Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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

• the derivatives was moderate to excellent with a minimum gelation concentration ranging between 0.5–4.0% w/v and a gel–sol transition temperature range of 31–75 °C. 1,8-Bis(trityloxy)octane, the ditrityl derivative of 1,8-octanediol was the most efficient organogelator. Detailed characterizations of

• unit which may be further exploited in the design of small molecule based gelators. Keywords: hydrophobic interactions; organogelator; SEM; triphenylmethyl group; xerogel; Introduction Small organic molecules capable of forming gels are called low molecular weight gelators (LMWGs) [1][2][3]. These

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

• . Obviously, the gel from ethanol mainly shows a similar flower-like morphology. When we focused on the isopropanol xerogel, we could see that there are many regularly three-dimensional network structures. In 1-butanol, the organogelator molecules in the gel phase were self-assembled into tightly staked rods

Synthesis and characterization of pH responsive D-glucosamine based molecular gelators

• Navneet Goyal,
• Hari P. R. Mangunuru,
• Bargav Parikh,
• Sonu Shrestha and
• Guijun Wang

Beilstein J. Org. Chem. 2014, 10, 3111–3121, doi:10.3762/bjoc.10.328

• ; naproxen; organogelator; pH responsive; self-assembly; Introduction Low molecular weight gelators (LMWGs) have drawn great attention over the past few decades due to the formation of supramolecular structures and their potential applications as advanced materials [1][2][3][4][5][6][7]. LMWGs are also

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

• -organogelator for hydrocarbons. The scope of solvent gelation was analysed with regard to two solvent parameters, namely the Kamlet–Taft and the Hansen solubility parameters. The best correlation was observed with the Hansen approach that revealed the existence of two clear gelation zones. We propose a general

• promote the one-dimensional growth. These concepts have been recently exploited to design new LMOGs [15][16]. Nevertheless, the presence of a supramolecular synthon in a molecule is a necessary but not a sufficient feature to become an organogelator. The formation of the gel involves a delicate balance of

• an aromatic moiety (A) connected to a steroidal group (S) through a linker (L). Since then a great number of ALS molecules have been discovered constituting the most systematically investigated family of LMOGs [24]. Recently we have reported a new steroid-based organogelator with a non-conventional

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

• . Keywords: bile acid derived amines; organogelator and hydrogelator; protonation and deprotonation induced gelation; SEM and POM; thermal stability; Introduction Low molecular mass organo- and hydrogelators (LMOG) have attracted considerable attention in recent years due to their tunable physical

• carried out with compounds 1 and 2 in various organic and mixtures of aqueous organic solvents (Experimental section); the results of the gelation studies are summarized in Table 1. (B) Protonation–deprotonation induced gelation The organogelator 1 was found to be a non-gelator in its neutral form

• conclusion, we have demonstrated an interesting protonation and deprotonation induced gelation of an organogelator and a hydrogelator, respectively. Using cresol red as an indicator, it was possible to illustrate the acid-stability and base-instability of the organogel and the acid-instability and base

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

• synthesis and characterization of these novel analogs are reported. Keywords: 1,5-anhydroglucitol; carbohydrate; hydrogelator; organogelator; self-assembly; Introduction In recent years, the field of low molecular weight gelators (LMWGs) has received a great deal of attention. LMWGs are an interesting

Amphiphilic dendritic peptides: Synthesis and behavior as an organogelator and liquid crystal

• Baoxiang Gao,
• Hongxia Li,
• Defang Xia,
• Sufang Sun and
• Xinwu Ba

Beilstein J. Org. Chem. 2011, 7, 198–203, doi:10.3762/bjoc.7.26

• organogels assembled from G3 formed thin fibres that underwent further aggregation to form fibre bundles. These fibre bundles constitute a highly developed entangled network. Figure 2 shows the XRD scan of organogelator G3 and liquid crystal G3. Being different from the liquid crystal, the XRD of

• organogelator shows no reflection peaks in the small-angle region which indicates that molecular arrangement in the organogelator is disordered. Figure 3 shows the FT-IR of G3 as an organogelator and as a liquid crystal. The absorption at 3081 cm−1 is ascribed to the N–H stretching frequency of the hydrogen

• bonds. The absorption intensity at 3081 cm−1 decreases in the organogelator which indicates the loss of hydrogen bonds. Hydrogen bonds as physical cross-linking points in these compounds are an essential factor for gelling. With more physical cross-linking points, compound G3 gels more easily. Compound

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

• research. Keywords: gelation; inelastic neutron spectroscopy; low molar mass organogelator; neutron scattering; neutron spin-echo scattering; self-assembly; Introduction A detailed, molecular level understanding of the fundamental aspects of the spontaneous self-assembly and network formation of low

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

• of donor and acceptor materials plays a prominent role in device performance [25]. Recently, we reported that a n-type perylene bisimide organogelator exhibits photovoltaic activity with a p-type semiconducting polymer [26]. In this work, as an initial study we characterized the morphology of a

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

• often a subtle change of the substituents of the organgelator can lead to substantial modification in its gelating properties. This is because gelation is the result of a delicate balance of various driving forces. If the binding interactions between the organogelator molecules are too strong

• , precipitation or crystallization will take place. On the other hand, if the interactions are too weak, dissolution of the organogelator will result. In addition, non-specific interactions such as hydrophobic and van der Waals interactions are difficult to quantify, yet they can play very important roles on a

• poor organogelators, while the longer aliphatic chain analogues (n ≥ 10) formed transparent gels in aromatic solvents and translucent gels in 1,4-dioxane, DMF and DMSO. Most interestingly, it was observed that organogelator 2 (n = 20) with the longest hydrocarbon chain also formed opaque gels in

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

• organogelator has been synthesized that can be racemized and self-assembled in apolar solvents whilst at higher concentrations organogels are formed. Field emission scanning and transmission electron microscopy revealed the formation of bundle fibrils that are able to gelate the solvent. 1H NMR studies showed

• hydrogen-bond interactions between the peptide head groups of neighbouring organogelator molecules. The enantiomerically pure organogelator can be racemized by the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as was evident from chiral high-performance liquid chromatography analysis. Keywords: chirality

• racemized by a stimulus [16][17]. In the current manuscript we report our attempt to synthesize a racemizable chiral organogelator (Scheme 1). The molecular design of our organogelator (3) is based on a finding that the imine of 2-methylbenzaldehyde and phenylglycinamide can be racemized in the presence of