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

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

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• ). Convenient control over the structure and function of organic nanocrystals can enhance their utility in new and developed technologies. Keywords: aromatic amphiphiles; exciton diffusion; organic nanocrystals; perylene diimides; self-assembly; Introduction Semiconductor and metal nanoparticles exhibit size

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• reaction; optoelectronic properties; S,N-heteroacene; structure–property relationship; Introduction Thienoacenes and related S,N-heteroacenes have been developed to important π-conjugated systems mainly for application as p-type semiconductor in organic electronic devices with excellent results [1][2][3

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

Synthesis of 6,13-difluoropentacene

• Matthias W. Tripp and
• Ulrich Koert

Beilstein J. Org. Chem. 2020, 16, 2136–2140, doi:10.3762/bjoc.16.181

• significant effect on the molecular shape, is fluorination [5]. Suzuki et al. showed in 2004 the strong effect of perfluorination on the electronic properties [6]. While unsubstituted pentacene (1, PEN, Figure 1) is known to be a p-type semiconductor, the perfluorinated counterpart perfluoropentacene (2, PFP

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

• photocatalytic decomposition of water on illuminated titanium dioxide (TiO2) electrodes in 1972 [27]. This critical report began the field of semiconductor HPC, and in combination with the development of organic electronics, established fundamental principles that still underpin much of the cutting-edge

• components in the coating, leaving the TiO2 powder exposed [75]. In 1938, Goodeve and Kitchener used this knowledge to perform the first study on the photodegradation of organic dyes with TiO2 powder [76]. A series of subsequent reports that were historically relevant to developing TiO2- and semiconductor

• with TiO2 as a model system for metal oxide and inorganic semiconductor HPCats. 2.1 Inorganic semiconductor photocatalysis Semiconductors are defined as materials that have a conductivity between that of an insulator and a conductor [77]. The origin of conductivity is based on the quantum states of

Aryl-substituted acridanes as hosts for TADF-based OLEDs

• Naveen Masimukku,
• Dalius Gudeika,
• Oleksandr Bezvikonnyi,
• Ihor Syvorotka,
• Rasa Keruckiene,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

• active area of the obtained devices was 3 × 6 mm2, furthermore measurement was made after the creation of the device, in the air without passivation. The luminance voltage and current density voltage dependencies were measured with a brightness and semiconductor parameters analyzer (HP 4145A) using a

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

• III. Particularly, an additional substituent at the meso-position introduces more freedoms to functionalize such materials to obtain an absorption being tailor made with respect to the light source applied. This can be a semiconductor laser [14][15][16][18][19][20] or high-power NIR-LED [65] with

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

• Panagiotis S. Gritzapis,
• Panayiotis C. Varras,
• Nikolaos-Panagiotis Andreou,
• Katerina R. Katsani,
• Konstantinos Dafnopoulos,
• George Psomas,
• Zisis V. Peitsinis,
• Alexandros E. Koumbis and
• Konstantina C. Fylaktakidou

Beilstein J. Org. Chem. 2020, 16, 337–350, doi:10.3762/bjoc.16.33

• one of the residual fragments produced by the N–O homolytic cleavage is a carboxylic or a sulfonic acid, generated upon hydrogen abstraction from the corresponding oxygen centred radicals, carbonyloxyl and sulfonyloxyl, respectively. Some are used in the field of photoresists for semiconductor

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• ). Captivatingly, in the absence of a photoredox catalyst, poor yields were obtained, and no reoxidation happened. On the other hand, quite recently, the same group reported on the conversion of phenol derivatives using dual semiconductor photoredox catalysis for C–H bond functionalizations, which was proved to be

• a more sustainable procedure [88] in comparison to previously reported methods [89][90][91][92]. These semiconductor photocatalysts were better because they were: (i) cheap, (ii) easily separable from the reaction mixture, (iii) compatible with other transition metals, and (iv) provided steady

• reaction conditions. Similar to Scheme 2, there was no product obtained without a semiconductor photocatalyst. Therein, they utilized the efficient photoredox catalysts 16 (band gap: 2.4 eV) and 17 (band gap: 2.6–3.0 eV). However, better results were obtained with a heterogeneous semiconductor, photoredox

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

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• voltage (Voc). Indeed, in DSSCs the Voc is determined by the quasi-Fermi-level of the metal oxide semiconductor, which is correlated with its CB edge and electron density (see Figure 7). Solar cells fabricated with various amount of tBP in the electrolyte were investigated (see Table S1 in Supporting

N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe³⁺ sensing

• Jia Gao,
• Ming-Xue Wu,
• Dihua Dai,
• Zhi Cai,
• Yue Wang,
• Wenhui Fang,
• Yan Wang and
• Ying-Wei Yang

Beilstein J. Org. Chem. 2019, 15, 1262–1267, doi:10.3762/bjoc.15.123

• ) as a rising star in fluorescent nanomaterials have attracted wide attention in terms of preparation and application [1][2][3][4]. Fluorescent C-dots possess advantages over organic dyes and traditional semiconductor quantum dots due to their high solubility, facile modification, desirable chemical

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

• limiting factor regarding the packing of molecules. Here we show that the attractive part of the van der Waals potential can be similarly decisive. For the semiconductor surface Si(001), an already covalently bonded molecule of cyclooctyne steers a second incoming molecule via dispersion interactions onto

• 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

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• 1 by replacing reductases with semiconductor photosensitizers and molecular photosensitizers. For example, we reported an ultraviolet-light-driven system using titanium dioxide (TiO2) semiconductor [95][96][97][98][99][100][101]. The conductive band electron of TiO2 (Ered = −0.5 V vs NHE in neutral

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

• hole injection-semiconductor bilayer for solution processing of subsequent layers. The monomers used in this work, 3,4-ethylenedioxythiophene (EDOT) and 3,4-ethylenedithiothiophene (EDTT), were either purchased commercially or prepared according to literature procedures [10]. Both were chosen due to

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

Graphitic carbon nitride prepared from urea as a photocatalyst for visible-light carbon dioxide reduction with the aid of a mononuclear ruthenium(II) complex

• Kazuhiko Maeda,
• Daehyeon An,
• Ryo Kuriki,
• Daling Lu and
• Osamu Ishitani

Beilstein J. Org. Chem. 2018, 14, 1806–1812, doi:10.3762/bjoc.14.153

• emerging material as an organic semiconductor photocatalyst active for various kinds of reactions such as water splitting, CO2 reduction, and degradation of harmful organic compounds, because of its non-toxic, stable, and earth-abundant nature [2][3][4][5][6][7]. Our group has developed photocatalytic CO2

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• acceptor molecule, than to poly(3-hexylthiophene-2,5-diyl) (P3HT) [107], which is a known donor molecule. It can thus be concluded that TFEO-Pc can play a role as an acceptor-type semiconductor. In general, organic semiconductors have a greater abundance of donor-type molecules than acceptor-type molecules

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• traditional semiconductor quantum dots (QDs). Particularly in the areas of live imaging and drug delivery, due to their water solubility, low toxicity and photo- and chemical stability. Carbohydrates are readily available chiral biomolecules in nature which offer an attractive and cheap starting material from

• fluorescent nanomaterials combined with their myriad of applications, has led to CDs being hailed as the potential non-toxic successors to traditional semiconductor QDs, particularly in the areas of live imaging and drug delivery. Synthetic approaches to access CDs can be classified into two broad categories

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

• Pierre Querard,
• Inna Perepichka,
• Eli Zysman-Colman and
• Chao-Jun Li

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

• Pierre Querard Inna Perepichka Eli Zysman-Colman Chao-Jun Li Department of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• . Specifically, this improves the extraction rate of holes at the anode interface. An enhanced hole extraction rate at the semiconductor/anode interface will reduce the accumulation of holes near the electrode, thereby preventing the screening of the internal field and suppressing recombination. The reduction of