Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

• Abel Cárdenas,
• Zexin Jin,
• Yong Ni,
• Jishan Wu,
• Yan Xia,
• Francisco Javier Ramírez and
• Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

• , National University of Singapore, 3 Science Drive 3, Singapore, Singapore 10.3762/bjoc.21.20 Abstract Oxidized states of polycyclic aromatic hydrocarbons are of importance as they represent charged conductive species in organic semiconductor substrates. In this work, we investigated the properties of

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• from certain plant species (Figure 1) [12]. The acenaphthylene-fused thiophene-based heteroarene 3 is another heterocyclic fluoranthene analogue, which was used as an organic semiconductor in transistors [13]. The synthesis and coordination complexes of the acenaphthylene-fused N-heterocyclic (NHC

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• field-effect transistor; organic semiconductor; violanthrone; Introduction Recently, organic semiconductors have received considerable attention due to their potential technological applications in semiconductor devices, such as organic field-effect transistors (OFETs) [1][2], organic light-emitting

• , organic semiconductor molecules with large fused conjugated systems have achieved high charge carrier mobility. Such molecular structures improve the intermolecular interactions (such as π–π stacking) that are required to facilitate the hopping of charge carriers between adjacent molecules [7][8][9

Kinetically stabilized 1,3-diarylisobenzofurans and the possibility of preparing large, persistent isoacenofurans with unusually small HOMO–LUMO gaps

• Qian Liu and
• Glen P. Miller

Beilstein J. Org. Chem. 2024, 20, 1099–1110, doi:10.3762/bjoc.20.97

• gaps is achievable. As such, these molecules deserve increased attention as potential p-type organic semiconductors. Keywords: acene; DFT calculation; highly delocalized π-system; isoacenofuran; isobenzofuran; kinetically stabilized; organic semiconductor; small HOMO–LUMO gap; synthesis; Introduction

• hexacene (Figure 3). Thus, pentacene, a benchmark organic semiconductor, has a calculated HOMO–LUMO gap of 2.18 eV, nearly 0.5 eV greater than that of isotetracenofuran (13) with an isoelectronic π-system (22 π-electrons each). The incorporation of phenylthio groups (compound 16) further lowers the HOMO

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• both n- and p-type organic semiconductors [9][10][11][12]. The Würthner and Meijer groups presented an early example of the utility of hydrogen bonding in the fabrication of organic semiconductor devices. A thin-film device architecture was developed consisting of oligo(p-phenylenevinylene) (OPV) and

• DCPQs and DPQDs in this context. Overall, this work contributes to our overarching objective to investigate the influence of hydrogen-bonding functionality on optoelectronic material organization and next-generation organic semiconductor device performance. Experimental General methods Reagents and

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

• 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

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

• )aromatic compounds (Qx53) with a chalcogenodiazolo[3,4-b]pyrazine scaffold. These compounds exhibited narrow bandgaps (from 1.25 to 1.44 eV) and demonstrated n-type organic semiconductor properties [56]. Jin and co-workers focused on improving the charge-transfer characteristics of a semiconducting

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

• , 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

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

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

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

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

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

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

• , g-CN as an organic semiconductor is utilized in polymerization processes as a photoinitiator by generation of reactive radical species (O2−•, HO•, HO2•) under convenient light illumination. The ability of g-CN to initiate polymerization and act as a polymerization locus for a covalent polymer growth

Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

• Dongyang Chen and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 210–223, doi:10.3762/bjoc.17.21

• Dongyang Chen Eli Zysman-Colman Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK 10.3762/bjoc.17.21 Abstract The trifluoromethyl group has been previously explored as a non-conjugated electron-withdrawing group in donor–acceptor

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

• Callum Prentice James Morrisson Andrew D. Smith Eli Zysman-Colman Organic Semiconductor Centre, EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, Scotland, KY16 9ST, United Kingdom Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Macclesfield SK102NA, United

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• electrostatic repulsion that prevents the dye adsorption. 2.2 Organic semiconductor photocatalysis Polyaniline was the first conductive polymer reported by Henry Letheby in 1862 [99][100], but the potential of organic electronics was not realised until the 1960s, and the seminal work of Heeger, MacDiarmid, and

• continuum of bonding and antibonding molecular orbital states which form band structures, analogous with inorganic semiconductors. Hence, the mechanisms of organic semiconductor photocatalysis and the photogeneration of charge carriers is identical to those discussed in the previous section and illustrated

• dependent on the temperature and electronic disorder as each hop requires the reorganisation of the molecules in the chain [115]. A particularly popular organic semiconductor photocatalyst in the recent literature is graphitic carbon nitride (g-C3N4) [23]. g-C3N4 was one of the first synthetic polymers

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

• Daniel R. Sutherland,
• Nidhi Sharma,
• Georgina M. Rosair,
• Ifor D. W. Samuel,
• Ai-Lan Lee and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

• Daniel R. Sutherland Nidhi Sharma Georgina M. Rosair Ifor D. W. Samuel Ai-Lan Lee Eli Zysman-Colman Institute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of

• St Andrews, St Andrews, KY16 9ST, UK Organic Semiconductor Centre, SUPA School of Physics and Astronomy, University of St Andrews, St Andrews, KY16 9SS, UK 10.3762/bjoc.15.285 Abstract Herein, we report a mild and efficient palladium-catalyzed C–H functionalization method to synthesize a series of

• this in mind, we targeted donor (D)–phenylene–acceptor (A) systems that would be of potential interest to the organic semiconductor community. These compounds incorporate strong donors in the form of triphenylamine (TPA) and carbazole (Cz), as can be seen in Scheme 1. Since the corresponding

Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

• Nadezhda S. Demina,
• Nikita A. Kazin,
• Nikolay A. Rasputin,
• Roman A. Irgashev and
• Gennady L. Rusinov

Beilstein J. Org. Chem. 2019, 15, 2678–2683, doi:10.3762/bjoc.15.261

• light-harvesting dyes for dye-sensitized solar cells [1], electron-donating materials for bulk heterojunction solar cells [2][3][4], and p-type semiconductors for organic field-effect transistors [5][6][7]. Within the same context of organic semiconductor development, the bicyclic TT subunit has been

Dispersion-mediated steering of organic adsorbates on a precovered silicon surface

• Lisa Pecher,
• Sebastian Schmidt and
• Ralf Tonner

Beilstein J. Org. Chem. 2018, 14, 2715–2721, doi:10.3762/bjoc.14.249

• accurate results for organic/semiconductor systems in the past [7][8][9][24]. Results and Discussion Bonding and the adsorption path The reactivity of the Si(001) surface is dominated by Si surface dimers with an electronic structure that is well represented by an electrophilic and a nucleophilic Si atom

Synergistic electrodeposition of bilayer films and analysis by Raman spectroscopy

• Saadeldin E. T. Elmasly,
• Luca Guerrini,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Neil J. Findlay,
• Karen Faulds and
• Peter J. Skabara

Beilstein J. Org. Chem. 2018, 14, 2186–2189, doi:10.3762/bjoc.14.191

• containing a de-doped PEDTT layer on top of doped PEDOT is analogous to a solution-processed organic semiconductor layer deposited on top of a PEDOT:PSS layer without the acidic PSS polymer. However, the poor solubility of electrochemically deposited PEDTT (or other electropolymerised potential candidates

Recent advances in materials for organic light emitting diodes

• Eli Zysman-Colman

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

• Eli Zysman-Colman Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK 10.3762/bjoc.14.168 Keywords: organic light emitting diodes; Organic light emitting diodes (OLEDs) are at the cusp of becoming the dominant

• in design, from fluorescent compounds to phosphorescent organometallic complexes to organic thermally activated delayed fluorescence (TADF) molecules, the latter driving tremendous recent excitement within the field of organic semiconductor research. This thematic issue of the Beilstein Journal of