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Photo-responsive liquid crystalline vitrimer containing oligoanilines

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Chinese chemical Letters 2017年第11期28卷 2139-2142页

作者： Qiaomei Chen Yen Wei Yan Ji moe key laboratory of bioorganic phosphorus chemistry & chemical biology Department of Chemistry Tsinghua University Beijing 100084 China

Liquid crystalline vitimers （LC-vitrimers） can be easily processed into complex three-dimensional configurations. In this paper, we present a photo-responsive LC-vitrimer by simply introducing a photo- thermal agent aniline trimer into the LC-vitrimer system. As aniline trimer acts as a curing agent, it can be homogeneously dispersed in the material, avoiding aggregation which commonly happens to nano- fillers. As a result, the resultant polymer not only can perform three light-controlled functions （welding, healing and shape memory）, but also can be prepared into aligned monodomain LC actuators with strains of about 40%-45%.

关键词： Liquid-crystalline elastomers Oligoanilines Transesterification Photo-thermal effect Actuators

Advances in tumor-endothelial cells co-culture and interaction on microfluidics

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Journal of Pharmaceutical Analysis 2018年第4期8卷 210-218页

作者： Weiwei Li Mashooq Khan Sifeng Mao Shuo Feng Jin-Ming Lin Department of chemistry Beijing Key Laboratory of Microanalytical Methods and Instrumentation MOE Key Laboratory of Bioorganic Phosphorus Chemistry& Chemical Biology Tsinghua University

The metastasis in which the cancer cells degrade the extracellular matrix （ECM） and invade to the sur- rounding and far tissues of the body is the leading cause of mortality in cancer patients, With a lot of advancement in the field, yet the biological cause of metastasis are poorly understood, The microfluidic system provides advanced technology to reconstruct a variety of in vivo-like environment for studying the interactions between tumor ceils （TCs） and endothelial ceils （ECs）. This review gives a brief account of both two-dimensional models and three-dimensional microfluidic systems for the analysis of TCs-ECs co- culture as well as their applications to anti-cancer drug screening, Furthermore, the advanced methods for analyzing cell-to-cell interactions at single-cell level were also discussed,

关键词： Microfluidic Cell analysis Cell co-culture Cell interaction Review

Efficient synthesis of cyclic imides by the tandem N-arylation-acylation and rearrangement reaction of cyanoesters with diaryliodonium salts

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Chinese chemical Letters 2023年第5期34卷 281-285页

作者： Zhiyuan Bao Chao Chen moe key laboratory of bioorganic phosphorus chemistry&chemical biology Department of ChemistryTsinghua UniversityBeijing 100084China

Available online An efficient method for the synthesis of multi-substituted cyclic imides was developed with cyanoesters and diaryliodonium *** method proceeds through a cascade of N-arylationacylation and rearrangement to give target heterocycles in good yields(up to 99%).This method has the major advantages of a broad substrate scope,excellent functional group *** strategy was also extended to the fused cyclic imides,such as malonimides,succinimides and glutarimides.

关键词： Cyclic imides Cyanoesters Diaryliodonium salts N-Arylation-acylation Rearrangement

Coronarenes: recent advances and perspectives on macrocyclic and supramolecular chemistry

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Science China chemistry 2018年第8期61卷 993-1003页

作者： Mei-Xiang Wang moe key laboratory of bioorganic Phosphorous chemistry & chemical biology Department of Chemistry Tsinghua University

Synthetic macrocyclic host molecules always play an essential role in the establishment and development of supramolecular chemistry. Along with the continuous interests in the study of classical macrocycles, recent decades have witnessed the emergence and rapid development of the chemistry and supramolecular chemistry of novel and functional macrocycles. Owing to their easy availability, a self-tunable V-shaped cavity resulted from 1,3-alternate conformation, and diversified electronic features steered by the interplay between heteroatom linkages and aromatic rings, heteracalixaromatics act as a type of versatile and powerful macrocyclic hosts in molecular recognition and fabrication of supramolecular systems. Very recently, by means of engineering the bond connectivity or the recombination of chemical bonds within heteracalixaromatics, we have devised coronarenes, a new generation of macrocycles. In this concise review, macrocyclic and supramolecular chemistry of coronarenes are summarized in the order of their syntheses, structural features, molecular recognition and self-assembly properties. In the last part of this article, personal perspectives on the study of macrocyclic and supramolecular chemistry will also be discussed.

关键词： coronarenes heteracalixaromatics macrocycles molecular recognition non-covalent bond interactions

Appraisal of an oligomerization behavior of unprotected carbohydrates induced by phosphorus reagent

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Science China chemistry 2018年第2期61卷 243-250页

作者： Hang Yuan Xu Yang Peng Chen Yan Liu Guo Tang Yufen Zhao Department of chemical biology College of Chemistry and Chemical Engineering Key Laboratory for Chemical Biology of Fujian ProvinceXiamen University key laboratory of bioorganic phosphorus chemistry and chemical biology Ministry of Education Department of Chemistry Tsinghua University

In this article, a novel oligomerization behavior of unprotected monosaccharides was discovered in a one-pot reaction induced by phosphorus reagent at room temperature. The inherent characteristics of the oligomerization reaction were dissected in detail by mass spectrometry based method combined with NMR technology. It was found that the main glycosidic bonding pattern is (1→6) linkage with 66% regioselectivity for each step. The ratio of α-(1→6) and β-(1→6) glycosidic bonds formed is around 1:1. The reactivity of 1-OH group from aldoses and the driving force from penta-coordinated phosphorus intermediates are the two critical factors for the oligomerization, according to the monitoring experiments by ESI-MS and NMR. Besides, the oligomerization reaction has good compatibility for various aldoses and could expand to O-glycosylated modification of peptides in vitro. The above results will provide a novel enlightenment to develop more convenient and higher-efficient methods for the synthesis of oligosaccharide library.

关键词： organic phosphorus activation oligosaccharide oligomerization one-pot unprotected synthesis

Concise synthesis of xanthones by the tandem etherification——Acylation of diaryliodonium salts with salicylates

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Chinese chemical Letters 2018年第6期29卷 985-988页

作者： Gaoxiaozheng Liu Chao Wu Bifeng Chen Ru He Chao Chen moe key laboratory of bioorganic phosphorus chemistry & chemical biology Department of Chemistry Tsinghua University The Graduate School at Shenzhen Tsinghua University

An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation to give target heterocycles in good yields（up to 91%）. Multi-substituted xanthones were gained by shifting the substituent of salicylates or diaryliodonium salts

关键词： Xanthone Diaryliodonium salts Etherification Acylaion Multiple substituent

Synthesis of Ras proteins and their application in biofunctional studies

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Chinese chemical Letters 2018年第7期29卷 1043-1050页

作者： Jun Hu Pengcheng Zhu Yanmei Li Yongxiang Chen key laboratory of bioorganic phosphorus chemistry and chemical biology(Ministry of Education) Department of ChemistryTsinghua University

Approximately 30% of human cancers are associated with RAS mutation. Ras proteins on the plasma membrane regulate a plenty of important cellular processes. The post-translational modifications(PTMs)of Ras proteins like lipidation and methylation are crucial for their correct cellular localization and biological function. Hence, obtaining Ras proteins with different kinds of modifications is the necessary prerequisite to investigate their biological properties at molecular level. In this review, we mainly summarize the developed strategies including chemical total synthesis, biosynthesis and semi-synthesis for producing Ras proteins with modifications and their application in biological studies.

关键词： Ras Lipopeptides Semi-synthesis Multi-PTMs Biophysical function

Construction and Functionalization of Highly Strained N-Doped Zigzag Hydrocarbon Belts

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CCS chemistry 2023年第1期5卷 117-123页

作者： Ming Xie Shuo Tong Mei-Xiang Wang moe key laboratory of bioorganic phosphorus chemistry and chemical biology Department of ChemistryTsinghua UniversityBeijing 100084

Recent years have witnessed breakthroughs in the study of zigzag hydrocarbon ***,the synthesis of heterocycle-containing zigzag molecular belts remains very rare and challenging despite their interesting structures and potential applications in chemistry and materials ***,we report the expeditious construction of a highly strained belt[4]arene[4](1,4-dihydropyridine)structure using the fjords-stitching *** synthesis comprised four-fold abnormal m-bromination of four Npivaloylaniline units and Pd_(2)(dba)_(3)/4-Me_(2)NC_(6)H_(4)Pt Bu_(2)-catalyzed intramolecular C-N bond-forming *** functionalization through Narylations produced a variety of tetraza-embedded octahydrobelt[8]*** oxidation of p-methoxyphenyl-substituted belt[4]arene[4](1,4-dihydropyridine)with Ag[Al(O^(t)Bu^(F))^(4)]yielded a singlet diradical dication N-doped zigzag belt.

关键词： zigzag molecular belt cyclacene octahydrobeltarenepyridine meta-bromination of Nacylaniline palladium-catalyzed C-N bond formation diradical dication salt

A microchip to analyze single crystal growth and size-controllability

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Science China chemistry 2009年第7期52卷 1014-1020页

作者： PANG YuanFeng LIU JiangJiang LI HaiFang LIN JinMing The key laboratory of bioorganic phosphorus chemistry and chemical biology Department of ChemistryTsinghua UniversityBeijing 100084China

A microfluidic device to control single crystallization on the micron scale has been developed. The salt solution was stored in the nano-volume gaps between the arrays of protrudent circular plots in the microchip. The mixed organic solvent was injected into the chip as the counter diffusion phase for crystallization forming. This device provides a liquid-liquid interface through which only one phase flows while the other stays at the fixed plot. Therefore, it is possible to control the position of crystallization on the fixed plot. We can control the size and the uniformity of single crystals from 5 to 50 μm in length by adjusting the relative factors, such as interface lifetime, breeds of the mix-organic solvents and injecting velocities. The longer interface lifetime and lower organic solvent injecting velocities can bring up larger and more asymmetric crystals, which nearly shows the same trend compared with the macroscopic crystallization. Finally, the effect of the surfactant on the crystallization in the microdevice was studied. By adding the surfactant into the liquid-liquid interface, smaller sizes of crystals can be obtained without changing the crystal configuration.

关键词： microfluidic device single crystallization liquid-liquid interface size controllability