Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

• Roland Löw,
• Talina Rusch,
• Tobias Moje,
• Fynn Röhricht,
• Olaf M. Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175

• 10.3762/bjoc.15.175 Abstract Triazatriangulenium (TATA) and trioxatriangulenium (TOTA) ions are particularly suited systems to mount functional molecules onto atomically flat surfaces such as Au(111). The TATA and TOTA units serve as platforms that absorb onto the surface and form ordered monolayers

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

• even bulk heterojunction solar cells [19][20] or DSSCs [21][22]. In this articl we report an innovative synthetic approach for synthesizing 2,3,5,6-tetramethyl-BODIPY compounds and a way to further functionalize such cores has been developed. The optoelectronic properties of the functional molecules

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• ; mechanochemistry; self-assembly; solvent-free; supramolecular; Introduction In living systems an important aspect is to create complex functional molecules from simpler units by following biomolecular mechanisms [1]. The biological assemblies for living beings are developed from processes of spontaneous self

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• ). However, in general, chromophores do not absorb at such long wavelengths and the photon energy is too low for bond-cleavage reactions to generate (i.e., uncage) functional molecules. For example, the bond-dissociation energy of the weak PhCH2–OPh, linkage is reported to be 52.1 kcal mol−1 [43]. These

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• assembly of the target molecules and thus enhances the ease of preparation of various functional molecules. These processes are considered as “green” because of atom economy and synthetic brevity [52] involved in these reactions [12][53][54]. Additionally, several methods are available to remove palladium

Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

• Ken Tamamoto,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

• synthetic tool for producing functional molecules with a CF2CF2 fragment. Keywords: acid chlorides; cross-coupling; iodoarenes; tetrafluoroethylene fragment; thermally stable zinc reagent; Introduction Recently, much attention has been paid to organic compounds containing a perfluoroalkylene unit, e.g

• ][6]. Notably, organofluorine compounds bearing a tetrafluoroethylene (–CF2CF2–) unit have attracted significant interest as a promising framework for various functional molecules. In the medicinal field, for example, Linclau and co-workers reported the first enantioselective synthesis and the

• here should be a suitable and valuable tetrafluoroethylenating agent for preparing various CF2CF2-containing molecules, thereby providing a powerful and practical synthetic tool in organofluorine chemistry. Functional molecules with CF2CF2-fragment. Recovery yield of 2-Zn in DMF (ca. 0.70 M) after

Synthesis and characterization of π–extended “earring” subporphyrins

• Haiyan Guan,
• Mingbo Zhou,
• Bangshao Yin,
• Ling Xu and
• Jianxin Song

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

• Haiyan Guan Mingbo Zhou Bangshao Yin Ling Xu Jianxin Song Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of Application and Assemble of Organic Functional molecules, Hunan Normal University, Changsha 410081, P. R. China

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• standard method for FimH labeling. As we wish to eventually control bacterial adhesion by crosslinking of functional molecules to the adhesin (FimH), we will in the future utilize alternative labeling chemistry to efficiently target FimH. Experimental Peptides and proteins For photolabeling experiments

Synthesis and stability of strongly acidic benzamide derivatives

• Frederik Diness,
• Niels J. Bjerrum and
• Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

• various organic acids in acetonitrile or water (nr = not reported) [12][13][14]. Examples of functional molecules containing an N-triflylbenzamide. Content (percent) of super acids (0.5 mg/mL) over time (hours) in H3PO4/H2O/MeOH 17:3:20 at 50 °C. Synthesis of the strongly acidic benzamide derivatives

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

• phthalocyanine, which originally acts as an electron donor, will exhibit an electron acceptor property. Thus, it is expected that TFEO-Pcs can be developed as unique functional molecules [41]. This review summarizes the synthesis of various TFEO-Pc derivatives and the effect of fluorine on their properties

Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides

• Ryota Miyaji,
• Yuuki Wada,
• Akira Matsumoto,
• Keisuke Asano and
• Seijiro Matsubara

Beilstein J. Org. Chem. 2017, 13, 1518–1523, doi:10.3762/bjoc.13.151

• enantioselectivities (Scheme 3); both 1k and 1l comprise a substituent ortho to the hydroxy group. These brominated axially chiral benzamides can further be derivatized for the synthesis of functional molecules [64]. To gain insight into the reaction mechanism, the reactions were performed using substrates 1m and 1n

Self-optimisation and model-based design of experiments for developing a C–H activation flow process

• Alexander Echtermeyer,
• Yehia Amar,
• Jacek Zakrzewski and
• Alexei Lapkin

Beilstein J. Org. Chem. 2017, 13, 150–163, doi:10.3762/bjoc.13.18

• ; flow chemistry; process modelling; self-optimisation; Introduction The development of manufacturing processes to produce functional molecules, such as pharmaceuticals or fine chemicals, often relies on experience and trial-and-error, rather than on mechanistic process models [1]. The only reason for

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• development of functional supramolecular materials [4][5][6]. In PRX applications, chemical modification of the threading CDs is important to reduce intermolecular interactions of the PRXs, impart solubility in organic solvents and water, and introduce functional molecules [7][8][9]. In this regard, various

• the terminals of the axle polymers have an attractive designs for the fabrication of biomaterials, because the terminal azide or alkynyl groups in the PRXs can be utilized for the modification of other polymer chains and functional molecules. In general, PRXs comprising an inclusion complex of a

• fluorescence imaging Terminal reactive groups in the PRXs can be utilized in various biomaterials applications, such as the fabrication of cross-linked materials (e.g., hydrogels) [29], direct surface immobilization onto alkyne-immobilized surfaces [30], and the modification of other functional molecules for

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• this case, the primary alkylation adducts might be unstable and undergo heterocyclization reactions (on the synthesis of heterocyclic compounds from azoalkenes and diamines see [54][55][56]). Bishydrazones containing clickable groups (like 3) can be introduced into functional molecules or immobilized

DNA functionalization by dynamic chemistry

• Zeynep Kanlidere,
• Oleg Jochim,
• Marta Cal and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2016, 12, 2136–2144, doi:10.3762/bjoc.12.203

• ][26][27][28]. Similarly, a thiol functionality can be introduced by substitution of the amine group of threoninol and incorporated into the oligonucleotide backbone. The amine and thiol groups can be used for further oligonucleotide functionalization reacting these sites with functional molecules like

• metal ligands or fluorophores. Functional molecules of interest can be tethered post-synthetically in an irreversible manner as amide or reversibly as imine or thioester. Recent advances in dynamic combinatorial chemistry [29][30][31][32][33][34][35][36][37][38][39][40] have enabled the utilization of

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• Senhua Chen Zhaoming Liu Yayue Liu Yongjun Lu Lei He Zhigang She School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 135 Xin gang West Road, Guangzhou 510275, China Guangdong Province Key Laboratory of Functional Molecules in Oceanic Microorganism, Bureau of Education, Sun Yat

Fluoride-driven ‘turn on’ ESPT in the binding with a novel benzimidazole-based sensor

• Kai Liu,
• Xiaojun Zhao,
• Qingxiang Liu,
• Jianzhong Huo,
• Bolin Zhu and
• Shihua Diao

Beilstein J. Org. Chem. 2015, 11, 563–567, doi:10.3762/bjoc.11.61

• Kai Liu Xiaojun Zhao Qingxiang Liu Jianzhong Huo Bolin Zhu Shihua Diao Key Laboratory of Inorganic-Organic hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University, Tianjin, 300387, China Tianjin Key Laboratory of Structure and Performance for Functional Molecules

A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)

• Youhei Takeda,
• Masato Okazaki,
• Yoshiaki Maruoka and
• Satoshi Minakata

Beilstein J. Org. Chem. 2015, 11, 9–15, doi:10.3762/bjoc.11.2

• by conventional methodologies, would offer us many opportunities not only for creating helicene-based novel functional molecules but also uncovering missing pieces of unique aspects of helicenes. A bibliographic survey about helicenes led us focus on diazahelicenes having a diazene (–N=N–) moiety

• develop oxidative transformations of aromatic amines for the construction of diverse aza-containing π-conjugated functional molecules [27][28][29][30], we have recently discovered an iodine-containing oxidant-induced unusual oxidative rearrangement of BINAMs leading exclusively to U-shaped azaacenes

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

• polystyrene equipped with peripheral triarylamines, which exhibited two sets of reversible redox peaks in the cyclic voltammetry curves. Keywords: carbocation; cross-coupling; dendrimer; dendronized polymer; redox; Introduction Assembling small functional molecules using dendrimers [1] and dendronized

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• colorless form (state A), the absence of FRET would keep the fluorescence alive, showing that the combination of these two functional molecules leads to a photon-driven fluorescence switch. Previously, we have synthesized a fluorescent-photochromic dyad (1, Figure 2) combining a DCM fluorophore (4

Clean and fast cross-coupling of aryl halides in one-pot

• Valerica Pandarus,
• Geneviève Gingras,
• François Béland,
• Rosaria Ciriminna and
• Mario Pagliaro

Beilstein J. Org. Chem. 2014, 10, 897–901, doi:10.3762/bjoc.10.87

• Affording valued biaryls and heterobiaryls, namely ubiquitous chemical moieties in pharmaceuticals, natural products, photoactive species and many other functional molecules, the Suzuki–Miyaura cross-coupling reaction is widely employed by the fine chemicals and pharmaceutical industries [1]. The reaction

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• developed resulting in a steady increase in life expectancy [2]. All these advances have been enabled by the curiosity of generations of scientists constantly searching for new solutions to the assembly of functional molecules. Importantly this has required the development of several new methods for

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

• M. B. Avinash,
• K. V. Sandeepa and
• T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

• realized by modulating the chemical functionality of interlinking amino acids. Keywords: amino acids; charge transfer; designer functional molecules; molecular assembly; molecular recognition; Findings Geometric shapes, size and patterns have attracted the inquisitive human mind since time immemorial [1

• functional molecules are believed to pave the way for programmable molecular assemblies with advanced applications. Molecular structures of donor–acceptor–donor traids. The red colouring highlights the topological symmetry of NDI and pyrene. (a) UV–vis and (b) fluorescence spectra of 1 (200 μM) in aqueous

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• are excellent candidates to promote aromatic–aromatic interaction in water to form hydrogels, this work contributes to the development of functional molecules that have dual or multiple roles and ultimately may lead to new molecular hydrogels of therapeutic agents for topical use. Keywords: self

Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization

• Ryan Pearson,
• Shuyu Zhang,
• Gang He,
• Nicola Edwards and
• Gong Chen

Beilstein J. Org. Chem. 2013, 9, 891–899, doi:10.3762/bjoc.9.102

• ; palladium; phenanthridine; picolinamide; Introduction Phenanthridines and 5,6-dihydro-phenanthridines are important core structures found in a variety of natural products and functional molecules (Scheme 1A) [1][2][3][4][5][6][7][8]. Synthetic methods for their preparation include the classical Pictet