Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• featuring monodentate [44][45], chelating bidentate [46][47][48][49][50][51][52][53][54][55], or bridging bidentate NHC·CS2 ligands [45][51][52]. Small bimetallic clusters [51][52][56], coordination polymers [57], self-assembled monolayers [58], and nanoparticles [45] based on these zwitterions were also

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

• Kendra Drayton-White,
• Siyue Liu,
• Yu-Chia Chang,
• Sakashi Uppal and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

• interactions can be minimized for a variety of biological targets. Self-assembled monolayers do not have this stability, and strategies that chemically modify carbon electrodes do not offer the chemical flexibility or surface tunability needed. Hence, an alternative strategy is required. This led to the

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• , solvent choice [81], and application of self-assembled monolayers (SAM). SAMs are coated on the dielectric medium, improving surface roughness [82] and reduce interfacial defects [83]. Details about device fabrication are described in Supporting Information File 1. Device optimisation was necessary since

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• mobility [20], but no control over the crystal size and morphology was demonstrated. Using self-assembled monolayers as templates for the seeding and growth of molecular crystals may offer control over structure and polymorphism [21]. However, in this method, the crystal formation is limited by the

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• immobilized receptors exist. Solutions of AuNPs containing tetracationic resorcinarene-derived cavitands were, for example, also shown to respond to the presence of diphosphate by a color change [27] due to the known diphosphate affinity of such cavitands [28]. Self-assembled monolayers on gold containing a

Nanopatterns of arylene–alkynylene squares on graphite: self-sorting and intercalation

• Tristan J. Keller,
• Joshua Bahr,
• Kristin Gratzfeld,
• Nina Schönfelder,
• Marcin A. Majewski,
• Marcin Stępień,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2019, 15, 1848–1855, doi:10.3762/bjoc.15.180

• and non-planar coronoid polycyclic aromatic hydrocarbons (i.e., butyloxy-substituted kekulene and octulene derivatives) are found to be able to intercalate into the intramolecular nanopores. Keywords: macrocycles; scanning tunneling microscopy; self-assembled monolayers; self-sorting; solid/liquid

• solvent molecules are sometimes resolved as intercalation adducts in STM of self-assembled monolayers. On the other hand, reports on intercalated TCB molecules are rather rare. Two exceptions are the observations of TCB in monolayers of arylene–alkynylene pentagons as well as triphenylene/azobenzene-based

• ]. At the solid/liquid interface of solutions of 2 in a concentration range of 10−3 M to 10−5 M in TCB on HOPG, self-assembled monolayers of 2 are found (see Supporting Information File 1). We studied whether 2 can adsorb into the nanopores formed by 1a. Therefore, first a nanopattern of 1a was (self

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

• ; quadricyclane; self-assembled monolayers; TATA platform; thermal isomerization; TOTA platform; Introduction Recently, we discovered that the thermochemically forbidden cis–trans isomerization of azobenzenes can be efficiently catalysed by a very peculiar mechanism on bulk gold [1]. In heterogeneous catalysis

• bridge atom of the TATA platform in QC 1b at time t, [QC]0 corresponding 1H integral at t = 0. A rate constant of k = 0.95·10−3 s−1 was determined from a linear fit of the ΔY/t curve. (a) STM image of self-assembled monolayers of compound 1 on Au(111) (40 × 40 nm2, It = 0.05 nA, Ubias = 0.40 V) and (b

Diazocine-functionalized TATA platforms

• Roland Löw,
• Talina Rusch,
• Fynn Röhricht,
• Olaf Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1485–1490, doi:10.3762/bjoc.15.150

• ordered monolayers on Au(111) surfaces. Keywords: cis–trans isomerization; diazocine; molecular switch; photochrome; self-assembled monolayers; TATA platform; Introduction Catalysts increase chemical reaction rates by lowering the activation energies and thus create more favorable reaction pathways [1

• self-assembled monolayers of (a) compound 1 and (b) compound 2 on Au(111). Synthesis route of para-diazocine platform molecule 1. a) Pd(dppf)Cl2, Cu(I)I, Et3N, 1 h, 60 °C; b) 1: KOt-Bu, THF, 3 min, 0 °C, N2; 2: Br2, 5 min, 0 °C; c) 1: Ba(OH)2, Zn, EtOH, H2O, 4.75 h, reflux; 2: 0.1 M NaOH/MeOH, Cu(II

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

• Leon Buschbeck,
• Aleksandra Markovic,
• Gunther Wittstock and
• Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

• (absorption at 514 nm, emission at 566 nm). The quantum yield is, however, lower (4%). Self-assembled monolayers on a gold surface of both compounds were prepared and characterized by high-resolution XPS of the C 1s, O 1s, S 2p, N 1s and F 1s emissions. The high signal-to-noise ratios of the F 1s peaks

• indicated that trifluoromethylation is an excellent tool for the detection of surface-bound materials by XPS. Keywords: chromophore; diaminoterephthalate; fluorine surface marker; fluorescence dye; lipoic acid; self-assembled monolayers; Introduction Diaminoterephthalates (DATs) are powerful fluorescence

• emission and absorption wavelengths in solution (CH2Cl2) of compound 7 were bathochromically shifted (λmax = 514 nm, λem = 566 nm). However, the quantum yield of 7 was on the other hand significantly lower (Φ = 4%). Self-assembled monolayers (SAMs) of both compound 3 and 7 were prepared on a gold surface

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

• Tilman Lechel,
• Roopender Kumar,
• Mrinal K. Bera,
• Reinhold Zimmer and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

• this experiment was the double-coupling product OX27 and the mono-coupling product (not shown) was isolated in 5% yield [45]. A solution of the C3-symmetric compound OX28 in 1-phenyloctane was investigated by scanning tunneling microscopy (STM) to reveal its ability to form self-assembled monolayers at

Steric “attraction”: not by dispersion alone

• Ganna Gryn’ova and
• Clémence Corminboeuf

Beilstein J. Org. Chem. 2018, 14, 1482–1490, doi:10.3762/bjoc.14.125

• alkanes [71], fail to accurately reproduce the chain length dependence of the tilt and twist angles in alkanethiol self-assembled monolayers [72] and increasingly deviate (by as much as 15%) from experimental data for the hydrophobic solvation free energies of alkanes in alkanes with the increasing chain

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

• Vivek Poonthiyil,
• Thisbe K. Lindhorst,
• Vladimir B. Golovko and
• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

• multivalent carbohydrate structures led to the development of self-assembled monolayers (SAMs) of carbohydrates on the spherical surface of AuNPs. In 2001, the Penadés group reported the first synthesis of AuNPs with attached carbohydrates [8]. These systems, termed ‘glyco-gold nanoparticles’ (GAuNPs), were

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• that were used for self-assembled monolayers (e.g., compound 61 [187]), polymers (PEG derivative 62 [188] or functionalized polyethylene 63 [189]) were reported. The McKenna’s procedure was also applied to prepare polyphosphonic acids as exemplified by the compounds 64 [120], 65 [190], 66 [191] and the

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

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• Surface, UMR CNRS 7197, 4 place Jussieu, 75005 Paris, France Université de Nantes, CNRS, CEISAM, UMR 6230, Faculté des Sciences et des Techniques, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France 10.3762/bjoc.13.64 Abstract Aniline-terminated self-assembled monolayers (SAMs) on gold surfaces

• contact angle (WCA) measurements, Fourier-transform infrared reflection absorption spectroscopy (IRRAS) and X-ray photoelectron spectroscopy (XPS). Keywords: gold surfaces; hydrolysis; IRRAS; reversibility; SAM; sulfamide; XPS; Introduction Self-assembled monolayers (SAMs) have raised considerable

• for the formation of aromatic mixed self-assembled monolayers containing both imine functionalities and protonated anilines on the surface [20]. In order to bring a new class of reusable surfaces, we describe herein the use of sulfamide chemistry for the generation of reversible patterns of sulfur

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• to form self-assembled monolayers on gold [69][70][71] as well as on zinc and iron oxide surfaces [72]. Conceptually, thienyl-bridged oligophenothiazines can be considered as a novel type of structurally well-defined electron-rich oligophenothiazine–thiophene hybrids (Figure 1). Thereby, the strong

Optimized methods for preparation of 6^I-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives

• Eva Bednářová,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2016, 12, 349–352, doi:10.3762/bjoc.12.38

• -cyclodextrins (β-CD-S-X-SH) – which can be attached to a gold surface [9][10] or a polydopamine-coated surface [11]. It has been already described that the surface coverage of self-assembled monolayers of CD derivatives on gold depends substantially on the linker between the sulfanyl group and the CD

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• transistors (OFETs) Compounds 1 and 2 were used in the fabrication of bottom-gate bottom-contact OFETs to give an indication on the applicability of these small molecules to organic semiconductor devices. The use of self-assembled monolayers (SAMs) was investigated with pentafluorobenzenethiol (PFBT) and

• solutions in dichloromethane. Optimised structures of 1 (left), 2 (centre) and 3 (right). Output characteristics of OFETs fabricated using compound 2 in CHCl3 with OTS (top) and PFBT/OTS (bottom) as self-assembled monolayers. AFM images of OFET devices fabricated using compound 2 in CHCl3 with OTS (left

Single-molecule conductance of a chemically modified, π-extended tetrathiafulvalene and its charge-transfer complex with F₄TCNQ

• Raúl García,
• M. Ángeles Herranz,
• Edmund Leary,
• M. Teresa González,
• Gabino Rubio Bollinger,
• Marius Bürkle,
• Linda A. Zotti,
• Yoshihiro Asai,
• Fabian Pauly,
• Juan Carlos Cuevas,
• Nicolás Agraït and
• Nazario Martín

Beilstein J. Org. Chem. 2015, 11, 1068–1078, doi:10.3762/bjoc.11.120

• ]. It is also rational to suppose that the, albeit charged, dithiole side groups of our CT complex would not strongly modify the conductance of the otherwise neutral anthracene-containing wire. Finally, we point out that recent conductive AFM measurements carried out on self-assembled monolayers of

Electrochemical oxidation of cholesterol

• Jacek W. Morzycki and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

• ]. An interesting technique for non-enzymatic sensors represents molecularly imprinted self-assembled monolayers. In this approach, the layer containing organic compounds together with cholesterol is deposited on an electrode surface. Then, the cholesterol is removed from the layer, and the oxidation

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• ][17][18]. This approach offers self-assembled monolayers (SAMs) which can be utilized for derivatization of gold electrodes for the construction of electrochemical sensors [19][20] or even for the development of molecular printboards [21]. These results imply that the structure of CD derivatives

Organic chemistry on surfaces: Direct cyclopropanation by dihalocarbene addition to vinyl terminated self-assembled monolayers (SAMs)

• Malgorzata Adamkiewicz,
• David O’Hagan and
• Georg Hähner

Beilstein J. Org. Chem. 2014, 10, 2897–2902, doi:10.3762/bjoc.10.307

• Malgorzata Adamkiewicz David O'Hagan Georg Hahner EaStCHEM School of Chemistry, University of St. Andrews, St. Andrews, Fife KY16 9ST, UK 10.3762/bjoc.10.307 Abstract C11-Vinyl-terminated self-assembled monolayers (SAMs) on silica surfaces are successfully modified in C–C bond forming reactions

• with dihalocarbenes to generate SAMs, terminated with dihalo- (fluoro, chloro, bromo) cyclopropane motifs with about 30% surface coverage. Keywords: difluoro-; dichloro-; dibromomethylenecyclopropanes; dihalocarbenes; self-assembled monolayers; surface coating; Introduction Self-assembled monolayers

• incorporating functional groups (FGs) on the surface of self-assembled monolayers (SAMs), illustrated for alkylsilanes onto silica. XPS scans after reactions with a) :CBr2; b) :CCl2 and c) :CF2. In each case the upper traces are scans of C11-vinyl SAMs, and the lower traces are C18-Me-terminated SAMs each

Mono- and multilayers of molecular spoked carbazole wheels on graphite

• Stefan-S. Jester,
• A. Vikas Aggarwal,
• Daniel Kalle and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 2783–2788, doi:10.3762/bjoc.10.295

• Stefan-S. Jester A. Vikas Aggarwal Daniel Kalle Sigurd Hoger Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany 10.3762/bjoc.10.295 Abstract Self-assembled monolayers of a molecular spoked wheel (a shape

• the second layer. Keywords: molecular spoked wheels; scanning tunneling microscopy; self-assembled monolayers; solid/liquid interface; template; Introduction Molecular spoked wheels (MSWs) have gained increasing interest as two-dimensional (2D) carbon-based objects of adjustable sizes [1][2][3][4][5

Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

• Joscha Vollmeyer,
• Friederike Eberhagen,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2014, 10, 2774–2782, doi:10.3762/bjoc.10.294

• macrocycle distances are mainly determined by their size and symmetry. This is an excellent example that the graphite acts as a template for the macrocycle organization independent from their specific interior. Keywords: conformational polymorphism; self-assembled monolayers; shape-persistent macrocycles

Theoretical study of the adsorption of benzene on coinage metals

• Werner Reckien,
• Melanie Eggers and
• Thomas Bredow

Beilstein J. Org. Chem. 2014, 10, 1775–1784, doi:10.3762/bjoc.10.185

• ; dispersion correction; template; Introduction The adsorption of organic molecules on metals is of great interest since the formation of thin films and self-assembled monolayers opens the way toward a functionalization of surfaces [1][2][3][4][5][6][7][8]. The adsorbed molecules often contain an aromatic