My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• field of supramolecular chemistry, specifically, and organic materials, broadly. My research group’s efforts toward designing new sensors based on small molecule gelators are described. In particular, I highlight how our design strategy has evolved as we learn more about molecular gelators. This

• perspective concludes with some predictions about where molecular gels, as well as my personal and professional life, are headed. Keywords: molecular gel; organic chemistry; organic materials; self-assembly; supramolecular chemistry; Review One of my earliest memories involves pouring water down our

• a great mentor who knew exactly when to push, when to provide assistance, and when to disappear and let me figure it out on my own. A fortuitous and unusual observation during my graduate work led me into the field of organic materials: I observed an enolate alkylation wherein the rate correlated

A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

• Xinlong Pang,
• Chao Chen,
• Ming Li and
• Chanjuan Xi

Beilstein J. Org. Chem. 2015, 11, 2365–2369, doi:10.3762/bjoc.11.258

• : benzimidazo[1,2-c]quinazoline; (bromophenyl)iodonium salt; copper catalyst; o-cyanoaniline; quinazolin-4(3H)-imine; Ullmann N-arylation; Introduction Nitrogen-containing heterocycles are ubiquitous backbones in natural products, medicine and organic materials. In addition, they are also important ligands for

Tuning the size of a redox-active tetrathiafulvalene-based self-assembled ring

• Sébastien Bivaud,
• Sébastien Goeb,
• Vincent Croué,
• Magali Allain,
• Flavia Pop and
• Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 966–971, doi:10.3762/bjoc.11.108

• its size, and illustrating the high potential of the coordination-driven approach in tuning the size and the shape of a target cavity. This approach constitutes a promising strategy to address the design of organic materials (e.g. for organic photovoltaics or molecular electronic devices). Indeed

• , mastering the geometry of multicomponent redox-active systems offers a unique opportunity to fine-tuning electronic interactions within the material [43], an issue which is of prime importance for optimizing electron transport in organic materials. X-ray crystal structures of: (a) ligand L1, (b) self

Copper ion salts of arylthiotetrathiafulvalenes: synthesis, structure diversity and magnetic properties

• Longfei Ma,
• Jibin Sun,
• Xiaofeng Lu,
• Shangxi Zhang,
• Hui Qi,
• Lei Liu,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 850–859, doi:10.3762/bjoc.11.95

• : antiferromagnetic interaction; arylthio-substituted tetrathiafulvalenes; charge-transfer; crystal structure; magnetic property; Introduction Since firstly synthesized in 1970s [1], tetrathiafulvalene (TTF) and its derivatives have been intensively studied to explore functional organic materials [2]. Inspired by

Redox active dendronized polystyrenes equipped with peripheral triarylamines

• Toshiki Nokami,
• Naoki Musya,
• Tatsuya Morofuji,
• Keiji Takeda,
• Masahiro Takumi,
• Akihiro Shimizu and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2014, 10, 3097–3103, doi:10.3762/bjoc.10.326

• tetrathiafulvalene (TTF) derivatives [15][16][17][18][19], the corresponding dendronized polymers are rare [20]. One of the major reasons for this seems to be the difficulty in making such structures. However, redox-active dendronized polymers should provide more opportunities to form functional organic materials

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

• Emma Werz Helmut Rosemeyer Organic Materials Chemistry and Bioorganic Chemistry, Institute of Chemistry of New Materials, University of Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany Ionovation GmbH, Westerbreite 7 (CUT), D-49084 Osnabrück, Germany 10.3762/bjoc.10.240 Abstract The article

Carbon nanomaterials

• Anke Krueger

Beilstein J. Org. Chem. 2014, 10, 1785–1786, doi:10.3762/bjoc.10.186

• and many carbon-rich organic materials are available to the scientific community in excellent quality and suitable amounts for the investigation of fundamental properties and prospective applications. This has led to the emergence of a new community of scientists working in an interdisciplinary area

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• Anastasia S. Kostyuchenko Vyacheslav L.Yurpalov Aleksandra Kurowska Wojciech Domagala Adam Pron Alexander S. Fisyuk Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russia Laboratory of New Organic Materials, Omsk State Technical University, Mira

Direct C–H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

• Ren Tomita,
• Yusuke Yasu,
• Takashi Koike and
• Munetaka Akita

Beilstein J. Org. Chem. 2014, 10, 1099–1106, doi:10.3762/bjoc.10.108

• pharmaceuticals and agrochemicals as well as functional organic materials. But reported synthetic methods usually require multiple synthetic steps and/or exhibit limitation with respect to access to tri- and tetrasubstituted CF3-alkenes. Thus development of new methodologies for facile construction of Calkenyl

• catalysis; radical reaction; trifluoromethylation; Introduction The trifluoromethyl (CF3) group is a useful structural motif in many bioactive molecules as well as functional organic materials [1][2][3][4][5][6]. Thus, the development of new methodologies for highly efficient and selective incorporation of

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

• Sarah Bay,
• Gamall Makhloufi,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

• approximation. Keywords: absorption spectroscopy; cyclic voltammetry; chromophores; fluorescence; multicomponent reactions; photo-induced electron transfer; Introduction Chromophores, fluorophores, and electrophores, are functional organic materials [1] and constitute active components in molecular

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

• Christian Muschelknautz,
• Robin Visse,
• Jan Nordmann and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51

• reactions; Introduction Functional organic materials [1], such as chromophores, fluorophores, and electrophores, constitute the active components in molecular electronics [2], photonics [3], and bioanalytics [4][5][6]. Among many chromophores the class of merocyanines [7][8][9], i.e. α-donor-ω-acceptor

Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions

• Phei Li Lau,
• Ray W. K. Allen and
• Peter Styring

Beilstein J. Org. Chem. 2013, 9, 2886–2897, doi:10.3762/bjoc.9.325

• these cross-coupling methods has undoubtedly revolutionalised the protocols for the construction of natural products, building blocks for supramolecular chemistry, self-assembly of organic materials and polymers, and lead compounds in medicinal chemistry from simpler entities [1]. These include the

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

• Christina Lohoelter,
• Malte Brutschy,
• Daniel Lubczyk and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317

• . The advantage of HFF-QCMs is the low detection limit and the fast, highly reproducible and easy to apply electro spray protocol for the coating of such devices [57][58][59]. Almost all organic materials which show at least a certain solubility in tetrahydrofuran or other volatile organic solvents

• precursor all-syn-16 in hands and the need for organic materials with pronounced cavities as potent affinity materials we envisioned the synthesis of a capsule-type architecture. Therefore, all-syn-16 was O-alkylated by treatment with 5-bromo-1-pentene using standard conditions [70] to yield the

3-Pyridinols and 5-pyrimidinols: Tailor-made for use in synergistic radical-trapping co-antioxidant systems

• Luca Valgimigli,
• Daniele Bartolomei,
• Riccardo Amorati,
• Evan Haidasz,
• Jason J. Hanthorn,
• Susheel J. Nara,
• Johan Brinkhorst and
• Derek A. Pratt

Beilstein J. Org. Chem. 2013, 9, 2781–2792, doi:10.3762/bjoc.9.313

• important class of compounds used to protect organic materials from oxidative degradation from autoxidation (Scheme 1) [1][2]. Phenolic compounds are almost universally used for this purpose – for industrial/commercial applications as well as in nature – since they possess inherently high reactivities to

Crystal design using multipolar electrostatic interactions: A concept study for organic electronics

• Peer Kirsch,
• Qiong Tong and
• Harald Untenecker

Beilstein J. Org. Chem. 2013, 9, 2367–2373, doi:10.3762/bjoc.9.272

• transport in organic materials, or electron transport in general, occurs in most cases by a hopping mechanism which is described by the Marcus theory [6]. According to Marcus’ formula (1), the rate of electron transfer (ket) between equal molecules is controlled by the electronic overlap (transfer integral

Organo-fluorine chemistry III

• David O'Hagan

Beilstein J. Org. Chem. 2013, 9, 2180–2181, doi:10.3762/bjoc.9.255

• contributions in the Thematic Series focus on this aspect of organo-fluorine chemistry. Fluorine touches all categories of performance compounds extending from bioactives to organic materials, and society demands continual improvements in the quality and performance of products and devices. As the global

Cyclization of substitued 2-(2-fluorophenylazo)azines to azino[1,2-c]benzo[d][1,2,4]triazinium derivatives

• Aleksandra Jankowiak,
• Emilia Obijalska and
• Piotr Kaszynski

Beilstein J. Org. Chem. 2013, 9, 1873–1880, doi:10.3762/bjoc.9.219

• Aleksandra Jankowiak Emilia Obijalska Piotr Kaszynski Organic Materials Research Group, Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA Faculty of Chemistry, University of Łódź, Tamka 12, 91403 Łódź, Poland 10.3762/bjoc.9.219 Abstract Light-induced cyclization of several

• cyclization of fluorides II (Figure 1) in the presence of Ca2+ ions [7]. A further progress in the investigation of cation 1a and its applications as a pharmacophore or a component of organic materials requires access to functionalized derivatives, in which substituents control the properties and allow the

Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans

• Yifan Li and
• Jérôme Waser

Beilstein J. Org. Chem. 2013, 9, 1763–1767, doi:10.3762/bjoc.9.204

• organic materials (Figure 1). For example, members of the furocoumarin class of natural products including psoralen (1), 8-methoxypsoralen (2) and angelicin (3) can cross-link with DNA upon light irradiation. They have consequently been used for the treatment of skin diseases such as cancer or psoriasis

• as important structural elements for organic materials, such as the organic transistor 6 [8]. Due to the importance of benzofurans, the discovery of new efficient methods for their synthesis and functionalization is an intensive field of research [9][10][11]. Especially interesting would be methods

Palladium(II)-catalyzed Heck reaction of aryl halides and arylboronic acids with olefins under mild conditions

• Tanveer Mahamadali Shaikh and
• Fung-E Hong

Beilstein J. Org. Chem. 2013, 9, 1578–1588, doi:10.3762/bjoc.9.180

• Substituted olefins are important structural motifs in natural products, pharmaceuticals, bioactive compounds and organic materials [1][2]. Olefins such as stilbene derivatives normally show antitumor [3], antiinflammatory [4], neuroprotective [5], and cardioprotective [6] properties. Due to its importance in

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

• Rohan J. Kumar,
• Jegadesan Subbiah and
• Andrew B. Holmes

Beilstein J. Org. Chem. 2013, 9, 1102–1110, doi:10.3762/bjoc.9.122

• times are required [3]. The use of organic materials in photovoltaic devices is attractive owing to the abundance of the elements used, the possibility to use low-cost manufacturing techniques, and the diversity of molecular structure that is accessible. There is a growing understanding of the control

Zanthoxoaporphines A–C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae)

• Fidelis N. Samita,
• Louis P. Sandjo,
• Isaiah O. Ndiege,
• Ahmed Hassanali and
• Wilber Lwande

Beilstein J. Org. Chem. 2013, 9, 447–452, doi:10.3762/bjoc.9.47

• larvicidal activity were tested at 10, 5, 2, and 1 ppm. This was performed by dissolving 5, 2.5, 1 and 0.5 mg of these organic materials in 1 mL of acetone and adding 499 mL of distilled water in a 500 mL beaker. Each of the prepared solutions was divided into five portions of 100 mL each in 250 mL beakers

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• role in the discovery of active antitumor drugs [29][30][31]. Carbazole derivatives also find applications in organic materials as chromophores and photoconductors [32]. For several years, the development of methodologies concerning indole synthesis and functionalization has been one of the most

Synthesis and characterization of low-molecular-weight π-conjugated polymers covered by persilylated β-cyclodextrin

• Aurica Farcas,
• Ana-Maria Resmerita,
• Andreea Stefanache,
• Mihaela Balan and
• Valeria Harabagiu

Beilstein J. Org. Chem. 2012, 8, 1505–1514, doi:10.3762/bjoc.8.170

• materials with extended π-conjugation have attracted considerable attention in recent years as a new class of active organic materials for optoelectronic applications [1][2][3][4]. Among the conjugated polymers, a number of poly(9-alkylfluorene)s (PFs) and poly(9,9-dioctylfluorene) (PDOF) polymers in

• bulkier silylated groups, affecting the ability of the diborate groups from the DOF molecule to partially penetrate the PS-βCD cavity. Keywords: alternating fluorene-bithiophene copolymer; cyclodextrins; interlocked molecules; macrocycles; persilylated β-cyclodextrin; polyrotaxanes; Introduction Organic

Synthesis of oleophilic electron-rich phenylhydrazines

• Aleksandra Jankowiak and
• Piotr Kaszyński

Beilstein J. Org. Chem. 2012, 8, 275–282, doi:10.3762/bjoc.8.29

• Aleksandra Jankowiak Piotr Kaszynski Organic Materials Research Group, Department of Chemistry, Vanderbilt University, Nashville, TN 37235 Faculty of Chemistry, University of Lódź, Tamka 12, 91403 Lódź, Poland 10.3762/bjoc.8.29 Abstract Phenylhydrazines 1 substituted with two or three long-chain

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• intramolecular charge transfer (ICT) are reviewed. Design, synthetic pathways, linear and nonlinear optical properties, electrochemistry, structure–property relationships, and the prospective application of such D-π-A organic materials are described. This review focuses on Y-shaped imidazoles, bi- and

• made in the development and the investigation of new organic push–pull systems. In contrast to inorganic materials, the advent of dipolar (hetero)organic materials with readily polarizable structure was stimulated by their relative ease of synthesis, well-defined structure, chemical and thermal

• electronic behavior of the appended donors and acceptors and the character and length of the π-conjugated linker [4][5][6][7]. Recently, it was also recognized that push–pull systems applicable as organic materials should possess high chemical and thermal robustness, good solubility in common organic