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  • Sheng-Nan Lei, Huan Cong
    Chinese Chemical Letters. 2022, 33(3): 1493-1496.

    Because the widely used perfluorooctane sulfonate (PFOS) is harmful to both environment and human health, it is of great significance and urgency to develop sensitive and selective sensors for the detection of trace PFOS in water. In this study, a tetraphenylethylene-derived macrocycle BowtieCyclophane has been developed as a fluorescent sensor based on aggregation-induced emission enhancement and fluorochromism. Sensitive detection of PFOS has been achieved with a limit of detection (LOD) of 47.3 ± 2.0 nmol/L (25.4 ± 1.1 µg/L) accompanied by visual fluorescence color changes.

  • Yu-Shen Zhu, Linlin Shi, Lianrong Fu, Xiran Chen, Xinju Zhu, Xin-Qi Hao, Mao-Ping Song
    Chinese Chemical Letters. 2022, 33(3): 1497-1500.

    A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

  • Zhi-Lin Wu, Jin-Yang Chen, Xian-Zhi Tian, Wen-Tao Ouyang, Zhuo-Tao Zhang, Wei-Min He
    Chinese Chemical Letters. 2022, 33(3): 1501-1504.

    A novel and efficient electro-chemical initiated radical strategy was developed for the preparation of both N-substituted and N-unsubstituted 4-selanylisoquinolin-1(2H)-ones through selenylation of isoquinolin-1(2H)-ones with organodiselenides under chemical oxidant-, additive-free and ambient conditions.

  • Kai-Ran Zhang, Ming Hu, Jun Luo, Fengying Ye, Ting-Ting Zhou, Ying-Xue Yuan, Miao-Li Gao, Yan-Song Zheng
    Chinese Chemical Letters. 2022, 33(3): 1505-1510.

    A new tetraphenylethylene-cyclodextrin (TPE-CD) conjugate with a linkage composed of long triethylene glycol chain and triazole ring on the CD rim has been designed and synthesized. The TPE-CD conjugate exists in a stretched form in DMSO and enhances its fluorescence after addition of a small amount of water due to aggregation-induced emission (AIE) effect. However, in the presence of a large amount of water, the TPE unit will enter the cyclodextrin cavity to form a folded self-inclusion compound. In the self-inclusion compound, not only nitrogen-containing pseudo-crown ether is formed but also arouses photo-induced electron transfer (PET) process from nitrogen atoms of triazole ring to TPE unit and quenches the fluorescence although more aggregation occurs in more water. This is the first finding that TPE-macrocycle conjugate can form pseudo-crown ether and has both the AIE phenomenon and the PET effect. Interestingly, only mercury ion arouses the fluorescence recover of the self-inclusion compound by entering the pseudo-crown ether cavity and blocking the PET process by binding to the nitrogen atoms, while other tested metal ions almost have no effect on the fluorescence. Therefore, the TPE-CD conjugate can be used for the highly selective fluorescence "Turn-On" detection of Hg2+.

  • Ya Wang, Shiqiang Mu, Xin Li, Qiuling Song
    Chinese Chemical Letters. 2022, 33(3): 1511-1514.

    A facile synthesis of 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5 via [4 + 1] cyclization of ClCF2COONa with non-amine compounds containing amino groups is developed. Of note, this is the first time that halofluorinated compounds are used as C1 synthon to construct deuterated nitrogen-heterocyclic compounds. The current protocol features simple operation, readily accessible raw materials, wide substrate scope and valuable products

  • Jin Lin, Fang Wang, Jing Tian, Jisheng Zhang, Yong Wang, Wei Sun
    Chinese Chemical Letters. 2022, 33(3): 1515-1518.

    The enantioselective epoxidation of olefin by MnⅡ(R,R-PMCP)(OTf)2, H2O2 and H2SO4 was explored by DFT calculations and experiments. Theoretical results suggest that [MnⅤ(O)(R,R-PMCP)(SO4)]+ species with a triplet ground spin state serves as the active species for the olefin epoxidation. It can be generated by the H2SO4 assisted O-O heterolysis of MnⅢ(OOH) species. MnⅢ-persulfate is also involved in this system, but it cannot promote the olefin epoxidation directly, preferring instead to transform into MnⅤ(O). Actually, the asymmetric epoxidation reactions with H2O2/H2SO4 or Oxone provide similar enantioselectivity in the presence of manganese catalyst. These observations further support the transformation of MnⅢ-persulfate to MnⅤ(O) species.

  • Le Jia, Chao-Jun Li, Huiying Zeng
    Chinese Chemical Letters. 2022, 33(3): 1519-1523.

    Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and commercial chemicals. Up to now, the selective cleavage of C–O linkages of lignin to afford chemicals contains only C, H and O atoms. Our group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds. Herein, we present a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C–O bond cleavage for the preparation of benzyl amine compounds and phenols.

  • Li-Fei Tian, Ming Liu, Li-Xia Chen, Chao Huang, Qian-Jiang Zhu, Kai Chen, Jiang-Lin Zhao, Zhu Tao
    Chinese Chemical Letters. 2022, 33(3): 1524-1528.

    Since the outer surface interaction of Q[n]s (OSIQ, including self-, anion- and aromatic-induced OSIQs) was proposed in 2014, it has become the most important research area in our group to construct various Q[n]-based supramolecular frameworks via the OSIQ strategy. Herein, we report a novel supramolecular framework constructed using cucurbit[8]uril (Q[8]) and 4-sulfocalix[6]arene (SC[6]A). This Q[8]/SC[6]A-based supramolecular framework is a product via the perfect combination of self-, anion- and aromatic-induced OSIQs. This framework has the characteristics of easy preparation and high stability with the most important feature being the sequence selective capture of specific metal cations, such as common alkali- and alkaline earth metal ions, and renewability. Thus, this framework may be used in seawater desalination, potassium ion enrichment, radioactive cesium ion pollution source treatment, Gruinard's treatment or water softening and other applications.

  • Chun Liu, Yu Xia, Zhu Tao, Xin-Long Ni
    Chinese Chemical Letters. 2022, 33(3): 1529-1532.

    An approach for the construction of crystalline porous supramolecular organic frameworks (SOFs) via outer-surface interactions of cucurbit[6]uril (Q[6]) with high yield is presented. This approach enables the noncovalent integration of guest molecules into ordered topologies and creates new host–guest-complex-based SOFs; i.e., the topology can be predesigned and constructed by using [ZnCl4]2− anions to induce the formation of solid Q[6]-SOFs, and the pore wall surface can be easily modified by the Q[6]-encapsulated guest molecules. In addition, one of prepared solid Q[6]-SOFs showed a high drug-loading capacity and smart potential release control for drug-delivery applications

  • Zhanqi Cao, Dongpu Wu, Mengzhen Li, Fan Yang, Zhikai Li, Wankai An, Song Jiang, Xin Zheng, Caoyuan Niu, Dahui Qu
    Chinese Chemical Letters. 2022, 33(3): 1533-1536.

    The preparation of intelligent-responsive materials with controllable topology structure has long been a significant objective for chemists in the field of materials science. In this paper, we designed and prepared a linear-cyclic reversible topological structure polymer based on the bistable [1]rotaxane molecular shuttle. A ferrocene-functionalized [1]rotaxane and naphthalimide fluorophore group are introduced into the both ends of the polymer, which exhibit distance-induced photo-electron transfer effect. The structural transformation between linear and cyclic state of polymer is demonstrated by simple acid-base stimuli, accompanying visual fluorescence changes. The transformation process was characterized by 1H NMR spectra and fluorescence spectra. This work provides a novel strategy to construct functionalized polymers with topological structure.

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