Synthesis and investigation on optoelectronic properties of mesogenic triphenylene–perylene dyads linked by ethynylphenyl bridges

Kong, Xiangfei; Gong, Hongkang; Liu, Peng; Yao, Wei; Liu, Zheng; Wang, Guixia; Zhang, Shufen; He, Zhengjie

doi:10.1039/c7nj04328g

Cited by 11 publications

(16 citation statements)

References 52 publications

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“…In fact, bringing the discotic PBI-based LCs more closely to practical applications requires excellent mesomorphic and emission properties. Up to now, although a plenty of discotic PBI-based LCs were achieved using various mesomorphic groups such as triphenylene [26][27][28][29][30], cholesterol [31,32], siloxane [33], dendritic peptides [34], cyclotetrasiloxane [35], oligosiloxane [36], polyhedral oligosilsesquioxane (POSS) [37], and gallic acid derivatives [38][39][40][41][42], most of their uorescence emission were regulated and managed by substituted groups through the intramolecular charge-transfer (ICT) and/or π-extended conjugation system. While hardly affecting the alteration of emission peak, the substituents at the N-imide positions can weaken the uorescence because of the photoinduced electron transfer (PET) [22], which limit the practical application of the uorescent PBI-based LCs in photoelectronic and electroluminescent devices.…”

Section: Introductionmentioning

confidence: 99%

Fluorescein-bridged Perylene Bisimide Dimer for Use as Liquid Crystal: Studies on Mesomorphic and Fluorescence Properties

et al. 2021

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A novel uorescein-bridged perylene bisimide (PBI) dimer for liquid crystal (LC) with geometrically symmetric structure was developed. The mesomorphic results indicated that the energetically stable and unstable conformers of uorescein fragments could lead to the transformation of mesophases from a hexagonal columnar mesophase to an uncertain phase at 136.9 °C in heating, whilst a stable hexagonal columnar mesophase maintained between 175.6 °C and 58.6 °C in cooling. The selectively excited uorescence characters in THF solution demonstrated that the uorescence resonance energy transfer (FRET) effect between uorescein fragments and PBI unites could provide a means to effectively impose strong uorescence of the dimeric PBIs modi ed with suitable chromophore at the N-imide position, which alternatively serves as a platform for the further study of multi-functional PBI-based LCs.

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Section: Introductionmentioning

confidence: 99%

Fluorescein-bridged Perylene Bisimide Dimer for Use as Liquid Crystal: Studies on Mesomorphic and Fluorescence Properties

et al. 2021

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“…Several groups have worked on dyads and triads of PBIs N-substituted with one or two alkyloxytriphenylenes for the construction of segregated columns of acceptor PBI and donor triphenylene units (Figure 15). [110,[117][118][119] Two examples are dyad PBI-71 and triad PBI-72 of which the triad indeed self-organizes into separate columns of PBI acceptor and triphenylene donor molecules in an oblique columnar lattice. The dyad arranges into a hexagonal columnar mesophase with each column containing stacks of both donor and acceptor molecules.…”

Section: Pbi-23mentioning

confidence: 99%

Columnar Mesomorphism of Board‐Shaped Perylene, Diketopyrrolopyrrole, Isoindigo, Indigo, and Quinoxalino‐Phenanthrophenazine Dyes

et al. 2021

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The properties of organic dyes depend as much on their intermolecular interactions as on their molecular structure. While it is generally predictable what supramolecular structure would be ideal for a specific application, the generation of specific supramolecular structures by molecular design and suitable processing methods remains to be a challenge. A versatile approach to different supramolecular structures has been the application of mesomorphism in conjunction with alignment techniques and self‐assembly at interfaces. Reviewed here is the columnar mesomorphism of board‐shaped dyes perylene, indigo, isoindigo, diketopyrrolopyrrole, and quinoxalinophenanthrophenazine. They generate a larger number of different supramolecular structures than conventional disc‐shaped (discotic) mesogens because of their non‐circular shape and directional intermolecular interactions. The mesomorphism of all but the perylene derivatives is systematically and comprehensively covered for the first time.

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“…reported the donor‐acceptor dyads having triphenylene (donor)‐ perylene monoimide dihexyl ester (acceptor) connected through ethynylphenyl bridges which exhibit broad Col h phase. These extended π–conjugation in aforementioned compound results an intramolecular photo‐induced electronic charge transfer between the donor and acceptor units . Recently, electron rich character of triphenylene twin linking through electron deficient nature of pyrazine ring that represents a donor‐acceptor‐donor framework like extended π−conjugation with wide range mesomorphic properties is reported by Cammidge et al …”

Section: Introductionmentioning

confidence: 96%

Charge Transport in Novel Phenazine Fused Triphenylene Supramolecular Systems

et al. 2018

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Novel phenazine-fused triphenylene discotic liquid crystals (DLCs) tethered with alkanethiols and alkoxy chains are synthesized. The condensation of 4,5-dibromobenzene-1,2diamine with triphenylene-1,2-diquinone discotic core, followed by the reaction with alkanethiols gives heterocyclic phenazinefused triphenylene based DLCs. The intermediate dibromosubstituted phenazine and final alkanethiol substituted phenazine-fused triphenylene derivatives exhibit a wide range of stable enantiotropic hexagonal columnar phase, which was characterised by polarized optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD) studies. We have also investigated the photophysical properties of all phenazine compounds using dilute solution of anhydrous chloroform. The charge carrier mobility was measured for one representative compound by time of flight method which revealed that phenazine-fused triphenylene discotic mesogen exhibits p-type (hole) mobility of the order of 10 À4 cm 2 V À1 s À1 . The novel mesogens reported here present a wide temperature stability with good charge mobility and optical properties. These mesogens have shown potential applications for solar cells, sensors, organic light emitting diodes and other electrooptical device applications.[a] A.

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Synthesis and investigation on optoelectronic properties of mesogenic triphenylene–perylene dyads linked by ethynylphenyl bridges

Abstract: Columnar mesogenic dyads consisting of triphenylene and perylene units are a novel kind of single-component photovoltaic materials.

Cited by 11 publications

References 52 publications

Fluorescein-bridged Perylene Bisimide Dimer for Use as Liquid Crystal: Studies on Mesomorphic and Fluorescence Properties

Fluorescein-bridged Perylene Bisimide Dimer for Use as Liquid Crystal: Studies on Mesomorphic and Fluorescence Properties

Columnar Mesomorphism of Board‐Shaped Perylene, Diketopyrrolopyrrole, Isoindigo, Indigo, and Quinoxalino‐Phenanthrophenazine Dyes

Charge Transport in Novel Phenazine Fused Triphenylene Supramolecular Systems

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