Bis-Pyridine-Based Organogel with AIE Effect and Sensing Performance towards Hg2+

A novel gelator (1) based on a bis-pyridine derivative was designed and synthesized, which could form stable gels in methanol, ethanol, acetonitrile, ethyl acetate, DMF/H2O (4/1, v/v) and DMSO/H2O (4/1, v/v). The self-assembly process of gelator 1 was studied by field emission scanning electron microscopy (FESEM), UV–vis absorption spectroscopy, fluorescence emission spectroscopy, Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction and a water contact angle experiment. Gelator 1 exhibited obvious AIE behavior. On the base of its AIE, the gel of 1 could detect Hg2+, which resulted in fluorescence quenching and a gel–sol transition. 1H NMR titration experiments with Hg2+ revealed that the metal coordination interaction induced the fluorescence quenching and the breakdown of the noncovalent interaction in the gel system. This research provides a new molecular mode for designing a functional self-assembly gel system.

[1]  Sameer Hussain,et al.  AIE based luminescent porous materials as cutting-edge tool for environmental monitoring: State of the art advances and perspectives , 2022, Coordination Chemistry Reviews.

[2]  U. Manna,et al.  Role of chemistry in bio-inspired liquid wettability. , 2022, Chemical Society reviews.

[3]  Tao Chen,et al.  Recent Progress in Smart Polymeric Gel‐Based Information Storage for Anti‐Counterfeiting , 2022, Advanced materials.

[4]  Aiping Gao,et al.  Bis-naphthalimide-based supramolecular self-assembly system for selective and colorimetric detection of oxalyl chloride and phosgene in solution and gas phase , 2022, Chinese Chemical Letters.

[5]  Martin J. Sweetman,et al.  Metal ion sensing with graphene quantum dots: detection of harmful contaminants and biorelevant species. , 2022, Journal of materials chemistry. B.

[6]  A. Bianco,et al.  Self-assembly of amphiphilic amino acid derivatives for biomedical applications. , 2022, Chemical Society reviews.

[7]  Li Dang,et al.  Highly selective synthesis and near-infrared photothermal conversion of metalla-Borromean ring and [2]catenane assemblies , 2022, Chemical science.

[8]  Dian Niu,et al.  Double helical π-aggregate nanoarchitectonics for amplified circularly polarized luminescence , 2022, Nature communications.

[9]  J. Ying,et al.  Acid-Resistant and Physiological pH-Responsive DNA Hydrogel Composed of A-Motif and i-Motif toward Oral Insulin Delivery. , 2022, Journal of the American Chemical Society.

[10]  Qiu Yang,et al.  Mechanochemical transformation of fluorescent hydrogel based on dynamic lanthanide-terpyridine coordination , 2022, Chinese Chemical Letters.

[11]  R. E. Neisiany,et al.  Biodegradable Elastomers and Gels for Elastic Electronics , 2022, Advanced science.

[12]  Huey Wen Ooi,et al.  Desymmetrization via Activated Esters Enables Rapid Synthesis of Multifunctional Benzene-1,3,5-tricarboxamides and Creation of Supramolecular Hydrogelators , 2022, Journal of the American Chemical Society.

[13]  T. Tu,et al.  ATP-Induced Emergent Circularly Polarized Luminescence and Encryption. , 2022, Angewandte Chemie.

[14]  T. Maji,et al.  Visible Light Driven Photocatalytic CO2 Reduction to CO/CH4 using Metal-Organic 'Soft' Coordination Polymer Gel. , 2022, Angewandte Chemie.

[15]  Shaohua Zhang,et al.  Hydrogels for Underwater Adhesion: Adhesion Mechanism, Design Strategies and Applications , 2022, Journal of Materials Chemistry A.

[16]  Shaojie Men,et al.  A highly sensitive and ultra-stretchable zwitterionic liquid hydrogel-based sensor as anti-freezing ionic skin , 2022, Journal of Materials Chemistry A.

[17]  Xiao‐Qiao Xie,et al.  Programmable Transient Supramolecular Chiral G‐quadruplex Hydrogels via a Chemically Fueled Non‐Equilibrium Self‐assembly Strategy , 2021, Angewandte Chemie.

[18]  Xianhui Chen,et al.  Building Multi-color Emitters with Tailored Lanthanide-based Supramolecular Metallogels , 2021, Colloids and Surfaces A: Physicochemical and Engineering Aspects.

[19]  W. Qingqing,et al.  Synthesis and Properties Study of Bis-pyridine Derivative Gel System , 2021 .

[20]  R. Cao,et al.  Recent progress in the removal of mercury ions from water based MOFs materials , 2021 .

[21]  You‐Ming Zhang,et al.  A mechanically self-locked gemini-[1]rotaxane-assembled microsphere and its properties on l-Arg controlled reversible morphology and fluorescence changes , 2021, Journal of Materials Chemistry C.

[22]  N. Khashab,et al.  Water compatible supramolecular polymers: recent progress. , 2021, Chemical Society reviews.

[23]  Eric A. Appel,et al.  Translational Applications of Hydrogels , 2021, Chemical reviews.

[24]  T. Yi,et al.  Fluorescent supramolecular self-assembly gels and their application as sensors: A review , 2021 .

[25]  Ying‐Feng Han,et al.  Strategies for the construction of supramolecular assemblies from poly-NHC ligand precursors , 2021, Science China Chemistry.

[26]  Min Chen,et al.  Angle-independent responsive organogel retroreflective structural color film for colorimetric sensing of humidity and organic vapors , 2021 .

[27]  D. Adams,et al.  Stimuli responsive dynamic transformations in supramolecular gels. , 2021, Chemical Society reviews.

[28]  Xiao‐Qi Yu,et al.  Small molecular fluorescent probes for the detection of lead, cadmium and mercury ions , 2021 .

[29]  Qi Wei,et al.  Optically actuating ultra-stable radicals in a large π-conjugated ligand constructed photochromic complex , 2021, Science China Chemistry.

[30]  Nan Song,et al.  A stimuli-responsive pillar[5]arene-based hybrid material with enhanced tunable multicolor luminescence and ion-sensing ability , 2020, National science review.

[31]  Caizhen Zhu,et al.  AIE-Active Macromolecules: Designs, Performances, and Applications , 2021, Polymer Chemistry.

[32]  Z. Lei,et al.  A versatile synthetic approach to tunable dual-emissive Pdots with very small-size based on amphiphilic block copolymers for cell imaging , 2021 .

[33]  Xiaoxuan Zhang,et al.  Bio-inspired wettability patterns for biomedical applications. , 2021, Materials horizons.

[34]  L. Qi,et al.  Helically Grooved Gold Nanoarrows: Controlled Fabrication, Superhelix, and Transcribed Chiroptical Switching , 2020 .

[35]  You‐Ming Zhang,et al.  Pillar[5]arene-based supramolecular AIE hydrogel with white light emission for ultrasensitive detection and effective separation of multianalytes , 2020 .

[36]  Jing Li,et al.  Functional metal-organic frameworks as effective sensors of gases and volatile compounds. , 2020, Chemical Society reviews.

[37]  S. Bai,et al.  A Strategy for the Construction of Triply Interlocked Organometallic Cages by Rational Design of Poly-NHC Precursors. , 2020, Journal of the American Chemical Society.

[38]  Panpan Li,et al.  Hydrogels and Hydrogel-Derived Materials for Energy and Water Sustainability. , 2020, Chemical reviews.

[39]  Xudong Yu,et al.  Free radical oxidation reaction for selectively solvatochromic sensors with dynamic sensing ability , 2020 .

[40]  N. Khashab,et al.  Functional Supramolecular Polymeric Networks: The Marriage of Covalent Polymers and Macrocycle-Based Host-Guest Interactions. , 2020, Chemical reviews.

[41]  K. Rissanen,et al.  Steroidal supramolecular metallogels. , 2020, Chemical Society reviews.

[42]  Yan Yu,et al.  Guidelines and trends for next-generation rechargeable lithium and lithium-ion batteries. , 2020, Chemical Society reviews.

[43]  Xiaohong Cheng,et al.  α-Cyanostilbene and fluorene based bolaamphiphiles: synthesis, self-assembly, and AIEE properties with potential as white-light emissive materials and light-emitting liquid crystal displays , 2020 .

[44]  Qijuan Yuan,et al.  Progress on intelligent hydrogels based on RAFT polymerization: Design strategy, fabrication and the applications for controlled drug delivery , 2020 .

[45]  Junwei Zhao,et al.  Double-Oxalate-Bridging Tetralanthanide Containing Divacant Lindqvist Isopolytungstates with an Energy Transfer Mechanism and Luminous Color Adjustablility Through Eu3+/Tb3+ Codoping. , 2019, Inorganic chemistry.

[46]  You‐Ming Zhang,et al.  A bi-component supramolecular gel for selective fluorescence detection and removal of Hg2+ in water. , 2019, Soft matter.

[47]  X. Bu,et al.  In-situ synthesis of molecular magnetorefrigerant materials , 2019, Coordination Chemistry Reviews.

[48]  Yongsheng Yu,et al.  Multifunctional fluorescent naphthalimide self-assembly system for the detection of Cu2+ and K+ and continuous sensing of organic amines and gaseous acids , 2019, Journal of Materials Chemistry C.

[49]  Dong‐sheng Li,et al.  A Highly Stable Bi-Microporous MOF with Cubane [Ni4(OH)4] Cluster and Pore Space Partition for Electrocatalytic Methanol Oxidation Reaction. , 2019, Angewandte Chemie.

[50]  Dong‐sheng Li,et al.  Bi‐Microporous Metal–Organic Frameworks with Cubane [M 4 (OH) 4 ] (M=Ni, Co) Clusters and Pore‐Space Partition for Electrocatalytic Methanol Oxidation Reaction , 2019, Angewandte Chemie.

[51]  Qichun Zhang,et al.  Surfactants as promising media in the field of metal-organic frameworks , 2019, Coordination Chemistry Reviews.

[52]  Yicheng Yu,et al.  Multifunctional supramolecular self-assembly system for colorimetric detection of Hg2+, Fe3+, Cu2+ and continuous sensing of volatile acids and organic amine gases. , 2019, Nanoscale.

[53]  Yan Wang,et al.  Supramolecular Assembly-Induced Emission Enhancement for Efficient Mercury(II) Detection and Removal. , 2019, Journal of the American Chemical Society.

[54]  M. Liu,et al.  Helical Nanostructures: Chirality Transfer and a Photodriven Transformation from Superhelix to Nanokebab. , 2018, Angewandte Chemie.

[55]  F. Rouhani,et al.  Simple One-Pot Preparation of a Rapid Response AIE Fluorescent Metal-Organic Framework. , 2018, ACS applied materials & interfaces.

[56]  Jinhong Guo,et al.  Electrochemical microfluidics techniques for heavy metal ion detection. , 2018, The Analyst.

[57]  Aiping Gao,et al.  Terminal Molecular Isomer-Effect on Supramolecular Self-Assembly System Based on Naphthalimide Derivative and Its Sensing Application for Mercury(II) and Iron(III) Ions. , 2018, Langmuir : the ACS journal of surfaces and colloids.

[58]  You‐Ming Zhang,et al.  Pillar[5]arene-based multifunctional supramolecular hydrogel: multistimuli responsiveness, self-healing, fluorescence sensing, and conductivity , 2018 .

[59]  Ke-Qin Zhang,et al.  Rational design of materials interface at nanoscale towards intelligent oil-water separation. , 2018, Nanoscale horizons.

[60]  Zhentao Huang,et al.  A dual-mode turn-on fluorescent BODIPY-based probe for visualization of mercury ions in living cells. , 2016, The Analyst.

[61]  Qichun Zhang,et al.  A Robust Luminescent Tb(III)-MOF with Lewis Basic Pyridyl Sites for the Highly Sensitive Detection of Metal Ions and Small Molecules. , 2016, Inorganic chemistry.

[62]  Manoj Kumar,et al.  A TICT based NIR-fluorescent probe for human serum albumin: a pre-clinical diagnosis in blood serum. , 2016, Chemical communications.

[63]  A. Kazlauciunas,et al.  A vegetable oil-based organogel for use in pH-mediated drug delivery. , 2015, Soft matter.

[64]  You‐Ming Zhang,et al.  A "keto-enol tautomerization"-based response mechanism: a novel approach to stimuli-responsive supramolecular gel. , 2015, Chemical communications.

[65]  Ayyappanpillai Ajayaghosh,et al.  Functional π-gelators and their applications. , 2014, Chemical reviews.

[66]  Arben Merkoçi,et al.  Recent trends in macro-, micro-, and nanomaterial-based tools and strategies for heavy-metal detection. , 2011, Chemical reviews.

[67]  Richard G. Weiss,et al.  Molecular Gels: Materials with Self-Assembled Fibrillar Networks , 2005 .

[68]  D W Boening,et al.  Ecological effects, transport, and fate of mercury: a general review. , 2000, Chemosphere.