Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• class of small molecules that can form reversible supramolecular gels in organic solvents or aqueous solutions [1][2][3][4][5][6][7][8][9]. Non-covalent interactions such as hydrogen bonding, hydrophobic interactions, and π–π stacking are the main driving forces for the self-assembly of the gelators

Self-assembly and semiconductivity of an oligothiophene supergelator

• Pampa Pratihar,
• Suhrit Ghosh,
• Vladimir Stepanenko,
• Sameer Patwardhan,
• Ferdinand C. Grozema,
• Laurens D. A. Siebbeles and
• Frank Würthner

Beilstein J. Org. Chem. 2010, 6, 1070–1078, doi:10.3762/bjoc.6.122

• -type aggregate to monomeric building blocks at elevated temperature. The self-assembly of T1 at such low concentrations can be attributed to the synergistic effect of π-π-stacking among the oligothiophene chromophores and intermolecular hydrogen bonding between the amide groups of the neighbouring

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• motif for materials applications. For example, benzyl and thienyl annelated TTF derivatives and analogues have been shown to perform well as semiconductor materials in organic field effect transistors (OFETs) [21][22]. This has been attributed to the enhanced π–π stacking of the extended aromatic groups

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

• properties were related to hydrogen bonding, hydrophobic interactions and π-π stacking. Herein, β-Ala-His-EO2-Alk was fully characterised by FT-IR, NMR, SAXS and SEM and the gelation mechanism is discussed. It appears that the number of amide groups determines the self-assembling behaviour into 1D or 2D/3D

• as electrostatic, hydrogen bonding, dipole–dipole, π–π stacking and hydrophobic/van der Waals interactions. Since the cross-links between fibres are non-covalent in nature, LMWHs exhibit thermoreversibility, rapid response to external stimuli (i.e., stirring, sonication). Among these LMWHs, amino

• hydrophilic and hydrophobic modules, as well as the number of H-donor and H-acceptor centers, or π–π stacking. Therefore the appropriate balance between all these factors must be determined. As a part of the ongoing research carried out in our laboratory on the self-assembled systems of amino acids-based

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• hydrophobic interactions is mandatory for any gelation process. Non-covalent interactions such as hydrogen bonding, ionic interactions, π–π stacking or van der Waals forces play a pivotal role in self-assembled gelation [12]. Tuning the structure of gelator molecules leads to a better understanding of the

• gelation. The planar aromatic moiety favors π–π stacking interactions between the molecules and leads to the formation of 3D networks of viscoelastic gels [25][26][27]. Interestingly, among all these aromatic rings, the positively charged pyridine (pyridinium) unit is well known to impart antibacterial

• pyridinium moieties in order to exploit its favorable π–π stacking interaction towards self-assembled gelation as well as an ability to kill bacteria. Furthermore, a very simple method of synthesizing such amphiphilic antibacterial hydrogelators with pyridinium units would definitely boost its importance and

Chiral gels derived from secondary ammonium salts of (1R,3S)-(+)-camphoric acid

• Tapas Kumar Adalder,
• N. N. Adarsh,
• Ravish Sankolli and
• Parthasarathi Dastidar

Beilstein J. Org. Chem. 2010, 6, 848–858, doi:10.3762/bjoc.6.100

• can be of two kinds – chemical or polymeric and physical or supramolecular. While covalent bonds are responsible for the formation of 3-D networks in chemical gels, various non-covalent interactions such as hydrogen bonding, π-π stacking, hydrophobic, van der Waals forces etc. are required to form gel

• sustained by weak π-π stacking interactions (3.926 Å) involving the phenyl groups of the neighboring 2-D sheets (Figure 6). Crystals of DCHADC 1 was grown from m-xylene. It was crystallized in the non-centrosymmetric monoclinic space group P21. The C–O distance of the carboxylic acid moieties are 1.226(10

Organic gelators and hydrogelators

• Jean-Pierre Desvergne

Beilstein J. Org. Chem. 2010, 6, 846–847, doi:10.3762/bjoc.6.99

• liquid) which behaves as a visco-elastic material (soft matter) due to the immobilization of solvent molecules in a three-dimensional network. This network results from the self-assembly of the gelling agent into fibres via non-covalent interactions such as hydrogen bonding, π–π stacking, van der Waals

En route to photoaffinity labeling of the bacterial lectin FimH

• Thisbe K. Lindhorst,
• Michaela Märten,
• Andreas Fuchs and
• Stefan D. Knight

Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91

• residues Tyr48 and Tyr137 (‘tyrosine gate’) that can form favorable interactions with appropriate mannosidic aglycone moieties, such as π-π-stacking with the phenyl group of benzyl mannosides [14]. In a preceding work, we synthesized the three corresponding photoactive α-D-mannosides, 1, 2, and 3 (Figure

Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones

• Kerstin Schmidt and
• Paul Margaretha

Beilstein J. Org. Chem. 2010, 6, No. 76, doi:10.3762/bjoc.6.76

• compounds tend to associate via π–π-stacking, and b) radical additions to alkynes usually proceed with significantly lower relative rates (30–50%) than those to the corresponding alkenes [7]. Taking these findings and the observed regioselectivity of the cycloaddition into consideration, the maximum

9,10-Dioxa-1,2-diaza-anthracene derivatives from tetrafluoropyridazine

• Graham Pattison,
• Graham Sandford,
• Dmitrii S. Yufit,
• Judith A. K. Howard,
• John A. Christopher and
• David D. Miller

Beilstein J. Org. Chem. 2010, 6, No. 45, doi:10.3762/bjoc.6.45

• , parallel to the [101] direction and π···π stacking interactions (shortest interatomic distance C5···C3 is 3.336 Å), and short C–H···O contacts (C···O 3.387 Å) bind adjacent chains in the [100] and [010] directions, respectively. Again, the regiospecificity of these reaction processes occurs because of the

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

• enantiomeric discrimination (Table 4): With preference for the R-enantiomers, the benzo- and naphtho-18-crown-6 33a and 33b generally revealed a larger flux of the aromatic amino acids or their salts than hosts 32a and 32b [164]. This was attributed to a strong π–π stacking interaction. The highest flux values

Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2010, 6, No. 14, doi:10.3762/bjoc.6.14

• of guest from secondary dibenzylammonium hexafluorophosphate (360 M−1, 1.0 mM, in acetone-d6) [31] to the anthracenyl methyl-substituted analogue 5-H•PF6 (496 M−1, 1.0 mM, in acetone-d6) [26] increases the binding affinity with DB24C8, which is mainly attributed to stronger π-π stacking interactions

• reasons for this remarkable difference between C7 and the larger analogue dibenzo-24-crown-8. (i) According to related crystal structures [23][24][25], no π-π stacking interactions operate between hosts C7 or 4 and guests 6-H•PF6 or 7-H•PF6. (ii) Even more important, however, are the polarized methylene

Crystal engineering of analogous and homologous organic compounds: hydrogen bonding patterns in trimethoprim hydrogen phthalate and trimethoprim hydrogen adipate

• Packianathan Thomas Muthiah,
• Savarimuthu Francis,
• Urszula Rychlewska and
• Beata Warżajtis

Beilstein J. Org. Chem. 2006, 2, No. 8, doi:10.1186/1860-5397-2-8

• leading to base-pairing, quadruple hydrogen bonded arrays, DDAA and DADA (D- donor, A = acceptor), etc. C-H...π, π-π stacking, etc are further stabilizing the crystal structures. The quadruple hydrogen bonded arrays have been observed in the crystal structures of TMP m-chlorobenzoate, [11] TMP-sorbate