Anthracene derivative based multifunctional liquid crystal materials for optoelectronic devices

Wang, Yunrui; Fang, Daqi; Fu, Tianchen; Ali, Muhammad Umair; Shi, Yuhao; He, Yaowu; Zhao, Haiyan; Yan, Chaoyi; Mei, Zongwei; Meng, Hong

doi:10.1039/d0qm00038h

Cited by 27 publications

(19 citation statements)

References 48 publications

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“…Anthracene derivatives have been widely studied as materials for organic electronics and other applications and continue to be of immense interest in various fields of materials chemistry and beyond. [1][2][3][4][5][6][7][8][9] New synthetic methods keep being developed to facilitate the preparation of known anthracene derivatives and to enable the preparation and study of new derivatives, e.g. our recently developed method for the synthesis of substituted 9,10-anthracenedicarbonitriles (also known as 9,10dicyanoanthracenes).…”

Section: Introductionmentioning

confidence: 99%

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Meindl¹,

Pfennigbauer²,

Stöger³

et al. 2020

Preprint

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Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

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Section: Introductionmentioning

confidence: 99%

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Meindl¹,

Pfennigbauer²,

Stöger³

et al. 2020

Preprint

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“…The pure product was obtained as a white solid (yield: 27%). 1 51 After column chromatography (PE/EA, 15/1, V/V), the product was furnished as a cloudy, waxy, and yellowish solid at RT in 61% yield. 1 H NMR (400 MHz, CD 2 Cl 2 ): δ 6.95 (d, J = 8.7 Hz, 8H), 6.73 (d, J = 8.8 Hz, 8H), 6.60 (s, 8H), 4.86 (s, 8H), 3.93 (dt, J = 17.9, 6.6 Hz, 24H), 1.79−1.68 (m, 24H), 1.53−1.30 (m, 72H), 0.90 (m, 36H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Peripherally Modified Tetraphenylethene: Emerging as a Room-Temperature Luminescent Disc-Like Nematic Liquid Crystal

Wang

Cao

et al. 2021

ACS Appl. Mater. Interfaces

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A blue-light-emitting liquid crystalline (LC) material was designed and prepared. By employing a twisted luminescent core (i.e., tetraphenylethene), four peripheral LC units with long alkyl chains and the small polar benzyl-ether-typed linking groups, the resulting material displayed a hexagonal columnar phase near room temperature and a disc-like nematic phase between 32 and 70 °C. The columnar LC showed a high quantum yield of 0.49 at 20 °C, and the efficient luminescence property was retained even in the isotropic phase at high temperature. Additionally, the fluidity of the nematic phase rendered the LC a non-volatile solvent, and the proper addition of a red dye led to the achievement of polarized white-light emission, which revealed a promising application prospect in LC display fabrication.

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“…Regarding the applications of anthracenes, tunable luminescence and easy charge transfer coupled with the unique ability of the reversible dimerization make anthracenes valuable building blocks for the generation of light responsive materials [9,29,30]. This includes various polymeric materials [30,31], such as intelligent shape memory polymers [32], as well as soft materials, such as photoresponsive hydrogels [16] and liquid crystals [33]. Hence, the main applications cover a vast number of fields, including tissue engineering [30], optoelectronic devices [33] such as organic light-emitting diodes or transistors [34], sensors for metal ion detection [35], molecular containers for catalysis or drug delivery [36] and photomedicine, where these compounds can be used as intracellular pH probes [37], DNA-based hybridization sensors [38] and other biosensors [39].…”

Section: Introductionmentioning

confidence: 99%

“…This includes various polymeric materials [30,31], such as intelligent shape memory polymers [32], as well as soft materials, such as photoresponsive hydrogels [16] and liquid crystals [33]. Hence, the main applications cover a vast number of fields, including tissue engineering [30], optoelectronic devices [33] such as organic light-emitting diodes or transistors [34], sensors for metal ion detection [35], molecular containers for catalysis or drug delivery [36] and photomedicine, where these compounds can be used as intracellular pH probes [37], DNA-based hybridization sensors [38] and other biosensors [39]. According to the latest results, anthracene derivatives have even been suggested as potential candidates for applications in laser photonics [40] and as smart optical materials [41].…”

Section: Introductionmentioning

confidence: 99%

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

et al. 2021

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Anthracenes are an important class of acenes. They are being utilized more and more often in chemistry and materials sciences, due to their unique rigid molecular structure and photoreactivity. In particular, photodimerization can be harnessed for the fabrication of novel photoresponsive materials. Photodimerization between the same anthracenes have been investigated and utilized in various fields, while reactions between varying anthracenes have barely been investigated. Here, Nuclear Magnetic Resonance (NMR) spectroscopy is employed for the investigation of the photodimerization of two exemplary anthracenes: anthracene (A) and 9-bromoanthracene (B), in the solutions with only A or B, and in the mixture of A and B. Estimated k values, derived from the presented kinetic model, showed that the dimerization of A was 10 times faster in comparison with B when compounds were investigated in separate samples, and 2 times faster when compounds were prepared in the mixture. Notably, the photoreaction in the mixture, apart from AA and BB, additionally yielded a large amount of the AB mixdimer. Another important advantage of investigating a mixture with different anthracenes is the ability to estimate the relative reactivity for all the reactions under the same experimental conditions. This results in a better understanding of the photodimerization processes. Thus, the rational photofabrication of mix-anthracene-based materials can be facilitated, which is of crucial importance in the field of polymer and material sciences.

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Anthracene derivative based multifunctional liquid crystal materials for optoelectronic devices

Abstract: A liquid crystal molecule with versatile properties, like the indicators of a clock, shows various applications.

Cited by 27 publications

References 48 publications

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Peripherally Modified Tetraphenylethene: Emerging as a Room-Temperature Luminescent Disc-Like Nematic Liquid Crystal

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

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