Insulin is a commonly prescribed drug for the treatment of type I and type Ⅱ diabetes. As for the efficiency in controlling blood glucose level, insulin therapy is one of the most effective treatments for diabetes. The current administration route of insulin is mainly through subcutaneous injection, which leads to many undesirable side effects such as pain, local tissue necrosis or infection, and nerve damage. Recently, various closed-loop and smart insulin delivery systems have been developed based on the emerging nanotechnologies. Recent progress in the construction of closed-loop and smart insulin delivery system, which mainly focuses on the response mechanism, different strategies for fabricating the carrier matrix, and the regulation principle of the smart insulin release is described. Advantages and drawbacks of the current insulin delivery systems are also discussed, along with the opportunities and challenges in future.

Recently, the fluorescent bio-probe based on water-soluble boron-dipyrromethene (BODIPY) obtains enormous progress on structural optimization and functional modification, and becomes novel high-performance biological imaging materials owing to the development of hydrophilic modification. Focusing on the methods for improving the hydrophilicity of BODIPY, the water-soluble BODIPYs have been classified as ionic probe, electrically-neutral probe and amphiphilic probe. The research progress on the application of water-soluble BODIPY dyes in field of biology and medicine since 2006 has been summarized in this review, such as detection of necessary and pathogenicbiological chemical components, early detection and intervention of cancer, labelling drug delivery, marking specific organelles, real-time monitoring of biochemical and property changes with cells, andphotodynamic therapy. The merits of methods for improving the hydrophilicity and main issues of current studies have been summed up. The hypothesis for future directions has also been put forward.

Spiropyran compound is widely used as an important class of photochromic compounds. Three new types of 1, 8-naphthalimide compounds with spiropyran unit were synthesized and the structures were characterized. The photochromic characteristics research shows that their response time of the ring opening process is long even difficult to be detected comparing the classical spiropyran. And the reason of their prolonged ring opening reaction is analyzed theoretically and structurally. The photochromic properties of SP3 are more obvious both in solid medium and organic solvents due to the presence of the strong electro-withdraw substituent. It turned into orange red from yellow in polyethylene glycol (200) and from yellow to grey purple in acetone. The investigation of the UV-Vis absorption spectra also showed its negative solvent effect in different organic solvents. There is no significant difference in the absorption wavelength of the spiropyran unit ring opened after irradiation compared with the standard one. The fluorescence properties of the three compounds were investigated to find that SP1 and SP2 showed obvious fluorescence color changes prior and after the UV irradiation in the silica gel, and no fluorescence color changes were detected in polymethylmethacrylate (PMMA) and organic solvents. Fluorescence changes of compound SP3 in acetone were not detected after the UV irradiation. The compound SP3 emitted green fluorescence and became orange yellow fluorescence after ultrasonic irradiation in polyethylene glycol (200). The changing process was detected by fluorescence spectrum. The fluorescence color change of SP3 is more obvious in the thin layer silica gel before and after irradiation. As time elapses, the green fluorescence converted to red one and turned into red from orange yellow eventually. The fluorescence spectrum of the compounds in PMMA film showed that the compound SP3 played the role of a dual-color fluorescent molecular switch. Because of the amino-group in its molecular structure, this dual-color fluorescent molecular switch is suitable for application in labeling biological system.

Helicenes are a kind of π-conjugated helical compounds which are consisted of ortho-fused benzene or other aromatic rings. Compared to other kinds of chiral catalysts, studies on helicene-based catalysts with helical chirality showed late start and lagging development. However, since helicene molecules exhibit structural rigidity, thermal stability, easily functionalization, and excellent chiral environment for asymmetric catalysis by continuous elaborate curve in three-dimensional space, investigation on the synthesis of helicene-based chiral catalysts and their applications in asymmetric catalysis have attracted increasing interest in recent years. According to the different roles of the helicenes played in the asymmetric catalysis, the helicene-based catalysts can be classified into chiral inducers, helically chiral ligands and helical organocatalysts, and their applications in asymmetric catalysis will be focused on in this review, respectively.

Halogen ions play an important role in chemistry, biology and material. The concentration of fluoride in the organism directly affects its health. The halide materials often act as flame retardant to improve the ignition point for plastic and other polymer products. So it is of great significance to detect halogen ions. Chemosensors include colorimetric and fluorescent sensors, which have the advantages of good selectivity and high sensitivity. In recent years, some halogen ion chemosensors have been reported widely. According to the type of host and guest molecules, halgen ion chemosensors mainly include fluoride ion chemosensors, iodine ion chemosensors, dual channel chemosensors and functional chemosensors. In this paper, the progress of halogen ion chemosensors in recent years is reviewed, the synthetic strategies for them are summarized and the future research direction of halogen ion chemosensors is prospected.

Among the numerous bio-active species which are involved in the various chemical reactions in our body, reactive oxygen species (ROS) are a class of important biological species, which are oxidative. ROS can maintain the intracellular redox balance and are tightly related with the cell growth and death. Hence, the fluorescence detection of intracellular ROS has attracted wide attention. However, owining to the inherent features of ROS, such as the short lifetime and high reactivity, fluorescence analysis of ROS is always faced with some problems, like low selectivity and side reactions. Herein, the development of small molecular fluorescent probes for intracellular ROS over the past decade is summarized, and the design mechanisms and bio-applications of these probes are emphasized.

A novel CN^- chemosensor based N-4-pyridylcoumarin-3-carboxamide derivative Q1 was designed and synthesized. The recognition performance of sensor Q1 for ten different anions was studied by UV and fluorescence spectroscopy. When anions such as CN^-, F^-, Cl^-, Br^-, I^-, AcO^-, H₂PO₄^-,HSO₄^-,ClO₄^- and SCN^- were added to the mixed solution (DMSO/H₂O, V:V=9:1), addition of CN^- could increase the absorption peak of Q1 at 304 nm, and the corresponding fluorescence produced a strong emission peak at 431 nm. Q1 solution with CN^- emitted strong blue fluorescent that can be easily observed by naked eyes. The color changed (from colorless to faint yellow) and the "Turn-On" fluorescence behavior suggested that Q1 could detect CN^- by dual-channel. Happily, the fluorescent limit of detection (LOD) is 1.44×10^-8 mol/L, was lower than the specified content by World Health Organization (WHO) in drinking water. Based on all the experimental facts, we speculated that the possible identification mechanism was that the addition reaction took place between Q1 and CN^-, and it can also be confirmed by density functional theory (DFT). This result can be applied to the detection of CN^- in cherry kernel.

A turn-on probe, which exhibited highly selective and sensitive signaling behaviors toward Fe³⁺ over other common metal ions, has been synthesized and confirmed by ¹H NMR, ¹³C NMR, IR and MS. The addition of Fe³⁺ to the solution of probe induced a remarkable UV-Vis and fluorescence enhancement along with obvious color change detected by the naked eye. The reaction mechanism was also investigated and proposed as that the probe complexed Fe³⁺ via a 1:1 binding mode, and the subsequent complexation caused the ring-opening of the rhodamine spirolactam and thereby the changes of absorbance and fluorescence. These remarkable properties may allow Fe³⁺ to be detected directly in the presence of the other examined competing metal ions. Then, cells experiments showed that the probe could permeate through cell membranes and react to Fe³⁺ within living cells. Additionally, the probe was further used for detecting Fe³⁺ ions in living mouse which exhibited excellent fluorescence imaging.

Due to high selective coordination ability of phosphate anion to the Zn center of pincer type terpyridine zinc nitrate complexes, intriguing visual recognition of phosphate anion via selective metallo-hydrogel formation has been successfully realized. Based on this interesting result, a series of control experiments were conducted including the study on thermodynamic stability, rheological property and microscopic morphology of the metallo-hydrogel, a plausible mechanism of the discrimination was proposed.

Methods for optical detection or sensing of L-cysteine with high selectivity and sensitivity have attracted increasing interest recently due to the potential association of L-cysteine to the fields of pathophysiology and clinical medicine. Recent advances since 2010 on reaction-based small molecule sensors as well as sensing ensembles constructed by metal complex and nanomaterials for optical sensing of L-cysteine were highlighted. The future advances in this field were also predicted and given at the end of this review.

A novel rhodamine B Schiff-base fluorescence probe 1 was synthesized and characterized by ¹H NMR, ¹³C NMR, MS and single-crystal X-ray analysis. The recognition properties of the probe 1 with Hg²⁺ ions were investigated in ethanol-water (V/V=7/3, HEPES 10 mmol/L, pH=7.0) by the UV-Vis spectrophotometry and the fluorescence spectrophotometry. The probe 1 showed remarkable "turn-on" fluorescent responses to Hg²⁺ with good selectivity over the other metal ions examined. The 1:1 binding model of probe 1 with Hg²⁺ was established by Job's plot and MS spectra. The probe can be applied to the quantitative analysis of Hg²⁺ with a linear range covering from 0 to 50 μmol/L. The fluorescence imaging experiments in MGC-803 living cells demonstrated that 1 could be used in biological systems to monitor Hg²⁺.

Ethyl 5-phenyl-2-(3-(trifluoromethyl)phenyl)-2H-1,2,3-triazole-4-carboxylate (EPFC), a newly synthesized compound, is used to study its structural properties and explore as a fluorescent probe for metal ions. EPFC was investigated in terms of structural, fluorescence spectroscopic, UV-Vis spectroscopic and theoretical analysis by using HF/6-31G(d), CIS/6-31G(d) and B3LYP/6-31G(d) methods, respectively. The corresponding product was characterized by NMR and HRESIMS methods. The interactions of the compound with 15 kinds of metal ions (Pb²⁺, Mn²⁺, K⁺, Na⁺, Ag⁺, Ca²⁺, Cd²⁺, Co²⁺, Cu²⁺, Fe³⁺, Zn²⁺, Ni²⁺, Hg²⁺, Li⁺ and Mg²⁺) were investigated by UV absorption spectroscopy and fluorescence spectroscopy. The quantum chemical values suggested that it is easy for EPFC to lose electron with weak electron accepting ability by frontier molecular orbital analysis. The calculated spectra were complimented with experimental measurements in great degree. In addition, a novel rhodamine B derivative containing 1,2,3-triazole unit, and REPFC was successfully designed and synthesized by the reaction between rhodamine B and EPFC. REPFC displayed more selectivity response to Hg²⁺ ion than other metal ions in N,N-dimethylformamide (DMF)-H₂O (V/V=1/1, pH 7.4) within a REPFC concentration range of 2.67×10^-5~4.67×10^-5 mol·L^-1 with an fluorescent enhancement and a rapid chemical reaction. The triazole appended colorless chemosensor turns to pink upon complex formation only with Hg²⁺ions even in the presence of other common metal ions and enables naked-eye detection. The coordination mechanism and turn on/off fluorescence for Hg²⁺ ions were well proposed by explaining Hg²⁺ inducing the ring-opened rhodamine B moiety. This study was an advancement for the application of 1,2,3-triazole compound and provides guidance for using simple and high-selectivity Hg²⁺ probes in aqueous solutions under physiological conditions.

The detection and fluorescent identification of some substances such as sLea/x in vivo can provide important reference for the diagnosis, treatment and prognosis of disease, molecular tracing and further research on the mechanism of related diseases. Therefore, the development and discovery of high selectivity and high sensitivity chemsensors is of great value. Due to the special structure, phenyl boronic acid compounds could interact and bind with sugar, catecholamine containing catechol structure, fluoride or alkali cyanide. So boronic acids could be develeped as fluorescence sensors selectively for related substances, while have the advantages of high selectivity, high efficiency, rapid analysis and so on. In recent years, boronic acid has been functioned with new materials such as nanoparticles and quantum dots to design novel sensors for better performance. In this paper, the recent progress in the study of boronic acid compounds in sensors is reviewed.

Artificial foldamers were constructed by non-covalent interactions to mimic the structures of biomacromolecules, such as proteins and DNA, which is conducive to a better understanding of the chemical processes at the molecular level in nature. The significant advances in foldamers render it become one of the most important topics in supramolecular chemistry. Coordination bond is widely used in the self-assembly process due to its bond strength and diverse geometry. In this article, we summarize a few types of metal-coordination helical folding systems, including single helicate, double helicates, triple helicates, quadruple helicates and cyclic helicates, and their folding behaviors and structural reconfiguration in the coordination process.

Stimuli-responsive supramolecular drug delivery systems (SDDSs) self-assembled by supra-amphiphiles have received tremendous attentions in cancer therapy due to various advantages of SDDSs, such as enhanced drug bioavailability, prolonged blood circulation and retention time, improved drug stability and so on. The construction of smart supramolecular drug delivery systems based on the different structural characteristics of macrocyclic compounds are reviewed and their recent applications in anti-cancer drug delivery are described. Advantages and drawbacks of the current supramolecular drug delivery systems are also discussed, along with the opportunities and challenges in future.

With saddle-shaped cyclooctatetrathiophene (COTh) and 1, 3, 5-triazine as building blocks, three derivatives bearing one, two and three COTh units are synthesized via Kumada-typed reaction. Theoretical calculations indicate that the two absorption peaks in long wavelength region are derived from intramolecular charge transfer (CT) absorption. 2, 4- Di(methoxyl)-6-(5, 8, 11-tris(trimethylsilyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (1), 2-meth- oxyl-4, 6-di(5, 8, 11-tris(trimethyl-silyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (2) and 2, 4, 6-tris- (5, 8, 11-tris(trimethylsilyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (3) exhibit intramolecular charge transfer (ICT) state emission peaked in region of 560～570 nm in solution at room temperature, and give both local emission of COTh peaked at 400 nm and ICT state emission peaked in region of 480～500 nm in rigid solution at 77 K. In tetrahydrofuran (THF)-H₂O binary solvent system, compounds 1, 2 and 3 show typical aggregation induced emissions (AIE), which may be controlled by mechanism of restriction of intramolecular rotations (RIR) and restriction of intramolecular vibration (RIV). Crystal structure of 1 shows that intramolecular two rings of triazine and its linked thiophene are planar. There are strong C-C interactions between intermolecular rings of triazine and thiophene, which restrict the intramolecular rotation between triazine and thiophene rings. Such intermolecular C-C interactions are helpful to decrease the process of non-irradiative decay and increase AIE emission.

Fluorescent imaging technology has received great attention owing to their advantageous features in high sensitivity, relatively simple operations and real-time living cells, tissue and in vivo imaging. Compared with one-photon confocal imaging, two-photon confocal imaging offers considerable advantages such as high resolution, deep-tissue depth, lower tissue auto-fluorescence and so on. As typical D-π-A two-photon dyes, 1,8-naphthalimide dyes have wide application in two-photon imaging for enzyme, reactive carbon species, reactive oxygen species, reactive nitrogen species, biothiols and ions due to their advantages such as high photostability, large Stokes/anti-Stokes shifts. According to the mechanisms of intramolecular charge transfer, photoinduced electron transfer and fluorescence resonance energy transfer, etc., the application in two-photon imaging of 1,8-naphthalimide dyes is summarized and emphasized.

Triplet-triplet annihilation (TTA) upconversion, a unique technique that converting low-energy photons into higher-energy photons, has attracted much attention owing to its potential applications in various fields, such as solar cells, bioimaging, photocatalysis and photoelectric device. TTA upconversion has several advantages over other upconversion methods, such as allowing for the use of low excitation power density, readily tunable excitation/emission wavelength and high upconversion quantum yield. Both triplet-triplet energy transfer (TTET) and TTA processes in TTA upconversion follow the Dexter energy transfer mechanism. The components involved have to diffuse in the media and collide within the lifetime of their excited states to complete the energy transfer. Thus, most efficient TTA-based upconversion has been achieved with donor-acceptor pairs that are molecularly dissolved in deaerated organic solvents, which however significantly limited their practical applications. In recent years, more and more efforts have beendevoted to explore high-efficient TTA upconversion under aerated conditions by employing specific solid materials or viscous liquids as matrices to block oxygen. The recent advance of research of TTA upconversion in aggregated systems is summarized, including rubbery polymers, gels, molecular crystals, nanoparticles and supramolecular self-assemblies.

^aEngineering and Research Center for Southwest Bio-pharmaceutical Resources of National Education Ministry of China, Guizhou University, Guiyang 550025) (^bKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025) (^cCollege of Tobacco Science, Guizhou University, Guiyang 550025

A series of hexahydroquinazolin-2-amine-based derivatives have been designed and synthesized from renewable isolongifolanone. Their solid states exhibited an enhanced emission and a dark green to bright yellow color range. In addition to good thermal stability, their solid-state fluorescence is not readily restricted by multiple conventional factors such as long term UV irradiation, increasing operated pressure and elevated heating temperature. In contrast to the derivatives which undergo serious aggregation-caused quenching (ACQ), the dimethylamino-substituted derivative 1-6,6,10,10-tetramethyl-4-(4'-(N,N-dimethylamino)phenyl)-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanobenzo[h]quinazolin-2-imino)methyl)naphthalen-2-ol (3e) demonstrate obvious aggregation-induced emission (AIE) characteristics. Moreover, these fluorescent derivatives were also used for specific and sensitive sensing of Zn²⁺ ion in aqueous solutions. Then, their photophysical mechanisms were obtained by the density functional theory calculations. These probes were successfully applied to image Zn²⁺ ion in pollen grains of Althaea rosea.

Two fluorescent compounds, 7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid (3a) and 2,3-benzo[f]-7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid (3b) have been synthesized and characterized by the method of X-ray single crystal diffraction. 3a and 3b show high fluorescence quantum efficiency in both ethanol solution and solid state. In the crystal-state, dimerization of carboxylic group and intermolecular interaction lead to 3a owned a high fluorescence quantum efficiency (Ф_F=0.32). The dimers existing in 3a crystal lattice, are composed of carboxylic acid groups and have strong intermolecular interactions (bond lengths are 0.1870 nm, bond angles are 166.8°). All the atoms in dimer are nearly coplanar, showing extremely strong plane rigidity. The dimers are connected by C-H…O intermolecular hydrogen bonds, and the edge-to-face stackings exist in neighbor dimers.

The interaction of a pair of amino acid enantiomers, L-3-(2-naphthyl)-alanine (L-NA) and D-3-(2-naphthyl)-alanine (D-NA), with cucurbit[7]uril (Q[7]) and inverted cucurbit[7]uril (iQ[7]) was investigated, respectively, by using NMR spectroscopy, electronic absorption spectroscopy, fluorescence spectroscopies, isothermal titration calorimetry (ITC) experiments and MALDI-TOF mass spectrometry. Furthermore, the similarities and differences of the self-assembly patterns between the two kinds of cucurbituril with different cavity sizes and this pair of amino acid enantiomers were also researched. The results obtained from the experiment revealed that the naphthyl groups of amino acids were all entrapped in the cavity of the Q[n]s, whereas the other section of amino acids remained outside the portal and thus resulted in a more stable supramolecular self-assembly at a 1:1 ratio. Meanwhile, we found that the two different kinds of cucurbit[7]urils showed a slightly different selectivity for the L/D-NA chiral enantiomer.

A host-guest system was successfully constructed from dimethoxypillar[5]arene (DMP5) and six guest molecules benzoazolidazole (G2), benzimidazole (G3) and benzothiazole (G1, G4, G5 and G6) via host-guest interactions and characterized by various techniques, including HRMS and ¹H NMR spectra. The result shows that heterocyclic compound was threaded into the cavity of pillar[5]arene to obtain host-guest system between DMpillar[5]arene and benzazole, forming inclusion complexes. Interestingly, the corresponding guest containing benzazole formed a stable host-guest complex with the same host. Moreover, the addition of guest compounds led to the effective reinforcement of the fluorescence intensity compared with the original guest species and the host (DMP5) that giving an additional support for the host-guest interaction based supramolecular assembly nature of the present system.

It is well-known that cyanide anion (CN^-) is a hypertoxic anion, which can cause adverse effects in both environment and living beings. Thus, it is highly desirable to develop strategies for detecting cyanide, especially in aqueous medium and food. However, due to the short half-life of free cyanide, long analysis time and interference from other competitive anions are general challenges for accurate monitoring of cyanide. Taking advantage of the special nucleophilicity of cyanide, a new colorimetric and fluorescent sensor (Q1-2) was synthesized based on naphtho[2,1-b]furan-2-carbonyl chloride and 2-aminobenzimidazole which designed by tuning the intramolecular hydrogen bonding to affect the π-conjugated efficiency. Upon the addition of cyanide anion, the probe displayed a red-shift in absorption spectra and the fluorescence decreased immediately with the detection limit of 8.0769×10^-7 and 1.0510×10^-9 mol/L, respectively. Other anions gave nearly no interference. Furthermore, Q1-2 was successfully applied to the naked eye identification for cyanide in the visible light and under the UV lamp in food samples and silica gel plates.

A novel sensor molecule 2-hydroxyl-1-naldehyde-N-(4-aminophenyl)-1,8-naphthalimide (H1) based on functionalized naphthalimide Schiff Base derivative was synthesized. H1 was characterized by ¹H NMR, ¹³C NMR and HRMS. Furthermore, its fluorescence properties were studied in dimethyl sulfoxide (DMSO)/H₂O (V:V=7:3) solutions. Its maximum emission wavelength was 496 nm. The solution of H1 has yellow-green fluorescence under the UV lamp (365 nm). H1 showed fluorescence-colorimetric dual channel identification ability for Fe³⁺. With the addition of various metal ions into the H1 solution, only Fe³⁺ caused the fluorescence of the H1 quenching and the color disappeared. Other cations such as Ag⁺, Ca²⁺, Ba²⁺, Co²⁺, Ni²⁺, Cd²⁺, Pb²⁺, Zn²⁺, Cu²⁺, Mg²⁺ and Hg²⁺ could not induce similar response. The results of anti-disturbance experiment demonstrated that other cations can not interfere in the detection of Fe³⁺. H1 has good sensitivity for Fe³⁺, the fluorescence and UV-Vis detection limits of the H1 for Fe³⁺ are 3.04×10^-8 and 2.71×10^-6 mol·L^-1, respectively. Finally, the test strips based on the H1 were prepared, which could conveniently and efficiently detect Fe³⁺ in water.

Fluoride ion is an anion with the high electronegativity and the smallest radius. It has important application in all aspects of daily life. In this paper, based on the cleavage of Si-O bond induced by fluoride ions, a novel derivative of perylene B which contains four silicon oxygen bond was designed and synthesized, and this fluorescent chemosensor could recognize F^- with good selectivity and high sensitivity. The probe molecule had a fast response time for F^- and the sensing procedure could be completed in about 1 min, and the detection limit of F^- of the probe molecule B reached 3.5×10^-8 mol·L^-1.

A novel supramolecular host-guest complex of the anticancer drug capecitabine (CAP) with symmetrical α, α',δ, δ'-tetramethyl-cucurbit[6]uril (TMeQ[6]) has been characterized using nuclear magnetic resonance spectroscopy, MALDI-TOF mass spectrometry, isothermal titration calorimetryand fluorescence spectroscopy analyses. The result revealed that the alkyl chain of CAP is located inside the cavities of TMeQ[6], whereas the other part of CAP remains outside the portal. Our results suggest that TMeQ[6] could be a promising candidate for use as an excipient in the pharmaceutical and medical research ?elds.

The supramolecular functional system based on host-guet interaction between monosubstituted ferrocene derivatives and pillararene-based macromolecule molecules has made impressive progress in many different fields. The host-guet interaction between 1,1'-disubstituted ferrocene derivatives and water-soluble pillar[6]arene was preliminarily explored and studied. This work may give some support for the subsequent development of supramolecular functional systems, such as rotaxane, pseudorotaxane systems, based on the host-guet interaction between 1,1'-disubstituted ferrocene derivatives and water-soluble pillar[6]arene.

Long aromatic polymer chains which based on 3,5-diaminobenzoic acid derivatives and 4,6-dihydroxyisophthalic acid derivatives are designed and synthesized. The results of solubility, NMR, UV-Vis spectrum and circular dichroism (CD) experments indicate that the polymer adopts a hollow helical conformation that is stablized by intramolecular H-bonding interaction between side chains.

A novel fluorescent "turn-on" probe 7-(dibutylamino)-2'-((2-hydroxybenzylidene)amino)-3-methyl-1-phenyl-1H-spiro[chromeno[2,3-c]pyrazole-4,1'-isoindolin]-3'-one (SCPz-S) with Schiff base structure was designed and synthesized, and characterized by ¹H NMR, ¹³C NMR and high resolution mass spectrometry (HRMS). The UV-Vis and fluorescence spectra were used to investigate the ions recognition capability of probe SCPz-S. It was excavated that the probe SCPz-S has a dual colorimetric and fluorescence response to CN^- in THF/H₂O (V:V=1930:50, 5 mmol/L Tris-HCl, pH=7.4). After adding CN^-, the system of probe SCPz-S will change from colorless to yellow, and fluorescence enhance 1060-fold at 575 nm. The sensor SCPz-S also has good anti-interference ability and a wide pH range from 3 to 12 applicable. Its LOD for CN^- is 1.121×10^-8 mol/L, and the recognition mechanism has been investigated.

Supramolecular polymer can be formed from amphiphilic block copolymer polystyrene-b-poly(4-vinylpyridine) (PS-b-P4VP) and 4'-iodo-4-dimethylaminoazobenzene molecule through halogen bond. In this paper, honeycomb ordered porous films were prepared by static breath figure (BF) method by this supramolecular polymer. The effects of IAzo content and light illumination conditions on the morphology of supramolecular polymer porous film were studied in detail. The formation of the supramolecular polymer, the surface and the fracture morphology of the porous film were characterized by infrared spectroscopy and scanning electron microscopy. These results showed that with the increase of IAzo content, the pore size of supramolecular polymer porous film gradually increased. In addition, under the irradiation of linearly polarized light, the round hole structure of the porous film can be converted into rectangular holes or rhombic holes according to the change of polarization direction of linearly polarized light. The degree of deformation increases with the increase of azobenzene content and the extension of illumination time. The porous film prepared from this azobenzene-containing supramolecular polymer realizes the light regulation of porous structure by non-synthetic means.

Porous organic polymer fluorescence materials have the characteristics of high porosity and outstanding fluorescence properties. The function of fluorescence sensing is given when the skeleton has binding sites with specific analytes, such as nitroaromatic explosives (NAEs), metal ions, anions, gases, organic solvents, etc. In this paper, according to the different types of porous organic polymer materials (POPs), namely the amorphous porous organic polymer materials, crystal porous metal organic framework materials (MOFs) containing coordination bond, and crystal covalent organic framework materials (COFs), the new progress of the POPs fluorescence materials in recent years is reviewed. Especially, the design and synthesis based on functional organic molecules, and their fluorescence sensing applications, are introduced in details. In the future, continuing to design new types of fluorescent COFs from the molecular level is a development direction of highly efficient and recyclable fluorescence chemosensors for detecting NAEs, metal ions, anions, etc.

In recent years, designing and synthesizing fluorescent nanoprobes with good biocompatibility, stable optical properties and low cytotoxicity are research hotspots in the biomedical field. The novel tetraphenylethene-based fluorescent probe (TPE-Rho) was synthesized by reaction of 1,1,2-triphenyl-2-(4-formylphenyl)ethene with 2-(4-oxo-3-phenyl-1,3-thia-zol-2-ylidene)malononitrile. After the aggregation-induced emission (AIE) characteristics of TPE-Rho were investigated, TPE-Rho dots with uniform particle size distribution were obtained through a modified nanoprecipitation method by using Pluronic F-127 (amphiphilic surfactant) as the encapsulation. TPE-Rho dots have excellent optical property such as strong yellow fluorescence, good stability and long Stokes shift (ca. 200 nm), and have little effect on cell growth activity. Then, TPE-Rho dots were utilized to stain live SK-Hep1 cells and LoVo cells, the staining region and fluorescent intensity were analyzed. The experimental results show that TPE-Rho dots have no significant effect on cell viability, and can stain live cells and selectively act on the cytoplasm. Thus, it can be confirmed that TPE-Rho dots has good biocompatibility, low cytotoxicity, high cell membrane permeability, and good stability, therefore it can be used as a viable cell staining agent.

Pillararenes, a new kind of macrocyclic aromatic compounds, are closely attracted because it was used to construct supramolecular gels. In this paper, an iodine-functionalized pillar[5]arene was designed and synthesized. This pillar[5]arene can form a stable supramolecular organogel in cyclohexanol, and phase transition temperature is approximately 96 ℃. The formation process of the organogel was characterized by concentration dependent ¹H NMR spectrum, 2D NOESY experiment, X-ray diffraction (XRD) powder diffraction and scanning electron microscope. The experiment results showed that a sheet-like structure was formed in self-assembly process of iodine-functionalized pillar[5]arene. Meanwhile, the fluorescent recognition properties of organogel were studied. With the addition of 0.5 equiv. of various metal ions (Fe³⁺, Ag⁺, Ca²⁺, Co²⁺, Ni²⁺, Cd²⁺, Pb²⁺, Zn²⁺, Cu²⁺, Mg²⁺ and Hg²⁺) onto the organogel, Hg²⁺ and Ag⁺ can cause blue fluorescence quenching of the organogel after 10 min. Therefore, this gel can be used for fluorescent detection of Hg²⁺ and Ag⁺.

A functionalized porous organic polymer POP-BINOL has been prepared and characterized by various techniques including carbon-13 cross-polarization magic-angle spinning nuclear magnetic resonance (¹³C CP/MAS NMR), fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (pXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), nitrogen adsorption and thermogravimetric analysis (TG). After being treated with Ti (OⁱPr)₄, the composite material could be used as highly effective and reusable heterogeneous catalyst for asymmetric diethylzinc addition to aldehydes with medium and upper ee value.

Chiral compounds play an essential role in asymmetric synthesis, biology, medical field and pharmacology. It is necessary to establish fast, sensitive and high enantioselective chiral analysis methods. Chiral sensors, which could determine the absolute configuration and the value of enantiomeric excess of enantiomers, have the advantages of simple, rapid, sensitive and real-time. Herein, the review is focused on the recent progress of chiral fluorescent sensors, circular dichroism sensors, UV-Vis sensors, NMR sensors and MS sensors. Their characteristics, sensing mechanism and applications in chiral recognition are reviewed, and the prospects of chiral sensors are also discussed.

L-Cys-β-CD@AuNPs nanoparticles were synthesized by a simple method of the reduction of HAuCl₄ with NaBH₄and L-Cys-CD. The catalytic activity of L-Cys-β-CD@AuNPs nanoparticles for the catalytic reductions of 4-nitrophenol and 4-nitro-1-naphthol was researched in detail. Because of the selective binding of β-cyclodextrin (β-CD) to different guest molecules, L-Cys-β-CD@AuNPs exhibits diverse catalytic activities for different substrates. The experimental results prove that L-Cys-β-CD@AuNPs shows better catalytic efficiency for the reduction of 4-nitro-1-naphthol than p-nitrophenol.

A pharmaceutical intermediate, 3-pyridyl benzoxazole derivatives (DIHY), was designed and synthesized as the guest molecule. The self-assembly binding models of tetramethyl cucurbit[6] uril (TMeQ[6]), cucurbit[7] uril (Q[7]) and cucurbit[8] uril (Q[8]) with DIHY were investigated by ¹H NMR, MS, isothermal titration calorimetry and UV-Vis spectrum. The results showed that there are different modes of interaction between these three different cucurbit[n] uril and DIHY. For the TMeQ[6]-DIHY system, the guest molecule is located at the port of the TMeQ[6], while for the Q[7]-DIHY system, the 4,5-dihydro-2H-benzoxazole moiety of the guest molecule reside within the cavity of Q[7] host, whereas the pyridyl group of DIHY guest remains outside of the portal to form the 1:1 inclusion complexes of pseudorotaxane structure. Nevertheless, the 4,5-dihydro-2H-benzoxazole moiety of two guest molecule is included in the cavity of Q[8] host in a "face to face" stacking way, while the pyridine group of DIHY is located at the port of Q[8] to form a 1:2 supramolecular structure.

The endoplasmic reticulum, a subcellular organelle, plays an important role in the life activities of mammalian cells. Therefore, visualizing the endoplasmic reticulum, and further examining its active substances, microenvironments and physiological processes have important guiding value for the diagnosis and treatment of related diseases. In recent years, the design and synthesis of endoplasmic reticulum-targetable fluorescent probes have received more and more attentions. Currently, reported endoplasmic reticulum-targetable fluorescent probes mainly include simple endoplasmic reticulum imaging, metal ions, small molecule material, big molecule material, microenvironments, etc. This article summarizes and describes the design and synthesis of the reported endoplasmic reticulum-targetable fluorescent probes, analyzes the application of endoplasmic reticulum fluorescent probes in the study of cellular physiological processes, and prospects the development trend of endoplasmic reticulum-targetable fluorescent probes.

This review summarizes studies on halogen bonding of fluorine-containing alkyl and aryl iodides in China. From 1987 to 1993, Chen et al. found that there existed donor-acceptor interaction between fluorinated organic (di)iodides, as Lewis acids, and organic Lewis bases such as amines and ethers, which represented early important advances for the research on the non-covalent force currently called as halogen bonding. From 2001 to now, several groups have used halogen bonding as driving force to conduct researches on crystal engineering. In this catogery, Zhu et al. investigated the one-dimensional self-assembly between perfluoro-α,?-diioodalkanes and amines, ethers, and hexamethylphosphamide. Jin et al. studied the complexation between fluorinated aryl iodides and various N-heterocycles, whereas Zhang and Li et al. constructed supramolecular double and quadruple helices from one or two molecular components. Jin et al. conducted extensive studies on C—I…p halogen bonding and its applications in crystal engineering. Wang and Wan et al. utilized halogen bonding to induce trianglular aromatic molecules to co-assemble into two-dimensional honeycomb arrays on surface, whereas Wang et al. utilized halogen bond to induce mono-layer and layer-by-layer self-assembly of two polymers or organic molecules. Zhao and Li et al. developed the applications of halogen bonding in solution-phase multi-site molecular recognition of foldamer receptors for ICF₂-incorporated tri-armed guests. Hu, Gong, Liao et al. utilized halogen bonding to improve the material properties of a variety of organic aromatic molecules. Several groups have also used halogen bonding to increase the selectivity of a number of organic reactions. Representative examples are described, which highlight the utility of halogen bonding.