mechanism for MDMO-PPV:PCBM blends.…”

Section: Mechanism For Hole-mobility Enhancementmentioning

confidence: 99%

Ambipolar Charge Transport in Films of Methanofullerene and Poly(phenylenevinylene)/Methanofullerene Blends

et al. 2005

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Herein, we report experimental studies of electron and hole transport in thin films of [6,6]‐phenyl C61 butyric acid methyl ester (PCBM) and in blends of poly[2‐methoxy‐5‐(3′,7′‐dimethyloctyloxy)‐1,4‐phenylenevinylene] (MDMO‐PPV) with PCBM. The low‐field hole mobility in pristine MDMO‐PPV is of the order of 10–7 cm2 V–1 s–1, in agreement with previous studies, whereas the electron mobility in pristine PCBM was found by current‐density–voltage (J–V) measurements to be of the order of 10–2 cm2 V–1 s–1, which is about one order of magnitude greater than previously reported. Adding PCBM to the blend increases both electron and hole mobilities, compared to the pristine polymer, and results in less dispersive hole transport. The hole mobility in a blend containing 67 wt.‐% PCBM is at least two orders of magnitude greater than in the pristine polymer. This result is independent of measurement technique and film thickness, indicating a true bulk property of the material. We therefore propose that PCBM may assist hole transport in the blend, either by participating in hole transport or by changing the polymer‐chain packing to enhance hole mobility. Time‐of‐flight mobility measurements of PCBM dispersed in a polystyrene matrix yield electron and hole mobilities of similar magnitude and relatively non‐dispersive transport. To the best of our knowledge, this is the first report of hole transport in a methanofullerene. We discuss the conditions under which hole transport in the fullerene phase of a polymer/fullerene blend may be expected. The relevance to photovoltaic device function is also discussed.

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Section: Mechanism For Hole-mobility Enhancementmentioning

confidence: 99%

Ambipolar Charge Transport in Films of Methanofullerene and Poly(phenylenevinylene)/Methanofullerene Blends

et al. 2005

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“…These molecules readily form charge-transfer complexes with electron donors (1-3) and have been extensively employed as photosensitizers and active constituents of photosensitive composites (4)(5)(6)(7). Of this class of acceptors, 2,4,7-trinitrofluoren-9-one 1 (TNF) appears to be the most investigated molecule, presumably because of its relatively strong n-acid strength as well as its efficient photosensitization effect and electron transport capability (6,7). Unfortunately, TNF has low solubility in organic solvents and exhibits poor compatibility with common matrix polymers; many applications requiring high concentrations of TNF cannot therefore be fulfilled.…”

mentioning

confidence: 99%

Synthesis, molecular and electron transport properties of 2-alkyltrinitrofluoren-9-ones

Ong¹,

Keoshkerian²,

Martin³

et al. 1985

Can. J. Chem.

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2-Alkyltrinitrofluoren-9-ones 2 were conveniently synthesized by controlled nitration of 2-alkylfluoren-9-ones 5 with a mixture of red fuming HNO3 and concentrated H2SO4 at 0–25 °C. The precursors 5 were derived from the corresponding 2-acylfluorenes by appropriate reduction of the acyl function, followed by base-catalysed O2-oxidation at the C-9 position. The regiochemistry of nitration was interesting: with a sterically bulky substituent in 5, nitration occurred at C-4, -5, and -7 positions, affording 2-alkyl-4,5,7-trinitrofluoren-9-one in over 35% yield; on the other hand, 5 with a primary alkyl function underwent nitration predominantly at C-3, -5, and -7 positions. By virtue of its alkyl function, 2-alkyltrinitrofluoren-9-one 2 displayed better solubility and polymer compatibility characteristics than its non-alkylated analog, TNF. However, the charge transfer interactions of 2 with electron donors were weaker than those of TNF, despite the fact that they both have the same electron affinity. Both 2 and TNF exhibited good electron transport properties in poly(N-vinylcarbazole) matrices.

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“…As interesting feature, the spectral zone of photoconductivity of the carbazole-containing polymers can be selected by the appropriate choice of the push–pull molecule. By comparing the electron mobilities of 23 – 26 with that of the reference 2,4,7-trinitrofluoren-9-one, comparable transport properties could be determined [45,46,47,48], demonstrating the pertinence of the strategy for the design of photoconductive materials with poly(nitro)fluorene derivatives.…”

Section: Push–pull Molecules Based On the Connection Of Strong Elementioning

confidence: 99%

Recent Advances on Nitrofluorene Derivatives: Versatile Electron Acceptors to Create Dyes Absorbing from the Visible to the Near and Far Infrared Region

Noirbent

Dumur

2018

Materials

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Push–pull dyes absorbing in the visible range have been extensively studied so that a variety of structures have already been synthesized and reported in the literature. Conversely, dyes absorbing in the near and far infrared region are more scarce and this particularity relies on the following points: difficulty of purification, presence of side-reaction during synthesis, low availability of starting materials, and low reaction yields. Over the years, several strategies such as the elongation of the π-conjugated spacer or the improvement of the electron-donating and accepting ability of both donors and acceptors connected via a conjugated or an aliphatic spacer have been examined to red-shift the absorption spectra of well-established visible dyes. However, this strategy is not sufficient, and the shift often remains limited. A promising alternative consists in identifying a molecule further used as an electron-accepting group and already presenting an absorption band in the near infrared region and to capitalize on its absorption to design near and far infrared absorbing dyes. This is the case with poly(nitro)fluorenes that already exhibit such a contribution in the near infrared region. In this review, an overview of the different dyes elaborated with poly(nitro)fluorenes is presented. The different applications where these different dyes have been used are also detailed.

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Energy-level structure and carrier transport in the poly(N-vinyl carbazole): trinitrofluorenone charge-transfer complex

Cited by 30 publications

References 10 publications

Ambipolar Charge Transport in Films of Methanofullerene and Poly(phenylenevinylene)/Methanofullerene Blends

Ambipolar Charge Transport in Films of Methanofullerene and Poly(phenylenevinylene)/Methanofullerene Blends

Synthesis, molecular and electron transport properties of 2-alkyltrinitrofluoren-9-ones

Recent Advances on Nitrofluorene Derivatives: Versatile Electron Acceptors to Create Dyes Absorbing from the Visible to the Near and Far Infrared Region

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