Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• section we will discuss the utility of some of the well-established catalytic nanoreactors towards green(er) chemistry [62]. 2.1. Micelles Micelles are supramolecular architectures that are assembled of amphiphilic molecules [41]. Above the critical micellar concentration (CMC), surfactants with the

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

• -tetraazaadamantane derivative was demonstrated. Keywords: azoalkenes; α-halogen hydrazones; heterocage compounds; hydrazone ligands; Michael addition; Introduction Hydrazones are extensively used as key structural units in the design of various functional molecular and supramolecular architectures [1][2][3][4][5

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

• : azulene; fluorescence; metal binding; synthesis; terpyridine; Introduction 2,2′:6′,2″-Terpyridine derivatives are extensively used organic ligands in the field of supramolecular chemistry and materials science [1][2][3][4]. Besides the interesting supramolecular architectures, metal–terpyridine complexes

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• a wide range of molecular and supramolecular architectures derived from the simple glycoluril motif [28]. Another early molecular tweezer developed by Harmata was notable because of its chirality. Harmata and his undergraduate student, Tom Murray (who later obtained his Ph.D. in my group), showed

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• wide variety of host molecules have the ability to encapsulate the π-conjugated backbones into their cavities based on intermolecular interactions, and thus leading to ICs. Cyclodextrins (CDs) are by far the most intensively investigated macrocyclic molecules in the synthesis of such supramolecular

• architectures [39]. The second most investigated group of host molecules in the synthesis of conjugated polyrotaxanes is comprised of chemically-modified CDs. They are less hydrophilic than native CDs, and should exhibit a significantly increased ability to bind aromatic guests through ionic, ion-dipole, as

Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

• Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

• environments [46]. The high stability of the folded conformation of the 22 series also make them useful frameworks for creating a variety of complicated supramolecular architectures [42]. Although alkoxyl groups had been popularly used as acceptors for intramolecular hydrogen bonding [40][41][42], I was also

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• functional dyes [22][23]. Furthermore, various multifunctional TTF-based supramolecular architectures have been designed and synthesized to realize molecular sensors, redox switches, multi-input systems for logic gates, electrochemically-driven conformational controls, molecular clips and tweezers, and redox

Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths

• Yuchun Ren,
• Bin Wang and
• Xiuqing Zhang

Beilstein J. Org. Chem. 2015, 11, 1089–1095, doi:10.3762/bjoc.11.122

• new classes of organogelator architectures have been systematically studied because of their reversible gel process and unique directional self-association through weak van der Waals interactions [16][17]. Up to now, numerous attempts have been made to develop novel supramolecular architectures, which

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• ]+˙ mixed-valence dimer and/or (TTF+˙)2 dimer species concerned systems for which the dimer stabilization is resulting from the close proximity of the two TTF units. That is the case for conjugated bisTTF systems [51], bisTTF-substituted calix[4]arenes [52], or supramolecular architectures such as [3

Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

• Mirko Lohse,
• Larissa K. S. von Krbek,
• Sebastian Radunz,
• Suresh Moorthy,
• Christoph A. Schalley and
• Stefan Hecht

Beilstein J. Org. Chem. 2015, 11, 748–762, doi:10.3762/bjoc.11.85

• structures, functional supramolecular architectures such as molecular switches and motors [43][44][45] as well as artificial muscles [46][47][48][49][50], have been synthesized. Due to their four-fold symmetry, porphyrins are excellent candidates to extend these concepts to tetravalent supramolecules. Beyond

• to exploit the concept of complementary multivalent binding to program the increasingly complex self-assembly of multiple different chromophore components into functional supramolecular architectures. Mono-, di-, and tetravalent axles A1, A2 and A4 and mono-, di-, and tetravalent hosts C1, C2 and C4

Self-assembly of heteroleptic dinuclear metallosupramolecular kites from multivalent ligands via social self-sorting

• Christian Benkhäuser and
• Arne Lützen

Beilstein J. Org. Chem. 2015, 11, 693–700, doi:10.3762/bjoc.11.79

• attractive since they allow access to much more complex supramolecular architectures than homoleptic systems do. Unfortunately, the selective formation of heteroleptic complexes from a mixture of different multivalent ligands bridging two or more metal ions is more challenging and there is only a limited

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• 7, 14183, Huddinge, Sweden 10.3762/bjoc.10.154 Abstract Pyrene derivatives can be incorporated into nucleic acid analogs in order to obtain switchable probes or supramolecular architectures. In this paper, peptide nucleic acids (PNAs) containing 1 to 3 1-pyreneacetic acid units (PNA1–6) with a

Creating Complexity

• Donald Craig

Beilstein J. Org. Chem. 2013, 9, 1881–1882, doi:10.3762/bjoc.9.220

• synthesis chemists are engaged in the creation of novel polymeric materials with a wide range of applications, the conception and fabrication of new supramolecular architectures, and in the exploration of new regions of chemical space in the contexts of drug discovery and development. As synthesis nears its

Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach

• Sandeep Kumar,
• Ramendra Pratap,
• Abhinav Kumar,
• Brijesh Kumar,
• Vishnu K. Tandon and
• Vishnu Ji Ram

Beilstein J. Org. Chem. 2013, 9, 809–817, doi:10.3762/bjoc.9.92

• of the weak noncovalent interactions operating in the supramolecular architectures of alkenylated indoline-2-ones and to explain the relative stability of one of the tautomers with respect to the others. Keywords: alkenylation; dibenzo[d,f][1,3]diazepin-6(7H)-one; indolin-2-one; ketene dithioacetal

Low-generation dendrimers with a calixarene core and based on a chiral C₂-symmetric pyrrolidine as iminosugar mimics

• Marco Marradi,
• Stefano Cicchi,
• Francesco Sansone,
• Alessandro Casnati and
• Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

• [38][39], which are objects of current investigations. Conclusion The coupling of low-generation dendrons, based on the chiral C2-symmetric dihydroxypyrrolidine 1, with a calix[4]arene scaffold allowed the construction of novel supramolecular architectures, i.e., iminosugar-analogue-based calixarene

Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions

• Yagang Zhang and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2012, 8, 486–495, doi:10.3762/bjoc.8.55

• of lower molecular weight. The utility of these units is further demonstrated in the broad range of supramolecular architectures that have emerged and the materials to which these units have been attached, including dendrimers [15][16][17], polymer chain-ends [18][19][20] and polymer side-chains [21

A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction

• Christian Eidamshaus,
• Roopender Kumar,
• Mrinal K. Bera and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2011, 7, 962–975, doi:10.3762/bjoc.7.108

• metal-catalyzed processes and for the construction of supramolecular architectures [13]. Pyridines with chiral side chains are widely employed as ligands in asymmetric transformations, for instance, in the asymmetric hydrogenation of olefins, in enantioselective additions of metal organyls to aldehydes

Anion–π interactions influence pK_a values

• Christopher J. Cadman and
• Anna K. Croft

Beilstein J. Org. Chem. 2011, 7, 320–328, doi:10.3762/bjoc.7.42

• interactions could be used in supramolecular architectures to modulate reactivity. Likewise, interactions of this type may play a guiding role in some enzyme reactions. Experimental General The 1H and 13C NMR spectra were recorded on a Bruker Avance 500 Digital NMR spectrometer at 500 MHz in CDCl3. GC-MS

Differences between β-Ala and Gly-Gly in the design of amino acids-based hydrogels

• Andreea Pasc,
• Firmin Obounou Akong,
• Sedat Cosgun and
• Christine Gérardin

Beilstein J. Org. Chem. 2010, 6, 973–977, doi:10.3762/bjoc.6.109

• building blocks for supramolecular architectures such as gels [8][9]. The structure of the surfactant is a major factor for their gelator properties. As reported in the literature [1], unless the molecules remain in solution, when a hot, homogeneous solution of the gelator, is cooled, the molecules start

Towards racemizable chiral organogelators

• Jian Bin Lin,
• Debarshi Dasgupta,
• Seda Cantekin and
• Albertus P. H. J. Schenning

Beilstein J. Org. Chem. 2010, 6, 960–965, doi:10.3762/bjoc.6.107

• ; organogels; racemization; self-assembly; Introduction Gelation represents a macroscopic manifestation of self-assembled molecules. Impressive supramolecular architectures have been reported in which the self-assembled molecules immobilize solvent to produce a gel phase. Carefully designed self complementary

Chain stopper engineering for hydrogen bonded supramolecular polymers

• Thomas Pinault,
• Bruno Andrioletti and
• Laurent Bouteiller

Beilstein J. Org. Chem. 2010, 6, 869–875, doi:10.3762/bjoc.6.102

• ureas and thioureas and tested them as chain stoppers for a bis-urea based supramolecular polymer. Depending on the solvent used, the bis-urea either forms filaments with a single monomer in the cross-section or tubes with three monomers in the cross-section. For both supramolecular architectures

Calix[4]arene-click-cyclodextrin and supramolecular structures with watersoluble NIPAAM-copolymers bearing adamantyl units: “Rings on ring on chain”

• Bernd Garska,
• Monir Tabatabai and
• Helmut Ritter

Beilstein J. Org. Chem. 2010, 6, 784–788, doi:10.3762/bjoc.6.83

• superstructures, CDs and calixarenes turned out to be very attractive not only as molecular receptors but also as building blocks for the construction of supramolecular architectures [5]. For that reason, we were encouraged to couple these two different types of macrocycles via click type reactions. Recent

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

• Magnus Rueping and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

• “exhaustive” Pd(0)-catalyzed allylation of benzene-1,3,5-triol (67), resulting in the highly allylated cyclohexane-1,3,5-trione 69 in high yields. This structure is expected to be a useful precursor for supramolecular architectures with C3 symmetry (Scheme 28) [81]. It is worth mentioning that in this example

The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts

• Kari Raatikainen,
• Massimo Cametti and
• Kari Rissanen

Beilstein J. Org. Chem. 2010, 6, No. 4, doi:10.3762/bjoc.6.4

• halopyridinium salt structures which clearly show how the balance of intermolecular interactions such as HB and XB can determine the supramolecular architectures found in the solid state (Scheme 1). The detailed study of the seven new crystal structures, namely anilinium salts 4-IPhNH3Cl (1), 4-IPhNH3Br (5), 4

• confirmed by the halopyridinium salts 9–13 which clearly represented the strongest halogen bonding in the studied series. While N-benzyl-3-iodopyridinium chloride (9) can be considered as a reference system where only halogen bonded existed, structures 10–13 manifested supramolecular architectures where