Single Bond Rotation Research Articles

Directional Bias in Molecular Photogearing Evidenced by LED‐Coupled Chiral Cryo‐HPLC

AbstractMolecular gearing systems are technomimetic nanoscale analogues to complex geared machinery in the macroscopic world. They are defined as systems incorporating intermeshed movable parts which perform correlated rotational motions by mechanical engagement. Only recently, new methods to actively drive molecular gearing motions instead of relying on passive thermal activation have been developed. Further progress in this endeavor will pave the way for unidirectional molecular gearing devices with a distinct type of molecular machine awaiting its realization. Within this work an essential step towards this goal is achieved by evidencing directional biases for the light‐induced rotations in our molecular photogear system. Using a custom‐designed LED‐coupled chiral cryo‐HPLC setup for the in situ irradiation of enantiomeric analytes, an intrinsic selectivity for clockwise or counterclockwise rotations was elucidated experimentally. Significant directional biases in the photogearing processes and light‐induced single bond rotations (SBRs) are observed for our photogear with directional preferences of up to 4.8 : 1. Harnessing these effects will allow to rationally design and construct a fully directional molecular gearing motor in the future.

Directional Bias in Molecular Photogearing Evidenced by LED-Coupled Chiral Cryo-HPLC.

Molecular gearing systems are technomimetic nanoscale analogues to complex geared machinery in the macroscopic world. They are defined as systems incorporating intermeshed movable parts which perform correlated rotational motions by mechanical engagement. Only recently, new methods to actively drive molecular gearing motions instead of relying on passive thermal activation have been developed. Further progress in this endeavor will pave the way for unidirectional molecular gearing devices with a distinct type of molecular machine awaiting its realization. Within this work an essential step towards this goal is achieved by evidencing directional biases for the light-induced rotations in our molecular photogear system. Using a custom-designed LED-coupled chiral cryo-HPLC setup for the in situ irradiation of enantiomeric analytes, an intrinsic selectivity for clockwise or counterclockwise rotations was elucidated experimentally. Significant directional biases in the photogearing processes and light-induced single bond rotations (SBRs) are observed for our photogear with directional preferences of up to 4.8 : 1. Harnessing these effects will allow to rationally design and construct a fully directional molecular gearing motor in the future.

Controlled interconversion of macrocyclic atropisomers via defined intermediates

Macrocyclic conformations play a crucial role in regulating their properties. Our understanding of the determinants to control macrocyclic conformation interconversion is still in its infancy. Here we present a macrocycle, octamethyl cyclo[4](1,3-(4,6)-dimethylbenzene)[4]((4,6-benzene)(1,3-dicarboxylate) (OC-4), that can exist at 298 K as two stable atropisomers with C2v and C4v symmetry denoted as C2v-OC-4 and C4v-OC-4, respectively. Heating induces the efficient stepwise conversion of C2v- to C4v-OC-4 via a Cs-symmetric intermediate (Cs-OC-4). It differs from the typical transition state-mediated processes of simple C–C single bond rotations. Hydrolysis and further esterification with a countercation dependence promote the generation of C2v- and Cs-OC-4 from C4v-OC-4. In contrast to C2v-OC-4, C4v-OC-4 can bind linear guests to form pseudo-rotaxans, or bind C60 or C70 efficiently. The present study highlights the differences in recognition behavior that can result from conformational interconversion, as well as providing insights into the basic parameters that govern coupled molecular rotations.

A thiol-anchored solvatochromic and fluorogenic molecular rotor for covalent protein labeling in SDS-PAGE and mitochondria specific fluorescence imaging.

Fluorescent labeling is a widely used method for protein detection and fluorescence imaging. A solvatochromic and fluorogenic molecular rotor DASPBCl was developed for covalent protein labeling in solution and SDS-PAGE, and also for stable mitochondria labeling and fluorescence imaging. The dye DASPBCl consisted of a 4-(N,N-dimethylamino)phenyl moiety as the electron donor and a positively charged N-benzylpyridinium moiety as the electron acceptor. A benzyl chloride group was introduced into the pyridine moiety for covalent labeling of thiol in proteins. When the fluorescent dye DASPBCl is covalently labeled to the thiol of proteins, significantly enhanced fluorescence was obtained, which is attributed to the polarity sensitivity caused solvatochromic effect from the hydrophobic protein structure and the viscosity sensitivity caused fluorogenic effect from the restriction of single bond rotation. DASPBCl exhibits high sensitivity and good linear response for protein detection in SDS-PAGE analysis with both the pre-staining method and post-staining method. DASPBCl was also successfully used for covalently protein-anchored fluorescence imaging of mitochondria in living cells.

Isomerization Pathways of a Mismatched Base Pair of A:8OG in Free Duplex DNA.

The A:8OG base pair (bp) is the outcome of DNA replication of the mismatched C:8OG bp. A high A:8OG bp population increases the C/G to A/T transversion mutation, which is responsible for various diseases. MutY is an important enzyme in the error-proof cycle and reverts A:8OG to C:8OG bp by cleaving adenine from the A:8OG bp. Several X-ray crystallography studies have determined the structure of MutY during the lesion scanning and lesion recognition stages. Interestingly, glycosidic bond (χ) angles of A:8OG bp in those two lesion recognition structures were found to differ, which implies that χ-torsion isomerization should occur during the lesion recognition process. In this study, as a first step to understanding this isomerization process, we characterized the intrinsic dynamic features of A:8OG in free DNAs by a free energy landscape simulation at the all-atom level. In this study, four isomerization states were assigned in the order of abundance: Aanti:8OGsyn > Aanti:8OGanti > Asyn:8OGanti ≈ Asyn:8OGsyn. Of these bp states, only 8OG in Asyn:8OGanti was located in the extrahelical space, whereas the purine bases (A and 8OG) in the other bp states remained inside the DNA helix. Also, free energy landscapes showed that the isomerization processes connecting these four bp states proceeded mostly in the intrahelical space via successive single glycosidic bond rotations of either A or 8OG.

Conformers influence on UV-absorbance of avobenzone

Avobenzone is most commonly used FDA approved chemical UV-A filter in many sunscreen formulations. An important drawback of avobenzone is its photounstability and undergoes chemical transformation upon exposure to UV-radiation/sunlight. Eventhough single bond rotations are implicated in the radiation induced chemical modification of avobenzone, the conformers role of avobenzone on UV absorbance is yet to be addressed. Using the In silico platform working on Density Functional Theory (DFT), the communication evaluates the role of conformers on UV absorbance spectra of enol/keto forms of avobenzone. The results indicate that the conformers of enolic-form of avobenzone have broad range of absorbance from 273-389 nm and the keto-form has relatively narrow range of absorbance from 266-288 nm. The chelated conformers of enolic-avobenzone with intramolecular hydrogen bond are swingy in nature yet possessing strong bond contributing to its broad-spectrum UVA filtering activity. Among the conformers of keto-form of avobenzone, the planar conformer with the torsional angle 180° undergo facile Norrish Type-I cleavage. Mapping of the data with previous experimental results has allowed identifying 3D structures involved in the key steps of photoketonization process of avobenzone. The reported results may help to understand the molecular basis of enol-to-keto photochemical transformation of avobenzone and to develop photostabilizer to endure long-lasting photoprotection to avobenzone.

Dissecting lysosomal viscosity fluctuations in live cells and liver tissues with an ingenious NIR fluorescent probe

Viscosity is a pivotal component in the cell microenvironment, while lysosomal viscosity fluctuation is associated with various human diseases, such as tumors and liver diseases. Herein, a near-infrared fluorescent probe (BIMM) based on merocyanine dyes was designed and synthesized for detecting lysosomal viscosity in live cells and liver tissue. The increase in viscosity restricts the free rotation of single bonds, leading to enhanced fluorescence intensity. BIMM exhibits high sensitivity and good selectivity, and is applicable to a wide pH range. BIMM has near-infrared emission, and the fluorescent intensity shows an excellent linear relationship with viscosity. Furthermore, BIMM possessing excellent lysosomes-targeting ability, and can monitor viscosity changes in live cells stimulated by dexamethasone, lipopolysaccharide (LPS), and nigericin, and differentiate between cancer cells and normal cells. Noticeably, BIMM can accurately analyze viscosity changes in various liver disease models with HepG2 cells, and is successfully utilized to visualize variations in viscosity on APAP-induced liver injury. All the results demonstrated that BIMM is a powerful wash-free tool to monitor the viscosity fluctuations in living systems.

Conformational Studies of β-Azapeptoid Foldamers: A New Class of Peptidomimetics with Confined Dihedrals.

Controlling amide bond geometries and the secondary structures of β-peptoids is a challenging task as they contain several rotatable single bonds in their backbone. Herein, we describe the synthesis and conformational properties of novel "β-azapeptoids" with confined dihedrals. We discuss how the acylhydrazide sidechains in these molecules enforce trans amide geometries (ω ~180°) via steric and stereoelectronic effects. We also show that the Θ(Cα -Cβ ) and Ψ(OC-Cα ) backbone torsions of β-azapeptoids occupy a narrow range (170-180°) that can be rationalized by the staggered conformational preference of the backbone methylene carbons and a novel backbone nO →σ*Cβ-N interaction discovered in this study. However, the ϕ (Cβ -N) torsion remains freely rotatable and, depending on ϕ, the sidechains can be parallel, perpendicular, and anti-parallel relative to each other. In fact, we observed parallel and perpendicular relative orientations of sidechains in the crystal geometries of β-azapeptoid dimers. We show that ϕ of β-azapeptoids can be controlled by incorporating a bulky substituent at the backbone β-carbon, which could provide complete control over all the backbone dihedrals. Finally, we show that the ϕ and Ψ dihedrals of β-azapeptoids resemble that of a PPII helix and they retain PPII structure when incorporated in Host-guest proline peptides.

Theoretical perspective for structural isomerism effect on photoelectric properties of organic room temperature phosphorescence molecules

Purely organic room temperature phosphorescence (RTP) materials have garnered extensive attentions in anti-counterfeiting and encryption, information display, biological imaging and organic light emitting diodes (OLEDs) due to the features of long lifetimes, low toxicity and good biocompatibility. Nevertheless, both the species and amounts of the efficient RTP molecules are far from meeting the requirements for practical applications, and the quantitative relationship between molecular structures and optoelectronic properties needs full elucidated. Herein, the photophysical properties and properties of three isomers (o-BA, m-BA and p-BA) are explored based on the first-principles calculations coupled with thermal vibration correlation function (TVCF) method and kinetic Monte Carlo simulations. The substituent effects on the molecular structures, intermolecular interactions, transition properties, Huang-Rhys factors and reorganization energies, excited state dynamics as well as transfer integrals and charge carrier mobilities are investigated in detail to clarify the structure-property relationships. Results show that o-BA achieves fast radiative rate on account of impressive transition dipole moment and oscillator strength, but equally large non-radiative decay rate leads to low RTP efficiency. Promisingly, the highest holes mobility is determined for o-BA due to the largest transfer integrals of holes originating from the strong intermolecular interactions. In addition, compared with o-BA and p-BA, m-BA could achieve fast intersystem crossing (ISC) rate with large spin orbit coupling constant and low non-radiative decay rate with small geometric structure changes. Relatively balanced holes and electrons mobilities of m-BA have been demonstrated, which contributes to the recombination of excitons and the improvement of luminescence efficiency. For p-BA, the strong intermolecular hydrogen bonding restricts the free rotation of single bonds and promotes the molecular coplanarity, which contributes to efficient emission. Furthermore, the charge mobility is calculated and the temperature dependence is investigated, the hopping mechanisms for studied isomers are illustrated. This work reveals the relationship among molecular structures, crystal packing modes, photophysical properties and charge transport properties of isomers, and provides an insight for molecular design and property prediction.

Theoretical studies on the photo protective mechanism of curcuminoids

In this work, the deactivation pathways of curcuminoids after photoexcitation was studied by employing density functional theory to explore their UVA radiation screening capacity. A comprehensive computational characterization of the excited-state processes of curcumin, demethoxycurcumin, and bis-demethoxycurcumin was done. The molecules exist in diketo and enol forms which are in equilibrium and interconvertible through keto-enol tautomerism. The enolic forms of each of the studied molecules have eight geometric cis–trans isomers as a result of torsion rotation about three different carbon–carbon double bonds across the aliphatic chain. For each geometric isomer, sixteen possible rotamers are found to exist due to rotation about five different carbon–carbon single bond rotations, also across the skeleton of the aliphatic chain. Upon photoexcitation, the studied molecules follow three main pathways of radiationless decay: (a) rotamerism and interconversion between rotamers of comparable energies which are in equilibrium, (b) interconversion between the cis–trans geometrical isomers where an efficient vibrational relaxation path is formed at ∼90° during torsion rotation about carbon–carbon double bond, and (c) excited state intramolecular proton transfer in a single O–H stretching vibration through a cyclic intramolecular hydrogen bonded ring formed at the centre of the molecule giving back the original structure. The absorption and emission spectra of the molecules were also simulated where the theoretically obtained absorption and emission maxima are close to the reported experimental values.

A coumarin hydrazone appended rotatable phenolic scaffold as fluorescent chemosensor for Ag+ ions and its bio imaging applications

A coumarin hydrazone-phenol conjugate, COH4 was designed, synthesized and utilized for the cation sensing studies by fluorimetry studies. The synthesized chemosensor was completely characterized by the usual spectroscopic and analytical studies. The COH4 receptor was examined for the detection of metal ions, in which it had a noticeable blue shifted fluorescence enhancement for Ag+ ions. Upon binding towards Ag+ ions, the photoinduced electron transfer (PET) process is inhibited via intramolecular charge transfer (ICT) process assisted by the arrest of the carbon–carbon single bond rotation. The binding stoichiometry of COH4 + Ag+ complexation ratio is noted to be 1:2, which was further confirmed by jobs plot method. The limit of detection (LOD) and limit of quantification (LOQ) were found to be 0.41 µM and 0.13 µM respectively. Moreover, COH4 was successfully utilized for the practical applications of Ag+ ion detection in bacterial cell lines.

Solvent-activated fluorescent Eu(III) complex with carbazole-benzene-tripyridine D-π-A system for rapid identification of specific alcohols

In this work, we prepared a Carbazole-Benzene-Tripyridine ligand with a d-π-A structure and synthesized its corresponding Eu (III) and Tb (III) complexes. The structures of the complexes were analyzed by single crystal X-ray diffraction. It was surprisingly that the fluorescence emission intensity of the Eu(III) complex increases significantly once the solvent was added, indicating that the fluorescence could be activated by the solvent. However, it was confirmed that in the solid state, the complex molecules in the lattice were orderly arranged and there was a π-π stacking effect. The π-π stacking caused strong intermolecular interactions leading to emission quenching. The addition of solvent broke the π-π stacking and enhanced the fluorescence of the Eu(III) complex. The color of the fluorescence emission of the Eu(III) complex depended on the kind of added solvent. The results of nuclear magnetic resonance (NMR) and density functional theory (DFT) calculations suggested that the rotation of the CC single bond in the d-π-A structure ligand in different solvents caused a change in the spatial angle between the carbazole-benzene unit and the tripolypyridine unit in the ligand, thereby changing the excited state energy of the ligand. Hence, the varied emission colors of the complex reflect differences in the energy transfer efficiency of the ligand to rare earth ion. The solvent effect of the Eu(III) complex was then successfully applied in the rapid identification of specific alcohols.

Nonaxisymmetrical 9,10-diarylanthracenes: Separable swivel conformers and promising optoelectronic properties

The chemical and physical functions of organic molecules are closely related to their conformations in both solutions and solid states, but the successful separation of organic conformers is usually very difficult because of the rapid internal rotation of single bonds. In the current work, we first demonstrate two stable and separable conformers with swivel cross-conjugated configuration based on 9,10-diphenylanthracene derivatives, and they are confirmed by 1H NMR spectra and single crystal analysis. The introduction of two bulky groups at the ortho positions of the two phenyls can enhance the internal rotation barrier of phenyl–anthryl single bond to fully stabilize the conformers in respective conformation even in reflux toluene. We find that they show similar solution but very different solid-state optical properties such as different emission wavelength and fluorescence efficiency. Moreover, only the syn conformer crystal can exhibit mechanochromic luminescence and mechanoluminescence.

Influence of the Steric/Electronic Properties of N-Aryl Substituents in Cycloplatinated Guanidinate(1−) Complexes on the Formation of Discrete Pt → Ag Complexes and One-Dimensional Coordination Polymer

The reactions of cycloplatinated guanidinate(1-) complexes 1-6 with AgTFA (TFA = OC(O)CF3) in 1:1 and 1:2 PtII/AgI molar ratios afforded complexes containing three types of Pt2Ag2 skeletons (7-10, 11, and 13), one 1D CP containing Pt2Ag3 skeleton (16), and a Pt2Ag4 complex (17) in 91-95% (method 1), 73-82% (method 2) (7-10), and 54-79% (11, 13, 16, and 17) yields. The reactions of 11 with 2,6-XylNC (2,6-Xyl = 2,6-Me2C6H3) and 4-DMAP (4-dimethylaminopyridine) gave a neutral complex 18 and an ionic complex 19, respectively. Molecular structures of 12 complexes were unambiguously determined by single-crystal X-ray diffraction. Ten complexes contain unprecedented PtAg skeletons and are shown to contain multiple number of dative Pt → Ag bonds supported by the TFA ligand, platinated carbon of the TAG ligand, or both these ligands in conjunction with the Ag-Ag contacts stabilized by argentophilic interaction. Further, the new complexes were characterized by analytical, IR, and multinuclear NMR (19F, 1H, 13C{1H}, and 195Pt) spectroscopies, powder X-ray diffraction, and TGA/DTA. In solution, 9 and 19 exist in more than one form as identified by multinuclear NMR, and this behavior is ascribed to the restricted (N2)C-N(H)Ar single-bond rotation of the TAG ligand. The photophysical properties of 9 and 11 are reported.

Novel 4,4′-Binaphthalimidyl derivatives with carboxyalkyl side chains: Synthesis, Aggregation-induced emission, Hydrogel and Cell imaging

The introduction of aryl groups and/or alkyl side chains to the periphery of a conjugated skeleton can modulate the pattern of molecular aggregation in solution and facilitate its aggregation-induced emission (AIE) performance. In this study, novel three compounds of 4,4′-binaphthalimidyl derivatives (BNICn) were synthesized successfully in which two 1,8-naphthalimide (NI) units were connected by a rotatable single bond at their 4-sites, and two carboxyalkyl chains (number of carbon atoms in the carboxyalkyl chains (n) = 2, 6, and 11) were linked with the nitrogen atoms of NI. BNICn has weakly fluorescent in dilute solutions but become highly emissive in aggregate states. Interestingly, they exhibited carboxyalkyl-dependent AIE properties. The AIE performance of BNIC2 with the shortest carboxyalkyl chain is the strongest among those of the three compounds. The aggregation was also confirmed by the dynamic light scattering (DLS) tests. Moreover, the fluorescence intensities enhanced with the increasing viscosity of the solutions, verifying that the restriction of intramolecular motions (RIM) leads to the occurrence of AIE. Furthermore, the interactions such as π-π stacking of NI groups, and the intermolecular hydrogen-bonding of the carboxyl groups at the terminal of the side chains of BNICn was respectively verified by 1H NMR and FTIR. Thus, a possible self-assemble mode of BNICn is that the stacking NI segments of BNICn are located by the intermolecular hydrogen bonds of carboxyl groups at the terminal of the side chains of BNICn enacting an anchor-like role during aggregation process. For BNIC2 with carboxymethyl group, the shortest spacer of methylene group resulted in more effectively restriction for the intramolecular vibration and rotation, leading to a more efficient AIE performance. Meanwhile, BNIC11 can form thermal-reversible fluorescence hydrogel with ethylenediamine as well as BNIC2 can be applied in cellular imaging. Thus, an effective strategy to achieve and adjust the AIE performance of NI derivatives is proposed.

In-situ gastritis diagnosis by an oral-administration NIR fluorescent probe with a large Stokes shift and high signal-to-noise ratio

Gastritis is one of the most common digestive disorders and affecting millions of people worldwide. Recent investigations discovered that abnormal viscosity changes in organisms are associated with an increasing number of diseases that cannot be cured or managed. However, the relationship between gastritis and viscosity has not been explored so far due to lacking the suitable tools for in situ detecting the variations of viscosity in stomach. Herein, we developed a new oral-administration fluorescent probe (NS-V) for in situ elucidation of gastritis viscosity variations, for the first time. Based on the TICT mechanism, the probe employs naphthalene as the fluorescence platform, the rotatable single bond as the viscosity sensitive site, N, N-dimethyl as the strong electron donating moiety and the pyridine salt as the strong withdrawing group to enlarge the π-conjugated system to prolong the emission wavelength. Interestingly, NS-V revealed a good fluorescence response for viscosity at the NIR region from a silent “off” state to “on” and demonstrated high sensitivity, large Stokes shift (262 nm in MeCN), and high signal-to-noise ratio. In addition, NS-V could elucidate the altered mitochondrial viscosity in inflammatory cells. More importantly, utilizing these satisfactory features of NS-V, we discovered a significant increase in viscosity in the gastritis mice. Notably, with the assistance of the oral fluorescence molecule, in vivo and in situ visualizing for the first time revealed the positive correlation between viscosity and gastritis. This work provides an important basis for the diagnosis of gastritis and the robust probe developed in this work possesses a potential application in diagnosis of gastritis without any pain.

A Quantum Mechanics-Based Method to Predict Intramolecular Hydrogen Bond Formation Reflecting P-glycoprotein Recognition.

Passive membrane permeability and an active transport process are key determinants for penetrating the blood-brain barrier. P-glycoprotein (P-gp), a well-known transporter, serves as the primary gatekeeper, having broad substrate specificity. A strategy to increase passive permeability and impair P-gp recognition is intramolecular hydrogen bonding (IMHB). 3 is a potent brain penetrant BACE1 inhibitor with high permeability and low P-gp recognition, although slight modifications to its tail amide group significantly affect P-gp efflux. We hypothesized that the difference in the propensity to form IMHB could impact P-gp recognition. Single-bond rotation at the tail group enables both IMHB forming and unforming conformations. We developed a quantum-mechanics-based method to predict IMHB formation ratios (IMHBRs). In a given data set, IMHBRs accounted for the corresponding temperature coefficients measured in NMR experiments, correlating with P-gp efflux ratios. Furthermore, the method was applied in hNK2 receptor antagonists, demonstrating that the IMHBR could be applied to other drug targets involving IMHB.

A near-infrared fluorescent probe for monitoring abnormal mitochondrial viscosity in cancer and fatty-liver mice model

Viscosity is an important component of cell microenvironment, and abnormal mitochondrial viscosity is associated with many diseases such as tumor and fatty liver. Herein, a near-infrared fluorescence probe (QX-V) based on quinoline-xanthene dye for detecting viscosity is constructed. In high viscosity medium, the free rotation of single bond is inhibited and the fluorescence is released. The probe shows high sensitivity together with good selectivity. Notably, QX-V has a long excitation wavelength (710 nm) and emission wavelength (786 nm). At the same time, the probe is a positively charged molecule that can target mitochondria. QX-V can not only distinguish cancer cells from normal cells, but also make a distinction between normal cells and fatty hepatocytes. In addition, QX-V is used to image viscosity abnormality in tumor-bearing mice. The probe also has a good ability to image viscosity abnormality caused by liver injury in fatty-liver mice.

Cinnamaldehyde‐based Natural Product as Viscosity‐Sensitive Sensor toward Liquid Safety Inspection

AbstractLiquids spoiled is considered gradually as a serious public problem, and heavily medical burden has been caused by this. We suspected that the viscosity level in the deterioration process is higher than those in the normal ones. For this reason, we have presented promising sustainable natural product, 4‐(dimethylamino)cinnamaldehyde (DLCA), for monitoring micro‐environmental viscosity alterations to achieve liquid safety inspection in a high sensitivity, rapid detection, and cheap equipment dependence pathway. This natural sensor with large stokes shift of 106.8 nm and maximum emission wavelength of 486.0 nm with high signal‐to‐noise ratio intensity. DLCA is consisted of a typical dimethylamine donor and aromatic aldehyde acceptor, connected with a rotatable single and double conjugated bond. The fluorescence intensity of this natural sensor increased 70 times with the enhancement of viscosity. The interference of other microenvironments such as pH and polarity, various potential analytes can be reduced. With the assistance of the fluorescence imaging technique, DLCA could sensitively and selectively non‐invasively identify thickening efficiency of various thickeners. Furthermore, DLCA may provide an attractive way to evaluate liquid deterioration extent with viscosity as a robust marker. We expected that this unique strategy will accelerate the efficient utilization of clean and reproducible resources.

Pillar[5]arenes modified tetraphenylethylene as fluorescent chemosensor for paraquat detection

Pesticide pollution has become a severe challenge for harming food quality and human safety. Therefore, it’s urgent to develop sensitive methods to detect and analyse pesticides. Herein, we successfully developed a new turn-on fluorescent chemosensor ( TPE-4P ), a tetraphenyl ethylene derivative modified with four pillar[5]arenes, which could sensitively, selectively, and rapidly detect the pesticide paraquat. In our study, we took full advantage of both the host-guest strategy and aggregation-induced emission (AIE) to achieve fluorescent enhancement of the chemosensor for paraquat, in which four pillar[5]arenes as the recognition units can selectively capture paraquat. The formation of the supramolecular complexes based on the interlaced host-guest interactions effectively restricted the intramolecular single-bond rotation and skeletal vibration, resulting in the intensive fluorescent emission. The detection limit for paraquat was low enough to reach 154.1 nM, and the detection time was short enough to meet the rapid detection conditions. Moreover, the test strips loaded- TPE-4P facilitated the detection process and achieved the semi-quantitative analysis for paraquat in real spiked samples. In addition, TPE-4P could respond to paraquat in living zebrafish obviously. These results suggest that the cooperation of host-guest and AIE chemistry could become useful for the design to detect some appropriate organic molecules. • A turn-on chemosensor was synthesized based on TPE and pillar[5]arene. • The sensor can rapidly, selectively, and sensitively detect pesticide paraquat through host-guest and AIE chemistry. • The sensor can be used in visual determination of paraquat in real samples and zebra fish. • The fabricated test strips can quantitatively detect paraquat. • The cooperation of host-guest and AIE chemistry is useful for the design of chemosensors.