1,8‐Substituted Pyrene Derivatives for High‐Performance Organic Field‐Effect Transistors

Gong, Xue; Zheng, Chaoyue; Feng, Xingcui; Huan, Yihong; Li, Jiewei; Yi, Moonsuk; Fu, Zhenqian; Huang, Wei; Gao, Deqing

doi:10.1002/asia.201801408

Cited by 12 publications

(13 citation statements)

References 48 publications

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“…1,8-Disubstituted pyrenes dedicated for materials that can be used as high-performance organic field-effect transistors containing 5-octyl-2-thienyl 57 and 5-octyl-(2,2′-bithiophen)-5′-yl 58 substituents were obtained with 73% and 40% yields, as described by Deqing Gao et al (Scheme 36) [11].…”

Section: Dibromopyrenesmentioning

confidence: 99%

“…Synthesis of 1,8-bis(5-octyl-2-thienyl)pyrene 57 and 1,8-bis[5 -octyl-(2,2′-bithiophen)-5′-yl]pyrene 58 [11]. …”

Section: Figure Schemes and Tablesmentioning

confidence: 99%

“…Disubstituted pyrenes of this type are interesting in themselves and can act as substrates in the synthesis of the other molecules that also exhibit expected properties. The vast majority of disubstituted pyrenes can be applied in organic electronics in materials such as organic light-emitting diodes (OLEDs) [4,5,6,7,8,9], organic field-effect transistors (OFETs) [10,11], and solar cells [12] but also in the synthesis of nanographenes [13], metal cages [14,15], and many others. A wide spectrum of methods for the synthesis of the reported compounds exists, though a fundamental problem lies within the methods’ ordering.…”

Section: Introductionmentioning

confidence: 99%

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Non-K Region Disubstituted Pyrenes (1,3-, 1,6- and 1,8-) by (Hetero)Aryl Groups—Review

Zych

2019

Molecules

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Disubstituted pyrenes at the non-K region by the same or different (hetero)aryl groups have proven to be an increasingly interesting area of research for scientists over the last decade due to their optical and photophysical properties. However, in this area, there is no systematization of the structures and synthesis methods nor their limitations. In this review, all approaches to the synthesis of these compounds, starting from the commercially available pyrene are described. Herein, the ways of obtaining of disubstituted intermediates based on bromination and acylation reaction are presented. This is crucial in the determination of the possibility of further functionalization by using coupling, cycloaddition, condensation, etc. reactions. Moreover, the application of disubstituted pyrenes in the synthesis of 1,3,6,8-tetrasubstituted was also reviewed. This review describes the directions of research on chemistry of disubstituted pyrenes.

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Section: Dibromopyrenesmentioning

confidence: 99%

“…Synthesis of 1,8-bis(5-octyl-2-thienyl)pyrene 57 and 1,8-bis[5 -octyl-(2,2′-bithiophen)-5′-yl]pyrene 58 [11]. …”

Section: Figure Schemes and Tablesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Non-K Region Disubstituted Pyrenes (1,3-, 1,6- and 1,8-) by (Hetero)Aryl Groups—Review

Zych

2019

Molecules

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“…One of the most important driving forces enabling the use of pyrene over a wide range of applications is the possible functionalization of its molecular backbone [1] . Accordingly, previous research in the field has focused on modifying the properties of pyrene by introducing substituents at the periphery of the molecule [2–3,5] or by incorporating pyrene units into semiconducting polymers [4,6] . In contrast, the influence of the topology of the π‐electron system on the properties of pyrene has not yet been addressed.…”

Section: Introductionmentioning

confidence: 99%

Topology Effects in Molecular Organic Electronic Materials: Pyrene and Azupyrene**

et al. 2021

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Pyrene derivatives play a prominent role in organic electronic devices, including field effect transistors, light emitting diodes, and solar cells. The flexibility in the desired properties has previously been achieved by variation of substituents at the periphery of the pyrene backbone. In contrast, the influence of the topology of the central -electron system on the relevant properties such as the band gap or the fluorescence behavior has not yet been addressed. In this work, pyrene is compared with its structural isomer azupyrene, which has a -electron system with nonalternant topology. Using photoelectron spectroscopy, near edge X-ray absorption fine structure spectroscopy, and other methods, it is shown that the electronic band gap of azupyrene is by 0.72 eV smaller than that of pyrene. The difference of the optical band gaps is even larger with 1.09 eV, as determined by ultraviolet-visible absorption spectroscopy. The nonalternant nature of azupyrene is also associated with a more localized charge distribution, as can be seen in 1 H and 13 C nuclear magnetic resonance shifts, as well as the C1s core-level shifts. Further insight is provided by density functional theory (DFT) calculations of the molecular properties and ab initio coupled cluster calculations of the optical transitions. The concept of aromaticity is used to interpret DFT-based structures and for the theoretical assignment of the vibrational modes of the infrared spectra, where major topology-related differences are apparent.

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“…[4] One of the most important driving forces enabling the use of pyrene over a wide range of applications is the possible functionalization of its molecular backbone. [1] Accordingly, previous research in the field has focused on modifying the properties of pyrene by introducing substituents at the periphery of the molecule [2][3]5] or by incorporating pyrene units into semiconducting polymers. [4,6] In contrast, the influence of the topology of the -electron system on the properties of pyrene has not yet been addressed.…”

Section: Introductionmentioning

confidence: 99%

Topology Effects in Molecular Organic Electronic Materials: Pyrene and Azupyrene

Klein¹,

Ruppenthal²,

Hall³

et al. 2021

Preprint

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Pyrene derivatives play a prominent role in organic electronic devices, including field effect transistors, light emitting diodes, and solar cells. The flexibility in the desired properties has previously been achieved by variation of substituents at the periphery of the pyrene backbone. In contrast, the influence of the topology of the central pi-electron system on the relevant properties such as the band gap or the fluorescence behavior has not yet been addressed. In this work, pyrene is compared with its structural isomer azupyrene, which has a pi-electron system with nonalternant topology. Using photoelectron spectroscopy, near edge X-ray absorption fine structure spectroscopy, and other methods, it is shown that the electronic band gap of azupyrene is by 0.72 eV smaller than that of pyrene. The difference of the optical band gaps is even larger with 1.09 eV, as determined by ultraviolet–visible absorption spectroscopy. The nonalternant nature of azupyrene is also associated with a more localized charge distribution, as can be seen in 1H and 13C nuclear magnetic resonance shifts, as well as the C1s core-level shifts. Further insight is provided by density functional theory (DFT) calculations of the molecular properties and ab initio coupled cluster calculations of the optical transitions. The concept of aromaticity is used to interpret DFT-based structures and for the theoretical assignment of the vibrational modes of the infrared spectra, where major topology-related differences are apparent.

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1,8‐Substituted Pyrene Derivatives for High‐Performance Organic Field‐Effect Transistors

Cited by 12 publications

References 48 publications

Non-K Region Disubstituted Pyrenes (1,3-, 1,6- and 1,8-) by (Hetero)Aryl Groups—Review

Non-K Region Disubstituted Pyrenes (1,3-, 1,6- and 1,8-) by (Hetero)Aryl Groups—Review

Topology Effects in Molecular Organic Electronic Materials: Pyrene and Azupyrene**

Topology Effects in Molecular Organic Electronic Materials: Pyrene and Azupyrene

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