Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• that the formation of a gel structure was observed for concentrations as low as 0.5 wt %. Organogelators that are able to gel solvents at concentrations at <1% are classified as supergelators [29][30][31]. Furthermore, the results from the solubility tests where the ability of gelation decreases with

Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

• Juan V. Alegre-Requena,
• Marleen Häring,
• Isaac G. Sonsona,
• Alex Abramov,
• Eugenia Marqués-López,
• Raquel P. Herrera and
• David Díaz Díaz

Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

• describe the preparation and characterization of two new unsymmetrical squaramide-based organogelators. The synthesis of the compounds was carried out by subsequent amine condensations starting from dimethyl squarate. The design of the gelators involved a squaramide core connected on one side to a long

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• class of organogelators based on triphenylmethyl derivatives of simple and easily available primary alcohols. One big advantage of these gelators is their straightforward synthesis and easy accessibility. Overall, gelation efficiency of some of the triphenylmethyl derivatives was moderate to excellent

• structures of triphenylmethyl-based organogelators. Gelation properties of TPM-G1 – TPM-G15a,b. Supporting Information Supporting Information File 58: Experimental part. Acknowledgements W.P.S gratefully acknowledges UGC, India for providing a Non-NET fellowship. This work was partially supported by the

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

• organogelators and soft matter. Changes in the absorption over time in the UV–vis spectra of dilute THF solution of M0: (a) upon UV-light irradiation (λ = 365 nm) and (b) upon visible-light irradiation (λ = 450 nm) of the solution obtained after irradiation of 365 nm. DSC thermogram of the compounds M0-n

Improving the reactivity of phenylacetylene macrocycles toward topochemical polymerization by side chains modification

• Simon Rondeau-Gagné,
• Jules Roméo Néabo,
• Maxime Daigle,
• Katy Cantin and
• Jean-François Morin

Beilstein J. Org. Chem. 2014, 10, 1613–1619, doi:10.3762/bjoc.10.167

• -assembly of two new phenylacetylene macrocycle (PAM) organogelators were performed. Polar 2-hydroxyethoxy side chains were incorporated in the inner part of the macrocycles to modify the assembly mode in the gel state. With this modification, it was possible to increase the reactivity of the macrocycles in

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

• Pablo Morán-Poladura,
• Eduardo Rubio and
• José M. González

Beilstein J. Org. Chem. 2013, 9, 2120–2128, doi:10.3762/bjoc.9.249

• for functional applications. Thus, for instance, this molecular frame has been associated with photochromic crystals [7], photochromic organogelators [8], selective cyclooxygenase-2 inhibitors [9][10], antifungal [11] and antitrypanocidal activity [12], transforming growth factor-β receptors [13] and

Self-assembly of 2,3-dihydroxycholestane steroids into supramolecular organogels as a soft template for the in-situ generation of silicate nanomaterials

• Valeria C. Edelsztein,
• Andrea S. Mac Cormack,
• Matías Ciarlantini and
• Pablo H. Di Chenna

Beilstein J. Org. Chem. 2013, 9, 1826–1836, doi:10.3762/bjoc.9.213

• between the anionic silicate intermediate species and the self-assembled fibrillar network. Keywords: Hansen parameters; nanotube; organogel; self-assembly; supramolecular gel; Introduction Low molecular mass organogelators (LMOGs) have received increasing attention during the last two decades because

• organogelators [22]. The steroidal LMOGs usually have substituents attached to the 3β-OH of the cholestane A ring and synthetic variations at the steroidal skeleton are scarce. Cholesterol-based LMOGs build mesophases in which steroid–steroid stacking is controlled by van der Waals forces. These interactions

Protonation and deprotonation induced organo/hydrogelation: Bile acid derived gelators containing a basic side chain

• Uday Maitra and
• Arkajyoti Chakrabarty

Beilstein J. Org. Chem. 2011, 7, 304–309, doi:10.3762/bjoc.7.40

• organogelators have been reported [10][11][12][13][14][15]. Our group has previously reported charge-transfer interaction driven organogelation based on bile acid derived, and other donor molecules [16]. The present work describes efficient organo/hydrogelation by two bile acid-derived low molecular mass

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

• functionalization of the anomeric position and the 4- and 6-hydroxy groups. We have found that further derivatization of the glucose headgroup to form different glycolipids can result in organogelators [34][35][36][37]. Previously, we have systematically synthesized and studied the self-assembling properties of a

• of acyl chains to those in compounds 2–4. These can potentially lead to novel classes of organogelators. Results and Discussion In order to better understand the importance of the anomeric substituent of the sugar headgroup for self-assembly, we synthesized a series of esters of the headgroup 8 by a

• compounds 17A and 18A. The two diaryl esters 15A and 16A were also able to form gels in aqueous DMSO solution. Compared to the diesters, the monoesters were not as effective as organogelators; only the 2-pentynoate 9B was able to gelate aqueous DMSO, and the 2-benzoate 15B was able to form a gel in ethanol

Gelation or molecular recognition; is the bis-(α,β-dihydroxy ester)s motif an omnigelator?

• Peter C. Griffiths,
• David W. Knight,
• Ian R. Morgan,
• Amy Ford,
• James Brown,
• Ben Davies,
• Richard K. Heenan,
• Stephen M. King,
• Robert M. Dalgliesh,
• John Tomkinson,
• Stuart Prescott,
• Ralf Schweins and
• Alison Paul

Beilstein J. Org. Chem. 2010, 6, 1079–1088, doi:10.3762/bjoc.6.123

• molecular mass organogelators (LMOGS) is still elusive, although much research attempting to quantify the fundamental aspects of this fascinating phenomenon is underway [1][2][3][4][5]. A wide range of structurally diverse gelators have been identified, and in general, whilst a particular gelator functions

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

• aliphatic hydrocarbons (methylcyclohexane (MCH), cyclohexane, n-hexane, n-heptane) and in tetrachloroethylene the CGC values are even less than 0.1 wt %. Organogelators with such low CGC values are classified as supergelators [4], and thus the present quaterthiophene gelator T1 belongs to this category. The

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

• those of the shorter ones. Keywords: amino acids; hydrophobic effect; organogelators; self-assembly; urea; Introduction Organic gelators are an interesting group of molecules that are able to form a non-covalent three dimensional network with a particular solvent system. The ultimate result is the

• immobilization of solvent molecules. These molecules possess many potential applications in biomedical science, environmental and separation technology [1][2][3][4][5][6]. One key problem in the design and synthesis of organogelators lies in the difficulty in predicting their gelation properties beforehand. Most

• organogelation strength in aromatic solvents of a series of α-amino acid-based low molecular weight organogelators 1 (Figure 1) could be enhanced by appending additional aromatic-containing substituents [7]. Both the Cbz protecting group and the benzyl ester functionality were responsible for the enhanced

Insights into the mechanical properties of a silicone oil gel with a ‘latent’ gelator, 1-octadecylamine, and CO₂ as an ‘activator’

• Emiliano Carretti,
• Mathew George and
• Richard G. Weiss

Beilstein J. Org. Chem. 2010, 6, 984–991, doi:10.3762/bjoc.6.111

• ; gel-sol transition; rheology; viscosity; Introduction During the last two decades, research efforts have increased enormously to understand the range of structures and processes of self-assembly of ‘small’ molecules such as low-molecular-mass organogelators (LMOGs), which gelate large volume

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

• and coworkers have observed that the separate enantiomers assemble into fibers with opposite helicity while the racemic mixture yield nanoscale, spherical structures [15]. In order to create chiral response materials based on such systems, it would be interesting to develop organogelators that can be

• organogelators. Remarkably, our pure enantiomeric gelator could not be racemized in the gel phase, while racemization takes place in the self-assembled fiber state. We are currently studying this class of organogelator for the creation of responsive gels and attrition-enhanced solid-phase enantioenrichment

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

• ][9]. Compared to the well-known organogelators formed by the entanglement of usually crystalline fibers [10][11][12][13], supramolecular polymers display some specific features. In particular, hydrogen-bonded supramolecular polymers are often dynamic at room temperature, which means that they do not