Organic electron transport materials

• Joseph Cameron and
• Peter J. Skabara

Beilstein J. Org. Chem. 2024, 20, 672–674, doi:10.3762/bjoc.20.60

• transport materials for organic semiconductor devices due to their potential to be applied in various technologies. For example, such materials can be used to improve charge balance in the emissive layer of an organic light-emitting diode, charge extraction in perovskite solar cells or used as the

• semiconductor layer of n-type organic field-effect transistors. Typically, an electron transport material should have a high electron mobility and a low-lying lowest unoccupied molecular orbital (LUMO) relative to vacuum. This is achieved by using electron-deficient units containing highly electronegative

• and allow for the construction of efficient, solution-processed devices. It is exciting to see how much of the work establishing n-type organic semiconductor materials for OFETs, for example, is now being applied to emerging technologies such as organic electrochemical transistors. In this case

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• , Yamada, Fukui, Shinokubo and co-workers tackled the synthesis of perylene bisimide (PBI), a valuable n-type semiconductor, via a “precursor approach” based on the late-stage extrusion of S-based fragments [57]. Dinaphthothiepine bisimides 3a and 3b, bearing octyl- and butylimide substituents respectively

• lower temperature (140 °C) than previously. These preliminary studies thus validated the suitability of the dinaphthothiepine core and particularly its S-oxide as soluble precursors for perylene, with three different activation modes to generate the target PBI semiconductor. This “precursor approach

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• derivatives are among the most investigated due to their easy functionalization, high chemical and thermal stability, strong photoluminescence, and n-type semiconductor character. They tend to adopt columnar organization due to the strong π–π interaction of the rigid cores, providing a path for the efficient

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• processability compared to their inorganic counterparts [1][2]. Charge transport in organic semiconductors is a fundamental aspect that governs the performance and functionality of various organic semiconductor devices, such as organic solar cells (OSCs), organic field-effect transistors (OFETs), organic light

• chromophores in the development of organic light-emitting diodes (OLEDs), sensors, and electrochromic devices [8][13][14]. In this review, we have comprehensively examined the recent advancements of Qx-derived ETMs in various applications within the organic semiconductor device field over the past five to six

• materials, offering a range of properties specifically tailored for OFET applications. The tunable properties of Qxs as n-type semiconductor materials, including high electron mobility, optimal energy levels, broad absorption spectra, and processing compatibility, position them as promising candidates for

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• proper energy levels will benefit the efficient charge injections from the electrodes in OLEDs. To evaluate charge-carrier mobility in TPECNz, hole (μh) and electron (μe) mobilities were initially measured using metal-insulator-semiconductor (MIS) diodes in combination with charge extraction in linearly

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• strength and their reactivity with organic semiconductors (SC) does not depend solely on the SC reduction potential, since the first step, at least in many cases, is a hydride transfer rather than an electron transfer [8][9]. Moreover, as well forming the desired semiconductor radical anion SC•−, and the

• stable DMBI+ (1+) species, a hydrogen atom must be lost from the dopant, in some cases resulting in the incorporation of hydrogen-reduced side products into the semiconductor film [9], although in other cases it may be lost as H2 [8][10][11]. The first report of a (DMBI)2 dimer (12, Figure 1) was of 1a2

• , whereby the dimer is in equilibrium with a small concentration of the corresponding odd-electron monomer, which can then rapidly react with an acceptor such as an organic semiconductor (SC) through an exergonic electron transfer (ET), has been observed for the reactions of several relatively weakly bonded

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• materials. Radical depolymerization, an efficient approach to destroy polymers, finds applications in two distinct fields, semiconductor industry and environmental protection. Polymer chemistry has largely diverged from organic chemistry with the fine division of modern science but polymer chemists

• in the post-polymerization modification. However, it is also an important chemical process in several circumstances. Photoresist is one of the bedrocks of the semiconductor industry [188][189]. There are two types of photoresists, positive and negative photoresists, and they become more or less

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• photocatalysts. Unlike photocatalysis with unrecycled sacrificial donors, the reaction does not depend on the total consumption of the donor. Z-schemes are generally achieved by transfer of electrons to semiconductor particles with photocharged interfaces that can accumulate charge and provide a potential

• photoreduction, with their energy levels arranged so that they operate together to transfer electrons from one substrate to another (Figure 3). Artificial Z-schemes were used for photochemical water splitting before carbon dioxide reduction and are mainly being investigated using particulate semiconductor

• -schemes are usually developed independently with different donors. Recently Ma et al. have developed a carbon dioxide reduction photosystem composed of a cobalt–quaterpyridine catalyst anchored to carbon nitride semiconductor particles [55]. Rather than an inorganic sacrificial donor, they developed this

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

• Damiano Diprima,
• Hannes Gemoets,
• Stefano Bonciolini and
• Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

• electrochemistry, the electron transfer occurs locally at the surface of the physical electrodes (typically located at a distance in the range of 200 μm to 2 cm) on which a potential is induced by an external potentiostat (Scheme 2). While for photoredox chemistry, the light-activated semiconductor catalyst

• . A) Effect of the addition of 1 equiv of various acids and bases to the standard solution. B) Effect of the addition of 1 equiv of various salts to the standard solution. Oxidation of heteroatoms. Graphical representation comparing A electrochemistry and B photoredox catalysis using a semiconductor

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• this [7]helicene family by introducing different linkers such as nitrogen, sulfur, sulfone, ketone, methylene, and derivatives of ketone [44]. Due to the varied nature of the different linkers, the photophysical and semiconductor properties can be effectively tuned. Feng and co-workers reported a

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• unstable, for example, towards oxidation. So, we have chosen tetracene as the object of our research. This molecule is also known as an organic semiconductor and is poorly soluble, but it demonstrates some stability to oxidation, making it easier to work with. We assumed these results might be extended to

Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties

• Shinsuke Inagi and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 1505–1506, doi:10.3762/bjoc.18.158

• of organic electrochemistry for energy material applications. Organic semiconductor design for electron or hole transport is important for transistor and solar cell applications, and redox-active (but stable) organic and polymeric materials are promising for secondary batteries and redox flow

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• University, Cigli, 35620-Izmir, Turkey Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, UK, KY16 9ST Organic Semiconductor Centre, SUPA School of Physics and Astronomy, University of St Andrews, St Andrews KY16 9SS, UK Instituto de Ciencia Molecular (ICMol

• fluorescence; Introduction Light-emitting electrochemical cells (LEECs) are thin film light-emitting devices typically consisting of an emissive layer containing ionic species that facilitate charge transport and an emissive semiconductor material. The emissive layer is sandwiched between two air-stable

Electrochemical formal homocoupling of sec-alcohols

• Kosuke Yamamoto,
• Kazuhisa Arita,
• Masashi Shiota,
• Masami Kuriyama and
• Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

• ][16][17][18]. In addition to the reductive coupling of carbonyl compounds, oxidative homocoupling reactions of benzyl alcohols under transition metal- or semiconductor-based photoredox catalysis have been demonstrated as attractive approaches to access vic-1,2-diols [19][20][21][22][23

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• s−1. Keywords: dithienothiophene (DTT); fused ring system; organic field-effect transistor (OFET); organic semiconductor; thienoacene; Introduction In recent years, organic molecules with several fused aromatic rings have gained much attention. Fusing aromatic rings leads to planar structures

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• -(1-pyrenyl)-4-octylquinoline) (BPYOQ, compound 3 in Figure 5), which could be tuned in the whole visible range through the complex reaction with CSA [35]. This is supposed to be the first EL example of the protonated organic semiconductor. Compound 3 is an aromatic end-capped oligoquinoline, with

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• as high-energy materials [23][24][25], molecules with promising photophysical, electrochemical and coordination properties for use in sensors, OLEDs, semiconductor materials, etc. [26][27][28]. The most important biomedical application of 1,2,4,5-tetrazines are bioorthogonal reactions that allow

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• Ettore Crovini Zhen Zhang Yu Kusakabe Yongxia Ren Yoshimasa Wada Bilal A. Naqvi Prakhar Sahay Tomas Matulaitis Stefan Diesing Ifor D. W. Samuel Wolfgang Brutting Katsuaki Suzuki Hironori Kaji Stefan Brase Eli Zysman-Colman Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of

• Augsburg, Universitätstrasse. 1, 86159 Augsburg, Germany Organic Semiconductor Centre, SUPA, School of Physics and Astronomy, University of St Andrews, North Haugh, St Andrews, KY16 9SS, UK Institute of Biological and Chemical Systems – Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of

• 100% IQE is just the first step toward an efficient OLED since the light needs to escape the device. A device is composed of a stack of several layers of organic semiconductor materials, each possessing different refractive indices, sandwiched between two electrodes. Depending on the angle of emission

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• conventional 2D materials have a wide bandgap that requires UV light irradiation for their activation. Since 94% of the rays from the sun are not sufficient to activate these conventional semiconductor materials, many strategies have been proposed to design photocatalysts that can harvest in a wide spectrum of

• black phosphorus (BP), the most stable allotrope of phosphorus, has been shown as a highly efficient photocatalyst possessing superior features in many respects [36][37]. BP, a vital semiconductor 2D material with excellent physicochemical properties such as high carrier mobility, tunable optical

Photoredox catalysis in nickel-catalyzed C–H functionalization

• Lusina Mantry,
• Rajaram Maayuri,
• Vikash Kumar and
• Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

• carbon nitride (mpg-CN) [74][75][76] as a heterogeneous organic semiconductor photocatalyst in combination with nickel catalysis [77]. Here, the catalytic system consisting of NiBr2·glyme, 2,2′-bipyridine, 2,6-lutidine, and mpg-CN under blue light irradiation at ambient temperature was found to be

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• compounds having semiconductor properties [80]. The syntheses of these compounds were studied by Janosik in 2006. The N-silyl-protected 3-bromoindole 93 was subjected to strong basic medium (t-BuLi) at low temperature and then quenched with either bis(phenylsulfonyl)sulfide (83) or indole disulfide 94

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• [11][12], the 2,2’-bianthracene derivative 3 provides a green and fluorescent OLED [13], 2,2’-bianthracenyl (4) has been employed as an organic semiconductor in an OFET device [14], and di-n-alkoxyanthracenes have gelling properties with diverse solvents, mainly alkanes and alcohols [4]. Furthermore

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• researchers in semiconductor materials has covered the field of organic electronics. The advantages of organic oligomeric and polymeric materials for applications in OFET and thin-film transistor (TFT) technologies are due to the ease of their directed chemical modification, mechanical flexibility, the

• characteristics of OFETs based on compounds 45 showed almost complete absence of a dependence of the semiconductor properties (μe = 0.08–0.01 cm2⋅V−1⋅s−1) on the structure of the alkyl substituent at the nitrogen atom. It was only established that the distancing of the branching position of the alkyl chain

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• . Post-modifications of hydrogels propose an attractive platform so that a variety of fresh functions, which are not arising from initial monomers, could be accessible on a parental network. Photoinduced post-modification of hydrogels by embedding semiconductor nanosheets would be of high interest and

• novelty. Here, a metal-free semiconductor graphitic carbon nitride (g-CN)-embedded hydrogel as an initial network was synthesized via redox-couple initiation under dark conditions. Post-photomodification of so-formed hydrogel, thanks to the photoactivity of the embedded g-CN nanosheets, was exemplified in

• -sustainable semiconductors are slowly being replaced by a new generation of semiconductors. Graphitic carbon nitride (g-CN) is a metal-free polymeric semiconductor that is mainly composed of carbon and nitrogen elements by tri-s-triazine, triazine imide, or heptazine repeating units [16][17][18]. g-CN

Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds

• Guanglong Pan,
• Qian Yang,
• Wentao Wang,
• Yurong Tang and
• Yunfei Cai

Beilstein J. Org. Chem. 2021, 17, 1171–1180, doi:10.3762/bjoc.17.89

• .17.89 Abstract A visible light-mediated heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile has been established using K-modified carbon nitride (CN-K) as a recyclable semiconductor photocatalyst. This protocol, employing readily accessible alkyl N-hydroxyphthalimide (NHPI

• conditions. Recently, we demonstrated K-modified carbon nitride (CN-K), a semiconductor material, exhibited a remarkably enhanced photocatalytic activity in the decarboxylative Giese reaction. The effect was due to its K-intercalated poly(heptazine)-based structure existing as small lamellar nanocrystallites