Synthesis and high hole mobility of isotactic poly(2-N-carbazolylethyl acrylate)

Uryu, Toshiyuki; Ohkawa, Hiroyuki; Oshima, Ryuji

doi:10.1021/ma00170a002

Cited by 57 publications

(58 citation statements)

References 5 publications

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“…The synthesis of A C H T U N G T R E N N U N G (3,4,5)12F8G1-2EOTNF (A8) was reported previously. [8a] This dendron is derived from the first-generation semifluoriFigure 1.…”

Section: Resultsmentioning

confidence: 99%

“…Scheme 1 outlines the synthesis of five new dendrons attached to electron-acceptor molecules based on the dendron 1. The synthesis, which incorporates an aminothienyldioxocyanopyridine (ATOP) moiety at the apex, A C H T U N G T R E N N U N G (3,4,5)12F8G1-PrATOP (A1), was achieved by N,N-dimethylcyclohexylcarbodiimide (DCC)/4-dimethylaminopyridinium-p-toluenesulfonate (DPTS) mediated esterification of 1 with ATOP [18] derivative 2 in 40 % yield. In view of the cyanine type p-conjugated chromophore of ATOP derivatives, dendron A1 is expected to be of interest for its potential photorefractive properties.…”

Section: Resultsmentioning

confidence: 99%

“…[8a] The commercially available naphthalic anhydride (6) and 4-nitronaphthalic anhydride (7) were reacted with 2-(2-aminohydroxy)ethanol to produce imides 9 and 10, respectively, in moderate yields. DCC/DPTS-mediated esterification of 1 with the hydroxyterminated naphthylimide derivatives 9 and 10 produced A C H T U N G T R E N N U N G (3,4,5)12F8G1-2EONpI (A3) and A C H T U N G T R E N N U N G (3,4,5)12F8G1-2EONNpI (A4), respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Single-crystal organic conductors have high charge-carrier mobilities but are usually impractical, [2] whereas conducting polymers have good processability but low charge-carrier mobility. [1,3] Electrically conducting hexagonal columnar liquid crystals (LC) exhibit mobilities approaching those of single crystals. [4] Moreover, the LC phase allows the dynamic reorganization that is necessary for defect repair, and also facilitates the processing of single crystal LC monodomains of organic thin films that are not accessible from organic single crystals.…”

Section: Introductionmentioning

confidence: 99%

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Self‐Assembly of Semifluorinated Minidendrons Attached to Electron‐Acceptor Groups into Pyramidal Columns

Percéc

Aqad

Peterca

et al. 2007

Chemistry A European J

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The synthesis and self-assembly of twelve semifluorinated first-generation dendrons or minidendrons attached to electron-acceptor (n-type) groups generated from various combinations of eight acceptors and three dendrons are reported. Dendrons attached to small electron-acceptor molecules mediate their self-assembly into pi-stacks located in the center of a supramolecular helical pyramidal column with the long axis of the acceptor perpendicular to the long axis of the column. Dendrons attached to large electron-acceptor molecules, such as perylene bisimide, mediate the assembly of their acceptors in an unprecedented arrangement of pi-stacks that have the long axis of the acceptors parallel to the long axis of the supramolecular pyramidal column. All supramolecular columns self-organize into various periodic columnar arrays that exhibit liquid-crystalline phases, crystalline phases, or a liquid-crystalline phase with enhanced intracolumnar order. The present study demonstrates the simplicity and the versatility of the concept of assembly of n-type electroactive groups mediated by semifluorinated dendrons and assesses the scope and limitations of this supramolecular strategy.

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“…The synthesis of A C H T U N G T R E N N U N G (3,4,5)12F8G1-2EOTNF (A8) was reported previously. [8a] This dendron is derived from the first-generation semifluoriFigure 1.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Self‐Assembly of Semifluorinated Minidendrons Attached to Electron‐Acceptor Groups into Pyramidal Columns

Percéc

Aqad

Peterca

et al. 2007

Chemistry A European J

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“…On the other hand, Uryu et al reported that i-PCA had only the monomeric component in its fluorescence spectrum, and it showed 30 times higher mobility than PVK. 11 Taking into account that the excimer sites were known to act as trapping sites for carrier transport in PVK, 15 the result of i-PCA was reasonable. This suggests that the mobility for PCLG is considerably affected by the conformation of carbazolyl groups and the distribution of its related traps.…”

Section: Resultsmentioning

confidence: 93%

Charge transport properties for carbazolyl groups pendant poly(glutamate)

Yoshida

Mitsui

Kawai

et al. 1999

J. Polym. Sci. B Polym. Phys.

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Carbazolyl groups pendant poly(glutamate) (PCLG) was prepared to analyze its charge‐transport properties by employing mobility measurements and thermally‐stimulated current (TSC) measurements. The mobility induced TSC (MITSC) model proposed by I.Chen was employed to evaluate the experimental TSC spectra with mobility results. Simulated MITSC spectra showed good agreement in its peak temperature with experimental TSC spectra for PCLG. This suggests that the carrier transport followed the trap‐limited mechanism estimated by the mobility results. Further, the peaks in experimental TSC spectra appeared over the same temperature range as that in thermally‐stimulated polarization current (TSPC) spectra. Since the TSPC spectra were found to be correlated with the dielectric tan δ spectra for PCLG, the peaks in TSPC spectra are attributed to the side‐chain relaxation for PCLG. Therefore, the similarity between TSPC and TSC spectra indicates that the charge‐transport mechanism for PCLG was considerably affected by side‐chain relaxation for PCLG, which would vary the energy state of trap sites and effectively reduces the energy for the release of the carriers trapped on the illuminated surface. © 1999 John Wiley & Sons, Inc. J Polym Sci B: Polym Phys 37: 61–69, 1999

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Hole mobilities in sol-gel materials

Morais

Chaput

Boilot

et al. 2000

Adv. Mater. Opt. Electron.

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New silylated precursors with hole transporting units are prepared by modification of different active molecules (carbazole, oxadiazole and tetraphenylphenylenediamine derivatives) using sol‐gel precursors. Absorption and photoluminescence spectra show that the electronic structures are not significantly modified by the functionalization. Field dependence of the hole mobility of the different sol‐gel layers is measured using the time‐of‐flight technique. The highest hole mobility is observed for the layer having tetraphenylphenylenediamine units: 5.7 × 10—5 cm2.V—1.s—1 at a field strength of E = 5 × 105 V.cm—1. For the best carbazole compound, the mobility is found to be about twentyfold lower at the same field. Further experiments are required to test these new materials as hole transporting layers in photorefractive and electroluminescent devices. Copyright © 2000 John Wiley & Sons, Ltd.

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Synthesis and high hole mobility of isotactic poly(2-N-carbazolylethyl acrylate)

Cited by 57 publications

References 5 publications

Self‐Assembly of Semifluorinated Minidendrons Attached to Electron‐Acceptor Groups into Pyramidal Columns

Self‐Assembly of Semifluorinated Minidendrons Attached to Electron‐Acceptor Groups into Pyramidal Columns

Charge transport properties for carbazolyl groups pendant poly(glutamate)

Hole mobilities in sol-gel materials

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