Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• ; found: C, 83.4; H, 5.2; N, 10.8; MS (ESI+, m/z): 402 (100, MH+), 403 (30%). Molecular structure and numbering scheme of 4′-(1-azulenyl)-2,2′:6′,2″-terpyridine (4a, left) and 4′-(1-(4,6,8-trimethyl-azulenyl)-2,2′:6′,2″-terpyridine (4b, right). Packing diagram for 4a showing the π–π stacking and CH–π

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• molecular structure and properties of the conjugated molecules with BDT core, we report here a series of A–π–D–π–A-type conjugated molecules with a regioregular oligo(3-hexylthiophene) chain as the π-bridge unit. The optical and electrochemical properties of these compounds were systematically investigated

On the cause of low thermal stability of ethyl halodiazoacetates

• Magnus Mortén,
• Martin Hennum and
• Tore Bonge-Hansen

Beilstein J. Org. Chem. 2016, 12, 1590–1597, doi:10.3762/bjoc.12.155

• stability of diazo compounds is highly influenced by the α-substituents present in their molecular structure. A simplified illustration of the thermal stabilities for some selected classes of diazo compounds is shown in Figure 1. Aliphatic, non-stabilized diazo compounds are thermally labile and usually

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

• Carl J. Mallia,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1503–1511, doi:10.3762/bjoc.12.147

• by Cross et al. (Figure 2) [18]. The molecular structure of 1 comprises of a palladium atom with near perfect square planar geometry with a slight out of plane displacement of Br and C(1) where the Br–Pd–C(1) angle is 170.9°. As a whole, the molecule has approximate Cs symmetry with the PPh3 ligands

• under the supervision of dedicated staff and all associated safety measures were taken. Parr autoclave was pressure tested at 80 bar before use. Steric interactions of the carbon monoxide coordination to the aryl complex intermediate. A) molecular structure of complex 1; B) ball and stick representation

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• approximately 40–60 nm. Moreover, the PCEs of TTA-DPP4-based devices were higher than those of TTA-DPP2, presumably because of its larger absorption coefficient resulting from its star-shaped molecular structure with a two-dimensionally expanded π-conjugated backbone. Conclusion In this study, the first attempt

• highly different from that of the reported general polymer- and small-molecule-based OSCs. A star-shaped molecular structure containing a two-dimensionally extended π-conjugated system is a promising electronic system for designing photovoltaic organic materials, as a result of its excellent

Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups

• Jakub Saadi,
• Christoph Bentz,
• Kai Redies,
• Dieter Lentz,
• Reinhold Zimmer and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1236–1242, doi:10.3762/bjoc.12.118

• the discovered aryl iodide addition to carbonyl groups may be limited it is attractive since only low catalyst loadings are required and interesting products are formed with high stereoselectivity. Molecular structure (ORTEP, [14]) of compound 12a (thermal ellipsoids at 50% probability). Molecular

• structure (ORTEP, [14]) of compound 14a (thermal ellipsoids at 50% probability). Molecular structure (ORTEP, [14]) of compound 15a (thermal ellipsoids at 50% probability). Molecular structure (ORTEP [14]) of compound 15b (thermal ellipsoids at 50% probability). Planned Heck reaction of A to compound B and

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• confocal Raman microspectroscopy of cells had to wait until laser technology and mathematical image processing have made enough progress [24][25]. In contrast to fluorescence spectroscopy, Raman spectroscopy is label-free, as its scattering effect is unique for a specific molecular structure. Raman spectra

Towards the total synthesis of keramaphidin B

• Pavol Jakubec,
• Alistair J. M. Farley and
• Darren J. Dixon

Beilstein J. Org. Chem. 2016, 12, 1096–1100, doi:10.3762/bjoc.12.104

• murine leukemia cells (IC50 0.28 μg/mL) [1]. It is a member of the manzamine alkaloids and has an exquisite molecular structure comprising a 6,6,6,11,13 pentacycle possessing 4 stereogenic centres including one quaternary centre (Figure 1). In 1992, two years before its isolation, Baldwin and Whitehead

Antibacterial structure–activity relationship studies of several tricyclic sulfur-containing flavonoids

• Lucian G. Bahrin,
• Henning Hopf,
• Peter G. Jones,
• Laura G. Sarbu,
• Cornelia Babii,
• Alina C. Mihai,
• Marius Stefan and
• Lucian M. Birsa

Beilstein J. Org. Chem. 2016, 12, 1065–1071, doi:10.3762/bjoc.12.100

• fluorine atom in their molecular structure. This suggests that the activity against Gram negative bacteria is less dependent on the nature of the introduced heavier halogen (Cl, Br or I). Compound 1 was found to be slightly more potent against S. aureus in terms of bacteriostatic properties than the other

• properties against S. aureus, albeit they were less potent than 1. Moreover, the halogen atoms present in their molecular structure did not greatly influence the MBC values; six out of the seven new flavonoids leading to the same result (exception 5e, Table 5, entry 6). This also applies to the bactericidal

• molecular structure of tricyclic flavonoid 1. The syn and anti-isomers of flavanones 4. Molecular structures of 4d (left) and 4f (right). Ellipsoids represent 50% probability levels [24]. Molecular structure of 5a (left, both independent molecules) and 5b (right, one of two independent molecules

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

• Takashi Nishikata,
• Alexander R. Abela,
• Shenlin Huang and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

• acetonitrile, as confirmed by NMR. The facile formation of this species supports the intermediacy of a palladacycle in the catalytic cycle. The structure of the isolated palladacycle was confirmed by X-ray analysis [216]. An ORTEP plot for palladacycle 6 is shown in Figure 7. The molecular structure consists

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

• Larisa Yu. Gurskaya,
• Diana S. Belyanskaya,
• Dmitry S. Ryabukhin,
• Denis I. Nilov,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 950–956, doi:10.3762/bjoc.12.93

• . Molecular structure of 2f (ellipsoid contours of probability levels are 50%). LUMO of species C1 and D1. Transformations of 3-aryl-N-(aryl)propiolamides 1 into 4-arylquinolin-2(1H)-ones 3 or 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones 2 in the presence of arenes through the formation of intermediate cations A

Separation and identification of indene–C₇₀ bisadduct isomers

• Bolong Zhang,
• Jegadesan Subbiah,
• David J. Jones and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

• electron donor and an electron acceptor) with the film nanostructure being extremely important for the device performance. Molecular structure of IC60BA and IC70BA. a) Schlegel diagram of C70; b) illustrations of three regioisomers of IC70BA and their geometrical isomers. Chromatograms of IC70BA mixture

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• diffusion of diethyl ether into an acetonitrile solution of the copper complex at room temperature. Green-yellow single crystals of complex 2 suitable for an X-ray diffraction study were grown from acetonitrile solution and diethyl ether. The molecular structure of complex 2 in the solid state is depicted

• -ray diffraction study were grown from acetonitrile solution and diethyl ether. The molecular structure of complex 3 is depicted in Figure 2. Complex 3 crystallizes in the monoclinic space group C2/c. The Cu(I) complex contains two crystallographically equivalent Cu centers, which are doubly bridged by

• , which are comparable to the known Cu(I)–NHC complexes [36][37][38][39]. The Cu1–Cu2 separation is 2.7867(7) Å, showing a weak metal−metal interaction. The molecular structure of complex 4 is depicted in Figure 3. Complex 4 consists of the cation unit [Cu2(L3)2]2+ and two hexafluorophosphate anions

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

• Vladislav Vasilenko,
• Torsten Roth,
• Clemens K. Blasius,
• Sebastian N. Intorp,
• Hubert Wadepohl and
• Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 846–853, doi:10.3762/bjoc.12.83

• [2a-PdCl2] and [2a-PdCl]2(BF4)2, and molecular structure of the dimer [2a-PdCl]22+. Anisotropic displacement ellipsoids set at the 50% probability level. Hydrogen atoms have been omitted for clarity. (B) Formation of Pd(allyl) complexes of ligands 2a, 5, and 7. Reaction conditions: (i) DCM, [Pd(cod

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• ]. All bacteria, i.e., Gram-positive and Gram-negative congeners, have a cell wall as part of their cell envelope. While its thickness differs among bacteria – Gram-positive strains usually have a thicker cell wall relative to Gram-negative ones – the principle molecular structure remains identical

Is conformation a fundamental descriptor in QSAR? A case for halogenated anesthetics

• Maria C. Guimarães,
• Mariene H. Duarte,
• Josué M. Silla and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2016, 12, 760–768, doi:10.3762/bjoc.12.76

• conformation of the compounds in a data set is usually unknown and, therefore, geometry optimization is carried out in a receptor-free environment to generate the molecular structure and, subsequently, the 3D MD´s. While molecular conformation in vacuum is governed by intramolecular interactions, the

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• worth mentioning that this equation was used only in the case of TRIMEB and DIMEB CDs, cases in which significant variations were observed concerning the H5 and H3 protons of the CDs. Molecular structure of S4TdR. H atoms are also labeled in the Figure. Comparison between UV–vis absorption spectra

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

• organic materials, I began to see the field of physical organic chemistry more broadly. For my postdoctoral studies, I wanted to learn more about how (macro)molecular structure influences a material’s solution and solid-state properties. I was drawn to Professor Tim Swager’s research based on his

• morphological changes reduced the cgc likely through additional physical entanglements from the longer and/or more prevalent fibers. Combined, these results suggested that additives may be a simple method to modify gel formation without having to alter the molecular structure. We have also explored the more

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• and the coordinating atom bonded to the metal. The two maps are computed with a radius of the sphere equal to 3.5 Å. View of the molecular structure of a) 4H-H and b) 4H-T (main distances in Å). View of the molecular structure of 6. Hydrogen atoms have been omitted for the sake of clarity (main

• ]. The radius of the sphere around the metal centre was set to 3.5 Å, while for the atoms we adopted the Bondi radii scaled by 1.17, and a mesh of 0.1 Å was used to scan the sphere for buried voxels. The steric maps were evaluated with a development version of the SambVca package. View of the molecular

• structure of a) 3H-H and b) 3H-T. Hydrogen atoms have been omitted for the sake of clarity (main distances in Å). Steric maps for the NHC ligand of 3H-H, coordinated to iridium by a) carbene or b) nitrogen. The isocontour curves are given in Å. The systems are oriented along the z-axis defined by the metal

Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

• Norbert Vida,
• Jiří Václavík and
• Petr Beier

Beilstein J. Org. Chem. 2016, 12, 110–116, doi:10.3762/bjoc.12.12

• Norbert Vida Jiri Vaclavik Petr Beier Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic Laboratory of Molecular Structure Characterization, Institute of Microbiology, v.v.i., Academy of Sciences of

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

• Miriana Kfoury,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5

• . Experimental and theoretical results showed that all inclusion complexes have a 1:1 CD:guest stoichiometry and that the molecular structure of the guest affected its binding ability to CD. Kf values determined by an UV–visible competitive method, phase solubilty studies and 1H and DOSY 1H NMR titration

Friedel–Crafts-type reaction of pyrene with diethyl 1-(isothiocyanato)alkylphosphonates. Efficient synthesis of highly fluorescent diethyl 1-(pyrene-1-carboxamido)alkylphosphonates and 1-(pyrene-1-carboxamido)methylphosphonic acid

• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Anna Gajda,
• Tadeusz Gajda,
• Anna Makal,
• Arnaud Brosseau and
• Rémi Métivier

Beilstein J. Org. Chem. 2015, 11, 2451–2458, doi:10.3762/bjoc.11.266

• an X-ray diffraction study (vide infra). Molecular structure, crystal packing and solid-state fluorescence of 3a Compound 3a crystallized from layered dichloromethane–hexane in the monoclinic space group P21/c, with a single molecule occupying an asymmetric unit in general position. Its molecular

• 3a in CHCl3 (c = 10−6 M) and its solid-state emission spectrum (yellow). λexcit = 360 nm. Molecular structure of 3a (ORTEP representation). Displacement ellipsoids were drawn at a 50% probability level. Hydrogen atom labels are analogous to those of bonded non-H atoms and were omitted for clarity

• structure is shown in Figure 6. The pyrenyl moiety in 3a is slightly bent, the angle between the planes of rings C1–C2–C15–C14–C13–C12 and C5–C6–C7–C8–C9–C16 is 4.23(13)°. The amide group is twisted by 57.1(2) degrees from the plane of the C1–C2–C15–C14–C13–C12 ring. Together with the C1–C17 bond length

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

• units and urethane groups (Figure 1). The combination of the urethane group (forming hydrogen bonds) and the TTF unit (forming π–π stacking) may promote the formation of nanostructures. To the best of our knowledge, urethane groups have been rarely introduced into the molecular structure of TTF

• /iodine resulted in the formation of charge transfer states exhibiting semiconducting properties. There is significant potential for the application of the conducting nanoribbons in molecular electronics devices. Molecular structure of TTF derivatives T1 and T2. SEM images of T1 (a) and T2 (b) films on

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

• Yury A. Sayapin,
• Inna O. Tupaeva,
• Alexandra A. Kolodina,
• Eugeny A. Gusakov,
• Vitaly N. Komissarov,
• Igor V. Dorogan,
• Nadezhda I. Makarova,
• Anatoly V. Metelitsa,
• Valery V. Tkachev,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

• (4,5,6,7-tetrachloro)-1,3-tropolones with alcohols leads to the contraction of the seven-membered tropone ring with the formation of 2-(2-benzoxa(thia)zolyl)-6-alkoxycarbonylphenols. The molecular structure of 2-(2-ethoxycarbonyl-6-hydroxy-3,4,5-trichlorophenyl)benzoxazole has been determined by X-ray

• reaction. A tentative mechanism for the reaction is proposed in Scheme 5. The molecular structure of the obtained 2-(3,3-dimethylindolyl)-1,3-tropolone 13 is shown in Figure 3. As is the case of other studied 2-hetaryl-1,3-tropolones, compound 13 exists in the (NH) ground state tautomeric form with a very

• strong intramolecular N–H···O hydrogen bond that closes up the cycle Н(1)–N(1)–С(8)–С(2)–С(3)–О(2). The N(1)···О(2) distance (2.514 Å) is 0.5 Å shorter than the corresponding van der Waals contact angle. The molecular structure of a representative 2-(2-ethoxycarbonyl-6-hydroxy-3,4,5-trichlorophenyl

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

• Mingxing Liu,
• Jiarong Li,
• Hongxin Chai,
• Kai Zhang,
• Deli Yang,
• Qi Zhang and
• Daxin Shi

Beilstein J. Org. Chem. 2015, 11, 2125–2131, doi:10.3762/bjoc.11.229

• the detailed mechanism and synthetic application of this protocol are in progress. Four-component one-pot synthesis of 5. Reactions conditions: 1 (1.2 mmol), 2 (1.0 mmol), 3 (1.2 mmol) and 4 (1.2 mmol) in alcohol (15 mL). Molecular structure (from X-ray diffraction data) of 5g. The synthesis of