Rylene Ribbons with Unusual Diradical Character

Zeng, Wangdong; Phan, Hoa; Herng, Tun Seng; Gopalakrishna, Tullimilli Y.; Aratani, Naoki; Zeng, Zebing; Yamada, Hiroko; Ding, Jun; Wu, Jishan

doi:10.1016/j.chempr.2016.12.001

Cited by 127 publications

(114 citation statements)

References 60 publications

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“…[150] The cyclopenta ring-fused building block was used to construct oligorylenes from the mono-perylene CP-Per to the dodecarylene CP-Dor (Figure 11a), and their optical properties were compared. Wu and co-workers recently synthesized a series of oligomers of one of these materials, 5-AGNRs, also chemically known as polyrylene.…”

Section: Wwwadvancedsciencenewscommentioning

confidence: 99%

“…[155] Wu et al characterized the mixture of N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB) and MoO 3 deposited by coevaporation, creating a CT complex and a new absorption peak appeared at 1350 nm that were not present in either pure NPB or MoO 3 thin film. [150] Copyright 2017, Elsevier Inc. proved experimentally that the orbital hybridization between donor and acceptor molecules plays a critical role in determining the band structure of CT complexes. Energy Mater.…”

Section: Organic Charge Transfer Complexesmentioning

confidence: 99%

See 1 more Smart Citation

Organic Field‐Effect Transistor for Energy‐Related Applications: Low‐Power‐Consumption Devices, Near‐Infrared Phototransistors, and Organic Thermoelectric Devices

Ren

Yang

Gao

et al. 2018

Advanced Energy Materials

112

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The operating frequency of ring oscillators or radio-frequency identification tags made by OFETs have surpassed MHz. [27,28] With the growing level of integration and the operating frequency of OFETs, the power dissipation issue can no longer be ignored. Considering the material composition of most organic semiconductors, controlling the temperature rise within a reasonable range is important to avoid the unwanted degradation of organic materials and therefore maintain stable device operation. In addition, OFETs fabricated on flexi ble substrates somehow limit the use of conventional batteries. To avoid externally wiring the batteries, flexible OFET-based circuits can be expected to be self-powered by integrating them with organic solar cells, thermoelectric modules, or triboelectric nanogenerators. [29,30] All of these demands require OFETs operating with extremely low power consumption. Rapid progress has been made in this field, and research efforts have focused on reducing the operating voltage of OFETs, [31][32][33] enhancing the switching efficiency of transistors, [34][35][36][37] and demonstrating several novel device concepts for low-power applications. [38][39][40][41][42] Despite the switching function, OFETs can also be utilized in emerging energy-related applications, such as near-infrared (NIR) photodetectors and organic thermoelectric devices dueThe organic field-effect transistor (OFET) is the basic building block of integrated circuits. The charge carrier mobility and operating frequency of OFETs have continued to increase; therefore, the power dissipation of OFETs can no longer be ignored. Many research efforts have been made to develop low-power-consumption OFETs and complementary circuits. Despite the switching function, OFETs can also be utilized in emerging energy-related applications, such as near-infrared (NIR) photodetectors and organic thermoelectric devices. Organic phototransistors show considerably higher photo responsivity than other photodetector architectures due to field-effect charge modulation. The photoinduced gate modulating largely suppresses the dark current while simultaneously providing gain. These characteristics may favor NIR light detection and suggest that the organic phototransistor is a promising candidate for optoelectronic applications in the NIR regime. For organic thermoelectric applications, OFETs can work as a powerful tool for examining the charge and energy transport in the organic semiconductor, thus giving insight into organic thermoelectric studies. In this review, the authors highlight recent advances in OFET-related energy topics, including lowpower-consumption OFETs, NIR photodetectors, and organic thermoelectric devices. The remaining challenges in the field will also be discussed.

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Section: Wwwadvancedsciencenewscommentioning

confidence: 99%

Section: Organic Charge Transfer Complexesmentioning

confidence: 99%

Organic Field‐Effect Transistor for Energy‐Related Applications: Low‐Power‐Consumption Devices, Near‐Infrared Phototransistors, and Organic Thermoelectric Devices

Ren

Yang

Gao

et al. 2018

Advanced Energy Materials

112

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“…Particularly, rylenes, namely oligo( peri ‐naphthalene)s, that can be regarded as substructures of graphene nanoribbons (GNR), are currently of great interest for their potential use in a wide range of optoelectronic applications . The bottom‐up covalent synthesis in solution is one of the most exploited strategies for the preparation of well‐defined low band gap GNRs with tunable opto‐electronic properties . Up to now, higher order rylenes such as terrylene, quaterrylene, pentarylene and hexarylene and their dicarboxylic imide derivatives have been synthesized.…”

Section: Introductionmentioning

confidence: 99%

“…[ ][ ] However, to the best of our knowledge, up to the present only a few reports describe the bay‐substitution of higher order rylenes that do not bear imide functionalities on the peri position. [ ][ ][ ] After the first synthesis of an unsubstituted quaterrylene reported by Clar in 1948, the preparation of the first soluble alkyl‐functionalized quaterrylene derivative through alkali‐metal induced cyclization of oligonaphthalene precursors was reported by Müllen and co‐workers in 1990 . Important intermediates bearing four solubilizing tert ‐octylphenoxy groups in the bay positions of the perylene core have been reported by the same author in a pivotal work concerning the synthesis of soluble polymer with a poly( peri ‐naphthalene) (PPN) backbone .…”

Section: Introductionmentioning

confidence: 99%

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Miletić

Fermi

Papadakis

et al. 2017

Helvetica Chimica Acta

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The preparation of the first soluble quaterrylene derivative featuring peripheral tert‐butyl substituents and sterically hindering, core‐anchored triflate groups has been achieved. This involves a facile synthetic route based on an oxidative coupling of perylene precursors in the presence of H2O2 as oxidant. The steric hindrance between the TfO substituents at the central bay position of the quaterrylene board triggers a strong deformation of the central perylene planarity, which forces the quaterrylene platform to adopt a twisted geometry as shown by X‐ray analysis. Exceptionally, photophysical investigations show that the core‐twisted quaterrylene phosphoresces in the NIR spectral region at 1716 nm. Moreover, third‐order nonlinear optical measurements on solutions and thin film containing the relevant molecule showed very large second hyperpolarizability values, as predicted by theoretical calculations at the CAM‐B3LYP/6‐31G** level of theory, making this material very appealing for photonic applications.

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“…68 Though the oligorylenes behave as connected naphthalenes (Figure 17a), it is predicted that the longer rylenes exhibit diradical character even in the neutral state. 69 Furthermore, early theoretical calculations have indicated the neutral polyrylene as either parallel polyacetylene chains (Figure 17b), or a planar poly( p-phenylene) bridged by double bonds (Figure 17c).…”

mentioning

confidence: 99%

Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue

Matsumoto

Suzuki

Hayashi

et al. 2017

Bulletin of the Chemical Society of Japan

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she was a researcher of PRESTO, JST, and then a group leader of CREST project (2010)(2011)(2012)(2013)(2014)(2015)(2016), JST, on "Construction of organic thin-film solar cells with innovative solutionprocessible organic materials". Her current research focuses on the development of functional organic materials including solution-processable molecular materials for organic electronics applications, large acenes and bottom-up synthesis of graphene nanoribbons. AbstractThe structure and electronic features of neutral and positively charged pyrene and perylene derivatives were explored. The radical cation of 1,3,6,8-tetraarylpyrene 1 was examined by ESR, UVvisNIR spectroscopy and theoretical calculations. The addition of 2 equiv of oxidant to 1 resulted in the formation of dication 1 2+. The single-crystal X-ray structure of 1 2+ proved that the aromatic part relocates from biphenyl unit to naphthyl unit upon 2e ¹ oxidation of 1. We have also investigated the oxidation processes of 3,9-diarylperylene 2 and 3,10-diarylperylene 3. The radical cations of 2•+ and 3 •+ showed ESR signals and the spin densities were proven to delocalize at 3,4,9,10-positions. In the case of doubly charged 3,9-diarylperylene, we could find the anthracene structure in the core, while the phenanthrene skeleton appeared in two-electron oxidized 3,10-diarylperylene. Finally we validated this phenomenon to apply for the higher analogue terrylene, discovering its large aromaticity relocation upon the 2e ¹ oxidation.

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Rylene Ribbons with Unusual Diradical Character

Cited by 127 publications

References 60 publications

Organic Field‐Effect Transistor for Energy‐Related Applications: Low‐Power‐Consumption Devices, Near‐Infrared Phototransistors, and Organic Thermoelectric Devices

Organic Field‐Effect Transistor for Energy‐Related Applications: Low‐Power‐Consumption Devices, Near‐Infrared Phototransistors, and Organic Thermoelectric Devices

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue

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