Tetraphenylethene–triphenylene oligomers with an aggregation-induced emission effect and discotic columnar mesophase

Yu, Wenhao; Chen, Chao; Hu, Ping; Wang, Bi‐Qin; Redshaw, Carl; Zhao, Ke‐Qing

doi:10.1039/c3ra41874j

Cited by 49 publications

(31 citation statements)

References 75 publications

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“…Aggregation-caused quenching (ACQ) accompanied by a red-shift from 447 nm to 471 nm was observed instead of aggregation-induced emission (AIE). [58,59 Gelling Behavior…”

Section: Photophysical Properties: Uv/vis Absorption and Fluorescent mentioning

confidence: 99%

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Wang

Zhao

et al. 2019

ChemPlusChem

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Board‐like liquid‐crystalline semiconductors based on the dithieno[3,2‐b;2′,3′‐d]thiophene (DTT) substructure were synthesized and their thermal, self‐assembly, optical, and semiconducting properties investigated. These sanidic compounds, bearing eight peripheral chains, are mesomorphic and spontaneously self‐assemble into columnar hexagonal mesophases (Colhex) over broad temperature ranges, as confirmed by polarized optical microscopy, differential scanning calorimetry, and small‐angle X‐ray scattering. Strong blue photoluminescence with absolute quantum yields up to 33 % were measured. These compounds also form blue‐light emitting gels in various organic solvents. The fibrillar‐like morphology of these gels, reminiscent of the columnar structure, and stabilized by efficient intermolecular interactions, was characterized by scanning electron microscopy. The charge carrier mobility of these π‐extended mesogens was measured by time‐of‐flight transient photocurrent technique in the Colhex mesophase, and showed good hole‐transport performance with charge carrier mobility of 10−3 cm2 V−1 s−1.

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“…Aggregation-caused quenching (ACQ) accompanied by a red-shift from 447 nm to 471 nm was observed instead of aggregation-induced emission (AIE). [58,59 Gelling Behavior…”

Section: Photophysical Properties: Uv/vis Absorption and Fluorescent mentioning

confidence: 99%

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Wang

Zhao

et al. 2019

ChemPlusChem

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“…For example, Zhao and co-workers reported as eries of tetraphenylethene-triphenylene oligomers, in which the tetraphenylethene was responsible for AIE and the triphenylenes induce mesomorphism. [21] In this case, the mesophase formed only upon adding trinitrofluorenone. This additive was also required for forming ac harge-transfer complex.…”

Section: Introductionmentioning

confidence: 94%

“…The design strategy for previously investigated AIE columnar materials has been to covalently link the two components; one responsible for AIE and the other for columnar mesomorphism. For example, Zhao and co‐workers reported a series of tetraphenylethene–triphenylene oligomers, in which the tetraphenylethene was responsible for AIE and the triphenylenes induce mesomorphism . In this case, the mesophase formed only upon adding trinitrofluorenone.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Liquid‐Crystalline Tetraoxapentacene Derivatives Exhibiting Aggregation‐Induced Emission

Hiscock

Raycraft

Wałęsa‐Chorab

et al. 2018

Chemistry A European J

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A series of new tetrakis(dialkoxyphenyl) dicyanotetraoxapentacene derivatives (1 a–c) were prepared by reaction of the appropriate terphenyl diols with tetrafluoroterephthalonitrile in good yields. Compounds 1 b and 1 c, which bear hexyloxy and decyloxy side chains, exhibited columnar hexagonal mesophases, as shown by polarized optical microscopy, variable‐temperature powder X‐ray diffraction, and differential scanning calorimetry. Single‐crystal X‐ray diffraction of methoxy‐substituted 1 a revealed that the dicyanotetraoxapentacene core is highly planar, consistent with the notion that these molecules are able to stack in columnar mesophases. A detailed photophysical characterization showed that these compounds exhibit aggregation‐induced emission in solution, emission in nonpolar solvents, weak emission in polar solvents, and strong emission in the solid state both as powder and in thin films. These observations are consistent with a weakly emissive charge‐transfer state in polar solvents and a more highly emissive locally excited state in nonpolar solvents.

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“…Yu et al also obtainedp ure Z/E stereoisomers by using the click reaction. [53] As shown in Scheme 3a,e thynyl groupsw ere linked to aT PE core througha lkoxy linkers, and then triphenylene oligomers were introduced in an alkyne-azide cycloaddition reaction. The large configurational difference between (Z)-TPEATand (E)-TPEATenabled their separation by using column chromatography.T he meltingp oints of the first ands econd eluted compounds were 150 and 92 8C, respectively.B ecause E isomerst ypically show higher molecular symmetry and lower polarity,t he first eluted compound was designateda s( E)-TPEAT.…”

Section: Development Of Z/e Isomers Of Tpe Derivativesmentioning

confidence: 99%

Recent Advances in the Z/E Isomers of Tetraphenylethene Derivatives: Stereoselective Synthesis, AIE Mechanism, Photophysical Properties, and Application as Chemical Probes

Xie

2019

Chemistry An Asian Journal

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Focused research on the Z/E isomerso ft etraphenylethene (TPE) derivatives is scarce in comparison with the thousands of luminogens with AIE properties (AIEgens) that have been synthesized based on the TPE moiety.T he similar chemical and physical properties of the Z/E isomersm ake them difficult to separate by using conventional chromatographic techniques.H owever,t hey can be isolated by introducing polar groupsa nd the pure isomers exhibit very different photophysical properties, mechanochromism, and host-guestc oordination,a sw ell as assisting in deciphering the AIE mechanism. In this Minireview, we present an overview of the disagreement regarding the AIE mechanism between the restriction of intramolecular vibration and photoinduced Z/E isomerization. Then, we discuss the development of (Z)-/(E)-TPE derivatives, their use in host-guest detection, and their mechanoluminescence properties, with a focus on their photophysical characteristics. Finally,w ee xplore the stereoselective synthesis of pure (Z)-/(E)-TPE derivatives.

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Tetraphenylethene–triphenylene oligomers with an aggregation-induced emission effect and discotic columnar mesophase

Cited by 49 publications

References 75 publications

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Synthesis and Characterization of Liquid‐Crystalline Tetraoxapentacene Derivatives Exhibiting Aggregation‐Induced Emission

Recent Advances in the Z/E Isomers of Tetraphenylethene Derivatives: Stereoselective Synthesis, AIE Mechanism, Photophysical Properties, and Application as Chemical Probes

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