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

Synthesis of trifunctional cyclo-β-tripeptide templates

• Frank Stein,
• Tahir Mehmood,
• Tilman Plass,
• Javid H. Zaidi and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2012, 8, 1576–1583, doi:10.3762/bjoc.8.180

• hydrazide linker [11]. Together with a convenient and efficient purification procedure, this method is beneficial with respect to yield and speed of the synthesis. Further, an orthogonal protection strategy was introduced to equip the β-peptide template with three different functional molecules allowing

Syntheses and applications of furanyl-functionalised 2,2’:6’,2’’-terpyridines

• Jérôme Husson and
• Michael Knorr

Beilstein J. Org. Chem. 2012, 8, 379–389, doi:10.3762/bjoc.8.41

• important requirement for sensitizers to be used in DSSC [6]. Conclusion This short review demonstrates that the combination of the furan heterocycle and the terpyridine ligand leads to a series of quite versatile functional molecules. The attached furan ring serves mainly as a precursor to carboxylic acid

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• well as in increasing solubility [20]. Moreover, triazoles can function as attractive linker units which could connect two pharmacophores to give an innovative bifunctional drug, and thus have become increasingly useful and important in constructing bioactive and functional molecules [21][22][23

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

• Benito Alcaide and
• Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73

• functional molecules, and therefore, their stereocontrolled synthesis remains an important research area. On the other hand, the recent resplendent age of gold has been accompanied by the emergence of iron salts as powerful alternatives in view of their inexpensiveness and environmental friendliness [38][39

Expanding the gelation properties of valine-based 3,5-diaminobenzoate organogelators with N-alkylurea functionalities

• Hak-Fun Chow and
• Chin-Ho Cheng

Beilstein J. Org. Chem. 2010, 6, 1015–1021, doi:10.3762/bjoc.6.114

• Hak-Fun Chow Chin-Ho Cheng Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR The Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR Institute of Molecular Functional Materials, Areas of Excellence Scheme

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• gold substrates to solutions of sulfur functionalized molecules [7][8][9][10][11][12][13][14]. These “alligator-clips” [15][16][17] are able to bind functional molecules covalently to gold{111}-surfaces. Phenyl derivatives [18][19], conjugated bi- [18][20] and oligophenyls [18][20][21], oligothiophenes

The C–F bond as a conformational tool in organic and biological chemistry

• Luke Hunter

Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38

• conformational tool for the synthesis of shape-controlled functional molecules. This review will begin by describing some general aspects of the C–F bond and the various conformational effects associated with C–F bonds (i.e. dipole–dipole interactions, charge–dipole interactions and hyperconjugation). Examples

• of functional molecules that exploit these conformational effects will then be presented, drawing from a diverse range of molecules including pharmaceuticals, organocatalysts, liquid crystals and peptides. Keywords: conformation; functional molecules; organofluorine chemistry; stereochemistry

• on examples of shape-controlled functional molecules that exploit the C–F bond as a conformational tool. Bioactive small molecules Despite being the most abundant halogen in the Earth’s crust, fluorine is almost completely absent from natural products chemistry [16]. However, in contrast to the

Diels- Alder reactions using 4,7-dioxygenated indanones as dienophiles for regioselective construction of oxygenated 2,3-dihydrobenz[f]indenone skeleton

• Natsuno Etomi,
• Takuya Kumamoto,
• Waka Nakanishi and
• Tsutomu Ishikawa

Beilstein J. Org. Chem. 2008, 4, No. 15, doi:10.3762/bjoc.4.15

• applicable to not only synthesis of other natural product but also preparation of newly designed functional molecules. The structure of kinamycins. Selected HMBC correlations (lines) and NOE enhancements (dash) on 21 (a) and on 22 (b). Selected HMBC correlations (a) and NOE enhancements (b) on the ring

Aroylketene dithioacetal chemistry: facile synthesis of 4-aroyl- 3-methylsulfanyl- 2-tosylpyrroles from aroylketene dithioacetals and TosMIC

• H. Surya Prakash Rao and
• S. Sivakumar

Beilstein J. Org. Chem. 2007, 3, No. 31, doi:10.1186/1860-5397-3-31

• possible. [3] Since alkylsulfanyl groups are good leaving groups, subsequent to the attack of a nucleophile, one of the alkylsulfanyl groups of the intermediate leave to regenerate the conjugated system. Being polarized alkenes the AKDTAs also react with bi-functional molecules having nucleophilic and