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

• Shirakawa, leading to their shared award of the 2000 Chemistry Nobel Prize for “the discovery and development of conductive polymers” [101]. For the following 60 years, and still to this day, organic electronics is a vibrant field of research within materials chemistry and physics as a potential source of

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

• Grzegorz Mlostoń,
• Mateusz Kowalczyk,
• André U. Augustin,
• Peter G. Jones and
• Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

• materials chemistry, and electrochemical studies [19]. In continuation of our studies on organic sulfur compounds and the mechanisms of their reactions, the main goal of the present work was the examination of the formal [3 + 2]-cycloaddition reactions of ferrocenyl-substituted thioketones 8 with D–A

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• synthesis of π-extended phospholes. In this respect, our attention focused on the fusion of phosphole with triphenylene, which represents one of the most common disc-like PAH motifs in organic materials chemistry [19][20][21][22][23][24][25]. Herein, we report on the synthesis of triphenylene-fused

Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel–Crafts reaction

• Yafang Dong,
• Masahiko Sakai,
• Kazuto Fuji,
• Kohei Sekine and
• Yoichiro Kuninobu

Beilstein J. Org. Chem. 2020, 16, 409–414, doi:10.3762/bjoc.16.39

• Yafang Dong Masahiko Sakai Kazuto Fuji Kohei Sekine Yoichiro Kuninobu Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga-shi

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

• to the benzoquinone acceptor. Compound 3, where benzoquinone is para-conjugated to the diphenylamine donor group, exhibited thermally activated delayed fluorescence (TADF) with a biexponential lifetime characterized by a prompt ns component and a delayed component of 353 μs. Keywords: materials

• chemistry; physical organic chemistry; spectroscopy; thermally activated delayed fluorescence; Introduction Substituted benzoquinones and derivatives [1] have generated great interest, in particular due to their redox-active nature and their importance in biological mechanisms [2]. Compounds bearing

Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene

• Luna Kono,
• Yuma Nakagawa,
• Ayako Fujimoto,
• Ryo Nishimura,
• Yohei Hattori,
• Toshiki Mutai,
• Nobuhiro Yasuda,
• Kenichi Koizumi,
• Satoshi Yokojima,
• Shinichiro Nakamura and
• Kingo Uchida

Beilstein J. Org. Chem. 2019, 15, 2204–2212, doi:10.3762/bjoc.15.217

• Luna Kono Yuma Nakagawa Ayako Fujimoto Ryo Nishimura Yohei Hattori Toshiki Mutai Nobuhiro Yasuda Kenichi Koizumi Satoshi Yokojima Shinichiro Nakamura Kingo Uchida Department of Materials Chemistry, Ryukoku University, Seta, Otsu, Shiga 520-2194, Japan Department of Materials and Environmental

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic

• combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes

• (and dynamic) under mild conditions at 25–50 °C (Scheme 18) [189]. At lower temperatures (−10 to 0 °C) the reaction was considerably slower, but overall suggests that certain fulvene DACs can be applied in DCC. Materials chemistry Despite their reactive nature, fulvenes have been successfully used in

Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes

• Muhammad Israr,
• Changqing Ye,
• Munira Taj Muhammad,
• Yajun Li and
• Hongli Bao

Beilstein J. Org. Chem. 2018, 14, 2916–2922, doi:10.3762/bjoc.14.270

• research and synthesis of functionalized compounds that have applications in medicinal chemistry, drug discovery, materials chemistry, and as well as in bioconjugates [2][3][4][5][6][7][8][9][10][11][12]. The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction [13][14][15][16][17][18][19][20][21

Copolymerization of epoxides with cyclic anhydrides catalyzed by dinuclear cobalt complexes

• Yo Hiranoi and
• Koji Nakano

Beilstein J. Org. Chem. 2018, 14, 2779–2788, doi:10.3762/bjoc.14.255

• Yo Hiranoi Koji Nakano Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan 10.3762/bjoc.14.255 Abstract The alternating copolymerization of epoxides with cyclic anhydrides (CAs) is a highly diverse

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

• Henrike Ehrhorn,
• Janin Schlösser,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

• metallacyclobutadiene (MCBD) intermediates [12]. Ongoing progress in the development of highly active homogeneous alkyne metathesis catalysts (Figure 1) has increased the value of this method in natural product and materials chemistry. The contributions from our group to the development of alkyne metathesis catalysts

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

• obtained his Ph.D. from McGill University in 2003. He then completed two postdoctoral fellowships, one in supramolecular chemistry at the Organic Chemistry Institute, University of Zurich and the other in inorganic materials chemistry at Princeton University. After beginning his career in Canada, he moved

Strong binding and fluorescence sensing of bisphosphonates by guanidinium-modified calix[5]arene

• Jie Gao,
• Zhe Zheng,
• Lin Shi,
• Si-Qi Wu,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2018, 14, 1840–1845, doi:10.3762/bjoc.14.157

• Jie Gao Zhe Zheng Lin Shi Si-Qi Wu Hongwei Sun Dong-Sheng Guo College of Chemistry, Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Nankai University, Tianjin 300071, China Collaborative Innovation Center of Chemical Science and Engineering, Nankai University

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

• Grzegorz Mlostoń,
• Katarzyna Urbaniak,
• Paweł Urbaniak,
• Anna Marko,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

• thiophenyl substituents may be of importance for their applications in materials chemistry. Experimental General information: Solvents and chemicals were purchased and used as received without further purification. Products were purified by standard column chromatography on silica gel (230–400 mesh, Merck

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

• Alberto Spinella,
• Marco Russo,
• Antonella Di Vincenzo,
• Delia Chillura Martino and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

• ; solid-state NMR; Introduction Nanosponges (NSs) [1][2][3] constitute an emerging area of both materials chemistry and supramolecular chemistry due to their peculiar properties, which have been object of an increasing interest during the last years. These materials are constituted by hyper-reticulated

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• . Mechanochemistry has also found recent attention in materials chemistry and API formulation during which rearrangement of non-covalent interactions give rise to functional products. However, this has been known to nucleic acids science almost since its inception in the late nineteenth century when Miescher

• elements of the subject relevant to the current work including applications in organic synthesis [5][6][7][8], green chemistry [9], API formulation [10] and coordination/materials chemistry [11][12]. Some aspects of the current work have also been reviewed recently [13]. However, the impact of

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

• Takeshi Fujita,
• Ryo Kinoshita,
• Tsuyoshi Takanohashi,
• Naoto Suzuki and
• Junji Ichikawa

Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266

• promoted HI elimination to afford ring-difluorinated dibenzo[a,c][7]annulene 7a in an almost quantitative yield. Since dibenzo[a,c][7]annulenes serve as bioactive agents, this method would be of value in the research directed toward pharmaceutical and materials chemistry [33][34][35]. Conclusion In summary

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

• Grzegorz Mlostoń,
• Paulina Pipiak,
• Róża Hamera-Fałdyga and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 1900–1906, doi:10.3762/bjoc.13.185

• ethenes form an important class of organic compounds with a growing number of applications in materials chemistry, crystal engineering, photooptics, etc. Among these, the thiophen-2-yl-substituted ethenes [1][2][3][4][5] as well as dibenzofulvenes-containing compounds [6][7][8][9] are of special interest

• of trimethylsilylated thiofluorenone S-methanide with aryl and hetaryl thioketones can also be used for this transformation. The described protocol opens a new, straightforward access to a series of new dibenzofulvenes [7] containing hetaryl rings, which can be of great interest in materials

• chemistry and related sciences. The key intermediate in the reaction is the 1,3-dithiolane carbanion, which, in contrast to the 4,5-unsubstituted analogues, undergoes a spontaneous cycloreversion reaction to give tetraarylethene and dithioformate anion. This method supplements the list of preparatively

Solvent-free sonochemistry: Sonochemical organic synthesis in the absence of a liquid medium

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 1850–1856, doi:10.3762/bjoc.13.179

• others [7]. Ultrasonic irradiation is commonly carried out on liquid/gas mixtures (for gas removal), liquid/liquid mixtures and liquid/solid mixtures. The technique is used extensively in materials chemistry, for example, it has been demonstrated to be one of the most efficient methods to exfoliate

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

• A. Michael Downey and
• Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

• glycosylations have now even been described in materials chemistry. Here they provide an extremely efficient way to functionalize hydroxy-terminated self-assembled monolayers (SAM) on gold (Scheme 37). First the surface was incubated with divinyl sulfone (DVS) in a basic aqueous buffer (pH 11) followed by

Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides

• Ilya V. Efimov,
• Marsel Z. Shafikov,
• Nikolai A. Beliaev,
• Natalia N. Volkova,
• Tetyana V. Beryozkina,
• Wim Dehaen,
• Zhijin Fan,
• Viktoria V. Grishko,
• Gert Lubec,
• Pavel A. Slepukhin and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2016, 12, 2390–2401, doi:10.3762/bjoc.12.233

• -5-substituted isoxazoles that are otherwise difficult to obtain. Keywords: β-azolyl enamine; [3 + 2]-cycloaddition; isoxazole; isoxazoline; nitrile oxide; Introduction The biological activity and technically useful properties of isoxazoles have made them the focus of both medicinal and materials

• chemistry over the years [1]. Isoxazoles have been found in natural products [1], and they exhibit anticancer [2], antiviral [1], anti-inflammatory [3], antidiabetic [4], anti-Alzheimer [5] and many other types of biological activity [6]. Isoxazolines and isoxazoles have been applied as chemosensors, liquid

Synthesis of ferrocenyl-substituted 1,3-dithiolanes via [3 + 2]-cycloadditions of ferrocenyl hetaryl thioketones with thiocarbonyl S-methanides

• Grzegorz Mlostoń,
• Róża Hamera-Fałdyga,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2016, 12, 1421–1427, doi:10.3762/bjoc.12.136

• thiocarbonyl S-methanides. On the other hand, ferrocenyl-substituted 1,3-dithiolanes can be of interest for materials chemistry and for electrochemical studies [11]. The goal of the present study was to examine reactions of selected ferrocenyl hetaryl thioketones 1 with aromatic and cycloaliphatic thiocarbonyl

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• Minh Anh Truong Koji Nakano Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan 10.3762/bjoc.12.79 Abstract Ladder-type π-conjugated compounds containing a benzo[2,1-b:3,4-b']difuran skeleton, such

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• with Mo and Ru catalysts has become a very practical methodology in organic, polymer and materials chemistry. ROMP is also the method of choice for obtaining new and diverse metallopolymers [31][32][33][34]. The present contribution aims to provide an overview of selected developments in metathesis

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• the fields of supramolecular and materials chemistry due to their great potential application in molecular electronics, for example, as switches and conductors [10][11][12][13][14]. As we all know, TTF derivatives can form charge transfer (CT) complexes with electron acceptors such as

Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers

• Davide Bello and
• David O'Hagan

Beilstein J. Org. Chem. 2015, 11, 1902–1909, doi:10.3762/bjoc.11.205

• Organofluorine compounds have found wide use in tuning the properties of performance compounds in medicinal and materials chemistry [1][2]. Also the electronegativity of fluorine has been used to design and tune steric and electronic mimetics of functional groups for applications in biomolecular chemistry. For