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We report a novel orthogonal combination of cationic and radical RAFT polymerizations to synthesize bottlebrush polymers using two distinct RAFT agents. Selective consumption of the first RAFT agent is used to control the cationic RAFT polymerization of a vinyl ether monomer bearing a secondary dormant RAFT agent, which subsequently allows side‐chain polymers to be grafted from the pendant RAFT agent by a radical‐mediated RAFT polymerization of a different monomer, thus completing the synthesis of bottlebrush polymers. The high efficiency and selectivity of the cationic and radical RAFT polymerizations allow both polymerization to be conducted in one‐pot tandem without intermediate purification.
While poly(acyclic orthoesters) (PAOEs) have many appealing features for drug delivery, their application is significantly hindered by a lack of facile synthetic method. Here we report a simple method for synthesizing acyclic diketene acetal monomers from diols and vinyl ether, and their polymerization with a diol to first synthesize PAOEs. The PAOEs rapidly hydrolyzed at lysosomal pH. With the help of a cationic lipid, ovalbumin, a model vaccine antigen, was efficiently loaded into PAOEs nanoparticles using a double emulsion method. These nanoparticles efficiently delivered ovalbumin into the cytosol of dendritic cells and demonstrated enhanced antigen presentation over PLGA nanoparticles. PAOEs are promising vehicles for intracellular del.
A powerful palladium‐catalyzed dearomative cyclization is developed, providing a facile entry to eight types of bridged tetracyclic skeletons bearing various ring sizes and heterocycles. With this method, several skeletons or analogs of natural products including tubingensin B and dracaenones are synthesized. Asymmetric dearomative cyclization enables various enantiomerically enriched bridged polycyclic systems with up to 99% ee by employing a chiral palladium catalyst.
A new generation of saturated benzene mimics ‐ 2‑oxabicyclo[2.1.1]hexanes, ‐ was developed. These compounds were designed as analogues of bicyclo[1.1.1]pentane with an improved water solubility. Crystallographic analysis of 2‑oxabicyclo[2.1.1]hexanes revealed that they occupy a novel chemical space, but at the same time resemble the fragment of meta ‐disubstituted benzenes.
Understanding of catalyst deactivation represents one of the major challenges in methanol‐to‐hydrocarbons (MTH) reaction over acidic zeolites. Here we report the critical role of intermolecular π‐interactions in catalyst deactivation in the MTH reaction on H‐SSZ‐13 and H‐ZSM‐5 zeolites. The π‐interaction induced spatial proximities/interactions between cyclopentenyl cations and aromatics in the confined channels and/or cages of zeolites are revealed by two‐dimensional solid‐state NMR spectroscopy. The formation of naphtalene as precursor to coke species is favored by the alkylation of aromatics with the proximate cyclopentenyl cations, which can correlate with the acid density and zeolite topology.
In this study, heteroatom‐containing spiropolymers were constructed in a facile manner by a catalyst‐free multicomponent spiropolymerization route. P1a2b as the most potent of these spiropolymers, demonstrates cluster‐triggered emission resulting from strong interactions with the MDM2 protein. By preventing the anti‐apoptotic p53/MDM2 interaction, P1a2b triggers apoptosis in cancerous cells, while demonstrating a good biocompatibility and non‐toxicity in non‐cancerous cells. The combined results from solution and cell‐based cluster‐triggered emission studies, docking, protein expression experiments and cytotoxicity data strongly support the MDM2‐binding hypothesis and indicate a potential application as a fluorescent cancer marker as well a.
We report a reaction platform for the synthesis of three different high‐value specialty chemical building blocks starting from bio‐ethanol, which might have an important impact in the implementation of biorefineries. First, oxidative dehydrogenation of ethanol to acetaldehyde generates an aldehyde‐containing stream active for the production of C 4 aldehydes via base‐catalyzed aldol‐condensation. Then, the resulting C 4 adduct is selectively converted into crotonic acid via catalytic aerobic oxidation (90 % yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 70 % yield of β‐hydroxy acid (3‐hydroxybutanoic acid). By controlling the pH of the reaction media, it is possible to hydrolyze the oxirane moiety leading
Reported here is a molecular‐Lego synthetic strategy for macrocycles with functional skeletons, involving one‐pot and high‐yielding condensation between bis(2,4‐dimethoxyphenyl)arene monomers and paraformaldehyde. By changing the blocks, variously functional units (naphthalene, pyrene, anthraquinone, porphyrin, et. al.) can be conveniently introduced into the backbone of macrocycles. Interestingly, the macrocyclization can be tuned by the geometrical configuration of monomeric blocks. Linear (180 o ) monomer yield cyclic trimers and pentamers, while V‐shaped (120 o , 90 o and 60 o ) monomers tend to form dimers. More significantly, even heterogeneous macrocycles are obtained in moderate yield by co‐oligomerization of different monomers. Thi.
For the first time, the monoalkoxycarbonylation of easily available 1,3‐diynes to give synthetically useful conjugated enynes has been realized. Key to success was the design and utilization of the new ligand 2,2'‐bis( tert ‐butyl(pyridin‐2‐yl)phosphanyl)‐1,1'‐binaphthalene ( L12 , Neolephos), which permits the palladium‐catalyzed selective carbonylation under mild conditions, providing a general preparation of functionalized 1,3‐enynes in good to high yields with excellent chemoselectivities. Synthetic applications, which showcase the possibilities of this novel methodology include an efficient one‐pot synthesis of 4‐aryl‐4 H ‐Pyrans as well as the rapid construction of various heterocyclic, bicyclic, polycyclic compounds.
Propene/propane separation has always been a challenging endeavor due to the very small variance in molecular sizes, boiling points and condensabilities between these molecules. Herein, we report a strategy of introducing ZIF fragments into traditional mordenite (MOR) zeolite to decorate the 12‐membered ring of MOR. After decoration, the originally ineffectual zeolite MOR exhibited high kinetic propene/propane selectivities (139 at 25 °C) and achieved efficient propene/propane separation. The propene/propane separation potentials of the resulting adsorbents were further confirmed by breakthrough experiments for equimolar propene/propane (50/50) mixtures.
The stereospecific polycyclic core formation of hapalindoles and fischerindoles is controlled by the Stig cyclases through a three‐step cascade involving Cope rearrangement, 6‐ exo ‐trig cyclization and a final electrophilic aromatic substitution. Here we report a comprehensive study of all currently annotated Stig cyclases, and reveal that these proteins can assemble into heteromeric complexes induced by Ca 2+ to cooperatively control the stereochemistry of hapalindole natural products.
A soluble and stable core‐modified [38]octaphyrin MC‐T8 containing eight thiophene rings was synthesized by a new Yamamoto‐coupling‐followed‐by‐oxidative dehydrogenation protocol. X‐ray crystallographic analysis revealed a nearly planar backbone, and the molecule is globally aromatic with a dominant 38π conjugation pathway. The dication MC‐T8 2+ is antiaromatic and the backbone is distorted, with a different orientation of the thiophene rings. The tetracation MC‐T8 4+ becomes aromatic again, with a shallow bowl‐shaped geometry. Both the neutral and dication demonstrated open‐shell diradical character with a small singlet‐triplet energy gap (‐2.70 kcal/mol of MC‐T8 and ‐3.78 kcal/mol for MC‐T8 2+ ), and they are stable due to effective spin
The use of synthetic bridges as surrogates for disulfide bonds has emerged as a practical strategy to obviate the poor stability of some disulfide‐containing peptides. However, peptides incorporating large‐span synthetic bridges are still beyond the reach of existing methods. Here we report a native chemical ligation (NCL)‐assisted diaminodiacid (DADA) strategy that enables the robust generation of disulfide surrogate peptides incorporating surrogate bridges up to 50 amino acids in length. This strategy provides access, for this first time, to some highly desirable but otherwise impossible‐to‐obtain disulfide surrogates of bioactive peptides, including μ‐conotoxin KIIIA, a potent inhibitor of voltage‐gated sodium channels. The bioactivities.
In the field of chiral Brønsted base catalysis, a new generation of chiral catalysts has been highly anticipated to overcome the intrinsic limitation of pronucleophiles that are applicable to the enantioselective reactions. Herein, we reveal conceptually new chiral Brønsted base catalysts consisting of two different organobase functionalities, one of which functions as an organosuperbase and the other as the substrate recognition site. Their prominent activity, which stems from the distinctive cooperative function by the two organobases in a single catalyst molecule, was demonstrated in the unprecedented enantioselective direct Mannich‐type reaction of α‐phenylthioacetate as a less acidic pronucleophile. The present achievement would provid.
Zeolitic Imidazolate Framework (ZIF) biocomposites show the capacity to protect and deliver bio‐therapeutics. To date, the progress in this research area is based on laboratory batch methods. To further explore the potential of ZIF‐biocomposites for application to biomedicine and biotechnology, the continuous production of ZIF‐biocomposites of specific particle size is desirable. Here we report the first continuous flow synthetic method for the encapsulation of a model protein (bovine serum albumin, BSA) and a clinical therapeutic (α1‐antitrypsin, AAT) in ZIF‐8. We studied the in situ kinetics of nucleation, growth and crystallization of BSA@ZIF‐8 by small angle X‐ray scattering. By controlling the injection time of ethanol, we could quench.
Antimony(III) borates with stereochemical active lone pair remains a huge blank, despite that the first antimony borate has been reported for more than twenty years. Herein, we successfully synthesize the first antimony(III) borate in closed system, namely SbB 3 O 6 . Remarkably, SbB 3 O 6 not only exhibits an exceptional linear optical response, that is, birefringence of ∆ n =0.290 at the wavelength of 546 nm, which is the largest among borates, but also has a strong nonlinear optical response of 3.5 times larger than the benchmark KH 2 PO 4 , which exceeds those of most borates. Theoretical calculations reveal that the coexistence of strong linear and nonlinear optical responses in SbB 3 O 6 should be attributable to the synergistic effec.
The crosslink‐enhanced emission effect was first proposed to explore the strong luminescence of non‐conjugated polymer dots only possessing either non‐ or weakly‐emissive sub‐luminophores. Interesting phenomena in recent research indicate such enhancement caused by extensive crosslinking appears in diverse luminescent polymers with sub‐luminophores (electron‐rich hetero‐atomic moieties) or luminophores (conjugated π domains). This enhancement can promote the emission from non‐luminous to luminous, weakly‐luminous to strongly‐luminous and even converting the pathway of radiative transitions. The concept of the crosslink‐enhanced emission effect should be updated and extended to an in‐depth spatial effect, such as electron overlap and energy
Pre‐targeted strategies combine high specificity of macromolecules such as antibodies for target binding and rapid clearance of small molecular ligands to image target molecules. However, pre‐targeted imaging of the activity of enzymes has not been described likely due to the lack of a mechanism to retain the injected substrate in the first step for subsequent labeling. Here we report the use of two bioorthogonal reactions—the condensation reaction of aromatic nitriles and aminothiols, and the inverse‐electron demand Deals‐Alder reaction (IEDDA) between tetrazine and trans‐cyclooctene (TCO) —to develop a novel strategy for pre‐targeted imaging of the activity of proteases. The substrate probe bearing TCO (TCO‐C‐SNAT4) can be selectively act.
A tetragold(I) rectangle‐like metallocage containing two pyrene‐bis‐imidazolylidene ligands and two carbazolyl‐bis‐alkynyl linkers is used for the encapsulation of a series of polycyclic aromatic hydrocarbons (PAHs), including corannulene. The binding affinities obtained for the encapsulation of the planar PAHs guests in CD2Cl2 are found to exponentially increase with the number of p‐electrons of the guest (1.3 > logK > 6.6). For the bowl‐shaped molecule of corannulene, the association constant is much lower than the expected one according to its number of electrons. The molecular structure of the host:guest complex formed with corannulene shows that the molecule of the guest is compressed, while the host is expanded, thus showing an unusua.

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