Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

• Lorenzo Catti,
• Shinji Aoyama and
• Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

• present amphiphile is originated from bent aromatic amphiphile AA [12][13], composed of two anthracene panels linked by a m-phenylene spacer with two cationic side-chains, which assembles into an aqueous ≈2 nm-sized aromatic micelle with broad host functions [14][15][16][17][18][19][20][21]. Replacement

• , amphiphiles PA-OCH3 and PA-OH were synthesized by reacting prePA under neat conditions with 1-(2-bromoethoxy)-2-(2-methoxyethoxy)ethane (67% yield over 2 steps after ion-exchange) and 2-[2-(2-chloroethoxy)ethoxy]ethanol (42% yield), respectively (Figure 2b). Imidazole-functionalized amphiphile PA-Im was

• an improved C60-solubilization efficiency (up to 1.6-fold), compared to previous amphiphile AA bearing ionic side-chains [17]. The improvement presumably stems from the increased flexibility of the anthracene panels and decreased electrostatic repulsion between the cationic moieties, allowing for

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• on TBTQ-C6/CS-TPE supra-amphiphile, which may have potential applications in oral drug delivery materials and biomarkers. Results and Discussion Synthesis and characterization of CS-TPE. The host molecule TBTQ-C6 was synthesized as reported in our previously reported method [16]. Three CS-TPE

• improved water solubility of the supra-amphiphile due to the highly water-soluble behavior of TBTQ-C6 under alkaline conditions in its carboxyl anion form. As a result, the polymer chains were extended, releasing the entanglement and wrapping of the TPE fluorogens, thereby reducing the emission of the

• successfully designed and synthesized different degrees of TPE-labelled CS polymer compounds that exhibit the AIE fluorescence effect and we constructed pH-responsive fluorescent supramolecular spherical nanoparticles based on CS-TPE alone and the host–guest TBTQ-C6/CS-TPE supra-amphiphile. The critical

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• -containing amphiphile (trans-AZO) to produce the TBTQ-C6-trans-AZO supra-amphiphile by host–guest interactions in water. The supra-amphiphile was further self-assembled into photo and pH dual-responsive supramolecular vesicles that have a potential to serve as drug nanocarriers to enable controlled drug

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• Research Center of Electron Microscopy, Freie Universität Berlin, Fabeckstr. 34a, 14195 Berlin 10.3762/bjoc.17.10 Abstract The synthesis of a sulfate-modified dendritic peptide amphiphile and its self-assembly into one-dimensional rod-like architectures in aqueous medium is reported. The influence of the

• recently reported the successful application of functional supramolecular polymers in a biological context [30]. By decoration of the discotic peptide amphiphile monomers with dendritic mannose moieties, a specific cell targeting of macrophages and internalization in those antigen presenting cells has been

• towards L-selectin has been evaluated using surface plasmon resonance (SPR) experiments. Results and Discussion Dendritic peptide amphiphile design and synthesis Two different peptide amphiphiles were synthesized, i.e., a non-sulfated, neutral amphiphile I as well as a dPGS-coupled, sulfated amphiphile II

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

• PDI system with a hydrophilic group (phenoxybenzoic acid) attached to the aromatic core of PDI at the “bay area” [35]. Compound 1 is an asymmetric amphiphile that was designed to result in arrays that differ from fibrous and monolayer structures assembled from symmetrically substituted PDI systems [36

Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response

• Rakesh Biswas,
• Surya Ghosh,
• Shubhra Kanti Bhaumik and
• Supratim Banerjee

Beilstein J. Org. Chem. 2020, 16, 2728–2738, doi:10.3762/bjoc.16.223

• buffer and also in buffer containing 150 mM NaCl at physiological pH value. Furthermore, the multivalent aggregates demonstrated a significant selectivity in ATP detection over ADP, AMP and pyrophosphate. Keywords: amphiphile; ATP; excimer; multivalency; self-assembly; Introduction Supramolecular anion

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• . These fullerenol amphiphiles can serve as suitable precursors for further reactions resulting in new applications for fullerenols. Keywords: amphiphile; C60Cl6; fullerene; fullerenol; one-pot; Introduction The roman god Janus, who is typically depicted with two faces, metaphorically stands for duality

• amphiphile with dimethoxyaniline as substituent (all characterization data can be found in Supporting Information File 1). ESIMS (Figure 1a) shows a rather complex fragmentation pattern similar to unsubstituted fullerenol compounds known in the literature [33]. The general complexity of the spectrum derives

• with ESIMS, TGA and MAS NMR. These compounds can serve as precursors for further modified fullerenols or as true surfactants. Characterization of fullerenol amphiphile with substituent 1. a) ESIMS in positive mode, molecular ion peak marked with circle, b) TGA under nitrogen with 5 K/min, c) MAS-NMR

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• its structure, resulting in a non-ionic amphiphile (Figure 2). In water, PTS forms nanomicelles which contribute to the solubilization of water-insoluble substrates and catalysts, thus contributing significantly to improve olefin metathesis yields. The positive effect of this strategy was demonstrated

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• was elaborated for the naked-eye detection of ADP with a detection limit of 0.5 mM. Keywords: ADP; amphiphile; ATP; calix[4]arene; CuAAC; eosin Y probe; molecular recognition; polydiacetylene; self-assembly; triazole; Introduction During the last two decades many researcher groups have paid much

• vesicles [41]. The inflection point in the plot of EY λmax vs surfactant concentration should be treated as the CAC of the amphiphile [42]. As can be seen from Table 1 the CAC values determined by the two methods are significantly different, especially in the case of macrocycles 10a,b. These differences

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• processes [50]. In the case of amphiphiles, these phenomena lead to the formation of compartments by self-assembly, which can encapsulate other solutes, e.g., RNA [17][51]. The accumulation ability of porous minerals allows for the amphiphile concentration to surpass their critical vesicle concentration to

• acid monomers has been achieved in this manner: When amphiphile vesicles or liposomes are dried in the presence of solutes on a silicate support, a system of stacked lipid bilayers with intercalated solutes is formed [52]. In this arrangement, the nucleotides are optimally spaced to react and form

• nucleic acid oligomers [53][54][55]. The presence of the mineral support is crucial here as it permits the preservation of the amphiphile bilayer structure during drying, thereby promoting the conversion of an “unreactive” organization (free floating vesicles and free monomers) into reactive chemical

Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

• Frederik Neuhaus,
• Fabio Zobi,
• Gerald Brezesinski,
• Marta Dal Molin,
• Stefan Matile and
• Andreas Zumbuehl

Beilstein J. Org. Chem. 2017, 13, 1099–1105, doi:10.3762/bjoc.13.109

• ]. Mechanical planarization in the ground state increases the conjugation of the push–pull system. As a result, the excitation (or absorption) maximum shifts up to 80 nm to the red [8]. An anionic headgroup is added to produce an amphiphile that self-assembles into monolayers and micelles and enters

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

• Simon Drescher,
• Vasil M. Garamus,
• Christopher J. Garvey,
• Annette Meister and
• Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

• DPPC/DHPC systems [49], or for mixtures of phospholipids with other amphiphilic substances, e.g., in PEG-stabilized bilayer systems [50][51], for phospholipids with membrane scaffold proteins [52][53] or in combination with copolymers [54][55], or for DPPC in mixture with a T-shaped amphiphile [56

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• products, to biomedical applications including MRI imaging agents [1][2][3], membrane-protein crystallisation media [4][5][6] and solubilising bioactive food additives (Figure 1) [7]. Furthermore, recent research has centred on the use of amphiphile nanoparticles for drug-delivery applications [8][9][10

• amphiphiles has been underexplored, generally due to technical difficulties in the synthesis and handling of such compounds [13]. Thus, a new method combining high-throughput synthesis and liquid-crystalline phase characterisation may open new territory in the field of amphiphile discovery. Furthermore

• , and to deepen the understanding of how molecular structure influences the characteristics of self-assembly. Previous amphiphile libraries have been prepared using a thiol–yne reaction [14] and an in situ hydrazone formation between aldehyde tails and hydrazide head groups [15] in order to study gene

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

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

• vs Gly-Gly-based hydrogelators. Previously, in our group, amino acid based amphiphiles i.e. Gly-Gly-His-EO2-Alk, a trimodular amphiphile (containing three domains: H-bond donor and acceptor/hydrophilic/hydrophobic domain, respectively) were reported to act as hydrogelators and that the gelation

• molecular structure in supramolecular self-assembling, i.e., the number of H-bond donor and acceptor amide moieties (3 in β-Ala-His-amphiphile vs 4 Gly-Gly-His-amphiphile) and consequently, to obtain further insights on the gelation mechanism. The hydrogels were characterised by a number of techniques

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

• originates from the interdigitated bilayer packing of the amphiphile leading to the development of an efficient hydrogel. Interestingly, the presence of the pyridinium scaffold along with the long alkyl chain render these amphiphiles inherently antibacterial. The amphiphilic hydrogelators exhibited high

• antibacterial activity against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values as low as 0.4 μg/mL. Cytotoxicity tests using MTT assay showed 50% NIH3T3 cell viability with hydrogelating amphiphile 2 up to 100 μg/mL. Keywords: antibacterial; bilayer structure

• properties to amphiphilic molecules [28][29][30][31]. The cationic charge of the amphiphile plays an instrumental role in disrupting the innate defense mechanism of microorganisms by disrupting the microbial cell membrane [32][33]. Hence, it would be interesting to develop amphiphilic hydrogelators that have