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1.
Ferran Gonzàlez de Rivera Lara-Isabel Rodríguez Oriol Rossell Miquel Seco Núria J. Divins Ignasi Casanova Jordi Llorca 《Journal of organometallic chemistry》2011,696(11-12):2287-2293
The synthesis and characterization of two new carbosilane dendrons functionalized in the focal point with a single thiol group is described. These molecules were used as stabilizing agents for the formation of gold nanoparticles. These materials were obtained by the reduction of hydrogen tetrachloroaurate phase-transferred into toluene in the presence of the carbosilane dendrons. The gold nanoparticle-cored dendrons (NCDs) were characterized by TEM, XPS, AFM, IR, UV, and NMR techniques. Average particle diameter ranged from 2.5 to 2.6 nm with narrow size distribution and remarkable stability; in particular, the elimination of the protecting shells to give naked gold, after NCDs deposition on a support, is more difficult using carbosilane dendrons than in the case of conventional dodecanethiol-protected gold nanoparticles. 相似文献
2.
Dr. Evgeny Apartsin Dr. Anne-Marie Caminade 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(72):17976-17998
This review presents precisely defined amphiphilic dendrons, their self-association properties, and their different uses. Dendrons, also named dendritic wedges, are composed of a core having two different types of functions, of which one type is used for growing or grafting branched arms, generally multiplied by 2 at each layer by using 1→2 branching motifs. A large diversity of structures has been already synthesized. In practically all cases, their synthesis is based on the synthesis of known dendrimers, such as poly(aryl ether), poly(amidoamine) (in particular PAMAM), poly(amide) (in particular poly(L-lysine)), 1→3 branching motifs (instead of 1→2), poly(alkyl ether) (poly(glycerol) and poly(ethylene glycol)), poly(ester), and those containing main group elements (poly(carbosilane) and poly(phosphorhydrazone)). In most cases, the hydrophilic functions are on the surface of the dendrons, whereas one or two hydrophobic tails are linked to the core. Depending on the structure of the dendrons, and on the experimental conditions used, the amphiphilic dendrons can self-associate at the air-water interface, or form micelles (eventually tubular, but most generally spherical), or form vesicles. These associated dendrons are suitable for the encapsulation of low-molecular or macromolecular bioactive entities to be delivered in cells. This review is organized depending on the nature of the internal structure of the amphiphilic dendrons (aryl ether, amidoamine, amide, quaternary carbon atom, alkyl ether, ester, main group element). The properties issued from their self-associations are described all along the review. 相似文献
3.
Núñez R Gonzalez-Campo A Laromaine A Teixidor F Sillanpää R Kivekäs R Viñas C 《Organic letters》2006,8(20):4549-4552
Small carbosilane dendrons in which a closo-carborane is located at the focal point have been prepared by a sequence of steps involving hydrosilylation and reduction reactions. These compounds are used as scaffolds for peripheral functionalization with styrene, chlorovinylstyrene, or suitable carboranes, while keeping the C(cluster)-Si (C(c)-Si) bond. Modification of the core by reduction of the carborane with Mg/BrCH2CH2Br was also achieved. 相似文献
4.
For the first time, the divergent synthesis of azide-functionalized PAMAM dendrons using azidopropyl amine as an azide focal point and convergent synthesis of symmetric PAMAM-like dendrimers containing 1,2,3-triazole rings as connectors via click chemistry with a dialkyne core is described. 相似文献
5.
Dendronized Anionic Gold Nanoparticles: Synthesis,Characterization, and Antiviral Activity
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Cornelia E. Peña‐González Pilar García‐Broncano Prof. M. Francesca Ottaviani Dr. Michela Cangiotti Dr. Alberto Fattori Margarita Hierro‐Oliva Prof. M. Luisa González‐Martín Dr. Jorge Pérez‐Serrano Dr. Rafael Gómez Prof. M. Ángeles Muñoz‐Fernández Dr. Javier Sánchez‐Nieves Dr. F. Javier de la Mata 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(9):2987-2999
Anionic carbosilane dendrons decorated with sulfonate functions and one thiol moiety at the focal point have been used to synthesize water‐soluble gold nanoparticles (AuNPs) through the direct reaction of dendrons, gold precursor, and reducing agent in water, and also through a place‐exchange reaction. These nanoparticles have been characterized by NMR spectroscopy, TEM, thermogravimetric analysis, X‐ray photoelectron spectroscopy (XPS), UV/Vis spectroscopy, elemental analysis, and zeta‐potential measurements. The interacting ability of the anionic sulfonate functions was investigated by EPR spectroscopy with copper(II) as a probe. Different structures and conformations of the AuNPs modulate the availability of sulfonate and thiol groups for complexation by copper(II). Toxicity assays of AuNPs showed that those produced through direct reaction were less toxic than those obtained by ligand exchange. Inhibition of HIV‐1 infection was higher in the case of dendronized AuNPs than in dendrons. 相似文献
6.
Murat Tonga Gulen Yesilbag Tonga Gonca Seber Ozgul Gok Amitav Sanyal 《Journal of polymer science. Part A, Polymer chemistry》2013,51(23):5029-5037
Dendronized copolymers bearing two different dendrons as side chains have been synthesized using a modular orthogonal “double‐click” reaction based strategy. The orthogonality of the Huisgen‐type azide‐alkyne cycloaddition and the Diels–Alder reaction was utilized to attach different dendrons to the polymer backbone via the “graft‐to” strategy. First through third generations of polyaryl ether dendrons appended with an alkyne group and polyester dendrons possessing a furan‐protected maleimide group at their focal point were reacted with a styrene based copolymer containing azide and anthracene moieties as side chains. The efficiency and selectivity of the orthogonal dendronization of the copolymers were examined via various analytical methods such as 1H NMR spectroscopy, FTIR and gel permeation chromatography. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51, 5029–5037 相似文献
7.
[structure: see text]. A new series of amphiphilic G1-G3 dendrons containing purely aliphatic hydrocarbon dendritic surface sectors and one or two carboxylic acid group(s) at the focal point was synthesized in good yields. The key branching steps involve diallylation reactions of diethyl malonate or Meldrum's acid. These dendrons are highly soluble in hexane despite having highly polar carboxylic acid groups at the focal point. 相似文献
8.
Synthesis and functionalization of dendron‐polymer conjugate based hydrogels via sequential thiol‐ene “click” reactions
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Sadik Kaga Tugce N. Gevrek Amitav Sanyal Rana Sanyal 《Journal of polymer science. Part A, Polymer chemistry》2016,54(7):926-934
Fabrication and functionalization of hydrogels from well‐defined dendron‐polymer‐dendron conjugates is accomplished using sequential radical thiol‐ene “click” reactions. The dendron‐polymer conjugates were synthesized using an azide‐alkyne “click” reaction of alkene‐containing polyester dendrons bearing an alkyne group at their focal point with linear poly(ethylene glycol)‐bisazides. Thiol‐ene “click” reaction was used for crosslinking these alkene functionalized dendron‐polymer conjugates using a tetrathiol‐based crosslinker to provide clear and transparent hydrogels. Hydrogels with residual alkene groups at crosslinking sites were obtained by tuning the alkene‐thiol stoichiometry. The residual alkene groups allow efficient postfunctionalization of these hydrogel matrices with thiol‐containing molecules via a subsequent radical thiol‐ene reaction. The photochemical nature of radical thiol‐ene reaction was exploited to fabricate micropatterned hydrogels. Tunability of functionalization of these hydrogels, by varying dendron generation and polymer chain length was demonstrated by conjugation of a thiol‐containing fluorescent dye. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 926–934 相似文献
9.
Ozgul Gok Sezin Yigit Meliha Merve Kose Rana Sanyal Amitav Sanyal 《Journal of polymer science. Part A, Polymer chemistry》2013,51(15):3191-3201
Diblock and triblock dendron–polymer conjugates containing biodegradable polyester dendron blocks and polyethylene glycol (PEG) polymer were synthesized using the Diels–Alder “click” cycloaddition reaction. PEG polymers with furan‐protected maleimide functionality were synthesized and reacted with biodegradable polyester dendrons containing an anthracene moiety at their focal point. First through third generations of biodegradable polyester dendrons containing an anthracene unit at their focal point were synthesized using a divergent strategy. Efficient conjugation of the dendrons to polymers was demonstrated using 1HNMR and size exclusion chromatography. This modular approach provides an easy access to the design of multivalent PEG conjugates. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3191–3201 相似文献
10.
Fréchet type dendritic benzyl propargyl ethers were synthesized by the reaction of propargyl bromide with the corresponding Fréchet type dendritic benzyl alcohol. A propargyl focal point functionalized dendrons were applied for the construction of symmetric and unsymmetric dendrimers containing 1,2,3-triazole rings as connectors via click chemistry with a tripodal azide core or a azide focal point functionalized Fréchet type dendrons. 相似文献
11.
Yuan You Yi Chen Chong Hua Chang‐Ming Dong 《Journal of polymer science. Part A, Polymer chemistry》2010,48(3):709-718
Dendron‐like poly(γ‐benzyl‐L ‐glutamate)/linear poly(ε‐caprolactone)/dendron‐like poly(γ‐benzyl‐L ‐glutamate) triblock copolymers having 2m + 1 PBLG branches (denoted as PBLG‐Dm‐PCL‐Dm‐PBLG, m = 0, 1, 2, and 3) were for the first time synthesized by utilizing ring‐opening polymerization (ROP) and click chemistry. The bifunctional azide‐terminated PCL (N3‐PCL‐N3) was click conjugated with propargyl focal point PAMAM‐typed dendrons Dm to generate Dm‐PCL‐Dm, which was then used as macroinitiator for the ROP of BLG‐NCA monomer to produce the targeted PBLG‐Dm‐PCL‐Dm‐PBLG triblock copolymers. Their molecular structures and physical properties were characterized in detail by FTIR, NMR, gel permeation chromatography, differential scanning calorimetry, and wide angle X‐ray diffraction (WAXD). The crystallinity of the central PCL segment within these copolymers is increasingly suppressed by the flanking PBLG wedges, whereas the PBLG segments gradually changed from a β‐sheet conformation to an α‐helix conformation with the increasing PBLG branches. These triblock copolymers formed thermoreversible organogels in toluene, and the dendritic topology of PBLG wedges controlled their critical gelation concentrations. The self‐assembled structure of organogels was further characterized by means of transmission electron microscopy, WAXD, and small‐angle X‐ray scattering. The fibers with flat ribbon morphology were clearly shown, and the gelation occurred through a self‐assembled nanoribbon mechanism. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 709–718, 2010 相似文献
12.
Wang BB Li WS Jia XR Gao M Ji Y Zhang X Li ZC Jiang L Wei Y 《Journal of colloid and interface science》2007,314(1):289-296
Three novel series of amphiphiles based on poly(amidoamine) dendrons (from G1 to G3) and having different aromatic chromophores (Cz I, Cz II, and Py) at the focal point were synthesized and studied for their self-assembly behavior in aqueous solution by using electronic microscopies (i.e., SEM and TEM), UV-vis, fluorescence, IR, and (1)H NMR spectroscopy. It was found that the generation of dendrons affected significantly the self-assembly of these amphiphiles in aqueous solution and the morphological structures of the resulting assemblies depended greatly on the architecture of the focal chromophores. As a result, the first generation of dendrons assembled readily into vesicles at low concentrations. These vesicular structures subsequently fused to form a stable tubular structure. Similar tubular structures could also be directly obtained through self-assembly of these amphiphilic dendrons at high concentrations. X-ray investigations showed that the resulting tubules possessed a lamellar structure. A head-to-head packing model of amphiphilic dendrons in the assemblies was proposed. 相似文献
13.
14.
Bilge Baytekin Dr. H. Tarik Baytekin Dr. Uwe Hahn Dr. Werner Reckien Dr. Barbara Kirchner Prof. Dr. Christoph A. Schalley Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(29):7139-7149
The mass spectrometric characterization of Fréchet‐type dendrons is reported. In order to provide the charges necessary for electrospray ionization, dendrons bearing an OH group at the focal point can be deprotonated and observed in the negative ion mode. Alternatively, the corresponding bromides can be converted to quaternary ammonium ions that can easily be detected in the positive mode. If the latter ions are subjected to collision‐induced dissociation experiments, a fragmentation cascade begins with the dissociation of the focal amine. The focal benzyl cation quickly decomposes in a fragmentation cascade from the focal point to the periphery until the peripheral benzyl (or naphthylmethyl) cations are formed. Five different mechanisms are discussed in detail, three of which can be excluded based on experimental evidence. The cascade fragmentation is reminiscent of self‐immolative dendrimers. 相似文献
15.
Synthesis and characterization of gold‐nanoparticle‐cored dendrimers (NCDs), in which the dendrons are attached to the gold core through gold–carbon bonds, are described. Synthesis of these materials involved the simultaneous reduction of HAuCl4 and a Fréchet‐type dendron with a diazonium group at the focal point, all in an organic solvent such as toluene. These materials possess a nanometer‐sized gold core surrounded by a shell of polyaryl ether dendrons, which are connected radially to the core. The NCDs were characterized by TEM, thermogravimetric analysis (TGA), and IR, UV, and NMR spectroscopic techniques. Average particle diameter of the NCDs ranged from 4.7 to 5.5 nm for the different generations. All NCDs exhibit the characteristic plasmon absorption of gold nanoparticles at 520 nm. Average numbers of dendrons per NCD in AuGn were calculated using results from TGA and TEM studies. Multiple layering of the dendrons is proposed as a possible reason for the high dendron/NCD value. 相似文献
16.
Yung‐Chung Chen Huey‐Ling Chang Rong‐Ho Lee Shenghong A. Dai Wen‐Chiung Su Ru‐Jong Jeng 《先进技术聚合物》2009,20(5):493-500
To investigate the dendritic structure effects on the electro‐optical (EO) coefficients and thermal stability of the nonlinear optical (NLO) active materials, a bifunctional compound, IDD (4‐isocyanato‐4′(3,3‐dimethyl‐ 2,4‐dioxo‐acetidino)‐diphenylmethane) was used as a building block to synthesize a series of novel NLO chromophore‐containing dendritic structures including Generation 0.5 (G0.5) to Generation 3 (G3). The glass transition temperatures (Tg) of G1–G3 dendrons were in the range of 76–116°C, whereas only the G0.5 dendron exhibited a melting temperature (Tm), 98°C. Moreover, a series of NLO‐active guest–host systems ranging from polyimide‐G0.5 (PI‐G0.5) to polyimide‐G3 (PI‐G3) were prepared by blending 20 wt% chromophore‐containing dendron with a high Tg polyimide. EO coefficients ranged from 6.1 to 12.9 pm/V. The r33/dye content ratio increased with increasing generation of dendron‐containing polyimide samples. Particularly, the improvement in r33/dye content ratio of PI‐G2.5 sample tripled as compared to that of the guest–host sample with Disperse Red 1. Excellent temporal stability of PI‐G0.5 and PI‐G1.5 at 80°C was obtained. Moreover, waveguide properties for NLO polymers containing higher generation dendrons (3.1–3.6 dB/cm at 830 nm) were also obtained. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
17.
Facile synthesis of second-generation dendrons with an aldehyde, epoxy, or t-Boc group at the focal point and nine carboxylic acid groups at the periphery is reported. The scheme includes a coupling of the first-generation dendrons and a two-step, one-pot reaction that proceeds through a Boc deprotection and in situ conjugation at the focal point. 相似文献
18.
Jae Wook Lee Hee Joo Kim Seung Choul Han Ji Hyeon Kim Sung‐Ho Jin 《Journal of polymer science. Part A, Polymer chemistry》2008,46(3):1083-1097
General, fast, efficient, and inexpensive methods for the synthesis of poly (amido amine) (PAMAM) dendrimers having core diversities were elaborated. In all syntheses, the major step involved an inexpensive 1,3‐dipolar cycloaddition reaction between an alkyne and an azide in the presence of Cu(I) species, which is known as the best example of click chemistry. The propargyl‐functionalized PAMAM dendrons are obtained by the divergent approach using propargylamine as an alkyne‐focal point. Three core building blocks, 1,3,5‐tris(azidomethyl)benzene, N,N,N′,N′‐tetra(azidopropylamidoethyl)‐1,2‐diaminoethane, and 4,4′‐(3,5‐bis(azidopropyloxy)benzyloxy)bisphenyl, were designed and synthesized to serve as the azide functionalities for dendrimer growth via click reactions with the alkyne‐dendrons. These three building blocks were employed together with the propargyl‐functionalized PAMAM dendrons in a convergent strategy to synthesize three kinds of PAMAM dendrimers with different core units. This novel and pivotal strategy using an efficient click methodology provides the fast and efficient synthesis of the PAMAM dendrimers with the tailed made core units. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 1083–1097, 2008 相似文献
19.
Wen‐Yu Chai Dr. Zi‐Fa Shi Peng An Wei Wang Lu‐Feng Wang Prof. Xiao‐Ping Cao 《化学:亚洲杂志》2012,7(1):143-155
The novel double‐stage convergent synthesis of a new class of polyisoprene terpenoid (PIPTP) dendrons is described. PIPTP dendrons bear a highly branched aliphatic hydrocarbon skeleton and a hydrophilic hydroxy focal point functionality. These dendrons have the specific formula C(5×2G+1‐5)H(5×2G+2‐8)O, and each dendritic layer is constructed from an isoprene unit. The key branching steps involve a double alkyl‐metal addition to an ester functionality, followed by deoxygenation of the resulting tertiary alcohol by triethylsilane and trifluoroacetic acid, then hydrogenation or hydrogenolysis. The dendrons were also attached to oligo(phenylene ethynylene)s (OPEs) so as to function as protective shells to allow fine tuning of the nanoscopic environment around the OPE moiety, and to exert precise control of the packing density and intermolecular interaction between the OPE cores. Fluorescence quantum yield data reveal that the OPE core is better encapsulated by the PIPTP dendrons than by Fréchet dendrons. 相似文献
20.
A straightforward method for the solid-phase synthesis of C-terminally modified polylysine dendrons has been developed by applying bisalkoxybenzaldehyde and trisalkoxybenzaldehyde linkers. The method has been used for the synthesis of polylysine dendrons with a variety of C-terminal ‘tail groups’ such as alkyl, propargyl, and dansyl to give dendrons in high crude purity. Furthermore, the method was successful for the synthesis of dendrons with multiple N-terminal pentapeptide groups together with C-terminal alkyl and propargyl tail groups. Finally, the method was shown to be well-suited for automated synthesis. 相似文献