Synthesis and Hole Transport Properties of Highly Soluble Pyrene-Based Discotic Liquid Crystals with Trialkylsilylethynyl Groups

Hirose, Takuji; Shibano, Yuji; Miyazaki, Yutaro; Sogoshi, Norihito; Nakabayashi, Seiichiro; Yasutake, Mikio

doi:10.1080/15421406.2011.536485

Cited by 10 publications

(7 citation statements)

References 28 publications

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“…In a Col phase, LC molecules pile up, and the average molecular distance in a column has been estimated to be around 3.5–5.0 Å . In fact, as shown in Supporting Information Tables S1 and S3, the intermolecular distances of columnar TPC1 n and TPC2 n ( TPC s) were estimated to range from about 4.1 to 4.6 Å.…”

Section: Resultsmentioning

confidence: 99%

“…We have worked on the development of several discotic LCs and studied their thermal, mesomorphic, and charge transport properties . Considering the structural features and the applicability of the columnar LCs, the next challenge is to fix the oriented discotic molecules in the structure and enhance their properties as reported previously .…”

Section: Inrtroductionmentioning

confidence: 99%

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Polymeric fibers and microporous films by photo‐crosslinking of triphenylene‐derived liquid crystals

Hirose

Kikuchi

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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Two series of photoreactive discotic liquid crystals consisting of a triphenylene core and six cinnamate units with one (TPC1 n) or two (TPC2 n) n‐alkoxy groups (C nH2n+1O; n = 10–14), respectively, as peripheral groups are synthesized. Both of them are polymerized into fibers up to 2 mm long by UV irradiation in liquid paraffin in the columnar LC temperature ranges. The fiber structures seem to be preconstructed in liquid paraffin. In addition, TPC2 n are shown to form microporous films up to 15 μm in diameter by simply casting the solutions of some solvents followed by drying for several minutes in air at room temperature. Photoirradiation of the films in the LC temperature range converts them to polymeric ones while preserving the microporous and hexagonally ordered structure. From comparison with TPC1 n and the hydrogenated derivative of TPC2 12, the porous film‐forming property is suggested to result from the combination of the double bond of the cinnamoyl group and the two long alkoxy chains on the phenyl ring. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 605–612

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Section: Resultsmentioning

confidence: 99%

Section: Inrtroductionmentioning

confidence: 99%

Polymeric fibers and microporous films by photo‐crosslinking of triphenylene‐derived liquid crystals

Hirose

Kikuchi

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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“…As has been well documented in crystals, organic molecules tend to pack tightly to fill spaces; therefore, we envisaged that 1 would align linearly to achieve efficient π–π stacking between disciform pyrene-containing π systems (forms A – C in Scheme ). , Although forms A–C might be discriminative stable/metastable states of 1 , if free rotation of the bulky trimethylsilyl groups enabled smooth slippage of the pyrene cores, interconversion of 1 among A–C would be triggered easily by physical stimuli, leading to a change in the fluorescent color and intensity. , …”

Section: Introductionmentioning

confidence: 99%

Trimethylsilyl Group Assisted Stimuli Response: Self-Assembly of 1,3,6,8-Tetrakis((trimethysilyl)ethynyl)pyrene

Nishida¹,

Shinohara²,

Peng³

et al. 2017

Organometallics

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Substitution of 1,3,6,8-tetraethynylpyrene with sterically bulky trimethylsilyl groups enabled four modes of molecular packing, two polymorphs (triclinic system (Y-form) and "loose" crystal Col ho (O K -form)), a "rigid" liquid crystalline phase Col ho (O C -form), and an amorphous phase (O A -form), which emitted fluorescence at different wavelengths under UV light. The four phases could be interconverted by physical stimuli such as heating, grinding by mortar and pestle, and exposing to the vapor of organic solvents.

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“…A terminal azide group was then installed via S N 2 chemistry by treating bromo‐ethyl‐N‐annulated perylene diimide (Br‐C2‐NPDI) with NaN 3. [19] With the azido‐ethyl‐N‐annulated perylene diimide (N 3 ‐C 2 ‐NPDI) precursor, “click” chemistry was employed with tetra(ethynyl)spirobifluorene [47] and tetra(ethynyl)pyrene [48] to afford the target tetramers sbfNPDI 4 and pyrNPDI 4 , respectively (Scheme 2). We note that the yield of sbfNPDI 4 (92 %) was significantly better than that of pyrNPDI 4 (43 %), where the discrepancy in overall yield may be attributed to differences in the rotational freedom of NPDI around the spacer cores which could impact ethynyl accessibility during CuAAC (see Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…Starting material 1,3,6,8-tetraethynylpyrene [pyr(ace) 4 ] was synthesized according to known literature procedure. [48] Pyr(ace) 4 (10.3 mg, 0.0345 mmol, 1 equiv.) and N 3 -C2-NPDI (160 mg, 0.204 mmol, 1 equiv.)…”

Section: Synthesis Of Pyrene[tetrakis(triazole-ethyl-n-annulated Pery...mentioning

confidence: 99%

Development of Tetrameric N‐Annulated Perylene Diimides Using “Click” Chemistry

2022

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Herein, we report the design, synthesis, and characterization of two novel N-annulated perylene diimide (NPDI) tetramer arrays that were developed using copper catalyzed alkyne-azide cycloaddition. Despite the optoelectronic properties of both tetramers being nearly identical, the two tetramers exhibited very different molecular geometries. The twisted spirobifluorene NPDI tetramer (sbfNPDI 4 ) was found to have an extended and flexible geometry, while the planar pyrene NPDI tetramer (pyrNPDI 4 ) exhibited a highly congested and conformationally locked geometry. Organic photovoltaic devices were constructed to demonstrate the use of both new compounds as electron acceptor materials, where slightly higher power conversion efficiencies were achieved with pyrNPDI 4 than sbfNPDI 4 . This study highlights the viability of using "click" chemistry as a facile synthetic strategy towards the development of new multicomponent perylene diimide materials for organic electronic applications.

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Synthesis and Hole Transport Properties of Highly Soluble Pyrene-Based Discotic Liquid Crystals with Trialkylsilylethynyl Groups

Cited by 10 publications

References 28 publications

Polymeric fibers and microporous films by photo‐crosslinking of triphenylene‐derived liquid crystals

Polymeric fibers and microporous films by photo‐crosslinking of triphenylene‐derived liquid crystals

Trimethylsilyl Group Assisted Stimuli Response: Self-Assembly of 1,3,6,8-Tetrakis((trimethysilyl)ethynyl)pyrene

Development of Tetrameric N‐Annulated Perylene Diimides Using “Click” Chemistry

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