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Controlling molecular assembly on time scale:Time-dependent multicolor fluorescence for information encryption

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Chinese Chemical Letters 2024年第7期35卷 336-340页

作者： Zixi Zou Jingyuan Wang Yian Sun Qian Wang da-hui qu Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center School of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai 200237China

Dynamic assembly on time scale is common in biological systems but rare for artificial materials,especially for smart luminescent *** molecular assembly in a spatio-temporal manner and resulting in white-light-including multicolor fluorescence with time-dynamic features remains ***,controlling molecular assembly on time scale is achieved by integrating a pH-responsive motif to a transient alkaline solution which is fabricated by activators(NaOH)and deactivators(esters),leading to automatic assembly on time scale and time-dependent multicolor fluorescence changing from blue to white and *** kinetics of the assembly process is dependent on the ester hydrolysis process,which can be controlled by varying ester concentrations,temperature,initial pH,stirring rate and ester *** dynamic fluorescent system can be further developed for intelligent fluorescent materials such as fluorescent ink,three-dimension(3D)codes and even four-dimension(4D)codes,exhibiting a promising potential for information encryption.

关键词： Supramolecular chemistry Multicolor fluorescence White light emission Time-dependent fluorescence Information encryption

Enhancing the deep-red/near-infrared fluorescence of higher rylene diimides via the chalcogen-annulation strategy

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Science China Chemistry 2024年第4期67卷 1324-1333页

作者： Kai Chen Xiao Chen Ke Hu Yilun Zhao Yujian Liu Guogang Liu Jinquan Chen Wei Jiang Zhigang Shuai da-hui qu Zhaohui Wang Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research CenterFrontiers Science Center for Materiobiology and Dynamic ChemistryInstitute of Fine ChemicalsSchool of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai 200237China Key Laboratory of Organic Optoelectronics and Molecular Engineering Department of ChemistryTsinghua UniversityBeijing 100084China State Key Laboratory of Precision Spectroscopy East China Normal University500 Dongchuan RoadShanghai 200241China

Deep-red/near-infrared fluorescence is highly suitable for bioimaging owing to its ability to deeply penetrate tissues,organs,and live ***,developing organic fluorophores with high deep-red/near-infrared fluorescence quantum yield(Φ_(FL))and fluorescent brightness remain a significant challenge owing to the energy gap ***,we developed a straightforward and effective chalcogen-annulation strategy by introducing O,S and Se into the bay region of TDI and QDI fluorophores,realizing the increase ofΦFLand fluorescent brightness up to 10 *** our best knowledge,this study potentially stands as the pioneering instance showcasing the anti-heavy-atom effect of chalcogens,and the absoluteΦFL(93%)and fluorescent brightness(128,200 cm^(-1)mol^(-1)L)of Se-TDI is among top deep-red/near-infrared organic fluorophores currently *** femtosecond transient absorption(fs-TA)measurements show the absence of obvious changes of the excited state lifetime after the introduction of chalcogens in TDI and QDI fluorophores,indicating that intersystem crossing(ISC)can be neglected in TDI and QDI *** calculations further reveal the chalcogen-annulation strategy increase the radiative rates and reduce the reorganization energy of several accepting modes at the ground state in TDI fluorophores,leading to the suppression of internal conversion(IC)*** chalcogen-annulation strategy,which effectively increases the Φ_(FL)and restricts the IC processes,while remaining unaffected by the heavy-atom effect,offers novel insights and theoretical support for the design and synthesis of deep-red/near-infrared organic fluorophores with high Φ_(FL)and fluorescent brightness.

关键词： π-extended rylene diimides chalcogen-annulation strategy deep-red/near-infrared fluorescence

Visible Light-Induced Collapse of Molecular Microcrystals into Droplets by E-to-Z Photoisomerization and Melting Phase Transition

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CCS Chemistry 2024年第4期6卷 1071-1084页

作者： Tian-Yi Xu Min Cui Chengxi Zhao Shang-Wu Zhou Tian-Le Zhang hui-Yao Lin Fei Tong da-hui qu Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center School of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai 200237

Harnessing photoresponsive behavior in organic crystals,such as shape and morphology deformation,on multiple scales is intriguing with respect to precise spatiotemporal operation,because dynamic deformations are promising in fabricating future intelligent ***,we synthesized a new photoresponsive molecular crystal composed of dimethyl(E)-2-(3-(naphthalen-1-yl)allylidene)malonate((E)-DNAM)that undergoes E-to-Z photoisomerization accompanied by photoinduced crystal-to-liquid melting phase transition when exposed to visible *** of expanding in bulk polycrystals,single-crystal(E)-DNAM rectangular microplates in an aqueous solution rapidly collapsed into liquid droplets,showing a remarkable drastic reduction in surface area of more than 97%after light *** deduce that the unique microscopic morphology of microplates with high aspect ratios of length-tothickness reaching up to 1000 is mainly responsible for the photoinduced melting leading to drastic *** addition,the cohesive forces of liquid photoproduct facilitate the overall deformations and *** have shown a facile way to achieve the remarkable collapse of molecular crystals into droplets by photochemical reaction and phase transition.

关键词： molecular crystals crystal-to-liquid transition extreme deformations photochemistry crystal engineering flexible crystals

人工分子机器:分子尺度运动的精准化与可视化

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中国科学：化学 2024年第5期54卷 689-702页

作者：秦文煜施晨宇顾睿锐曲大辉华东理工大学结构可控先进功能材料及其制备教育部重点实验室费林加诺贝尔奖科学家联合研究中心材料生物学与动态化学前沿科学中心精细化工研究所化学与分子工程学院上海200237

分子机器在自然界至关重要,其在生物过程中执行了大量复杂的功能,从而实现不同尺度的动态行为调控.受生物系统的启发,科学家致力于研究人工分子机器在分子尺度下的精准构筑和定向运动,并通过层级组装实现信号传递和功能放大,从而推动动... 详细信息

分子机器在自然界至关重要,其在生物过程中执行了大量复杂的功能,从而实现不同尺度的动态行为调控.受生物系统的启发,科学家致力于研究人工分子机器在分子尺度下的精准构筑和定向运动,并通过层级组装实现信号传递和功能放大,从而推动动态智能材料的设计发展.但如何利用新方法精准构筑复杂的人工分子机器,如何将分子尺度的运动动态进行“可视化”,以及如何在生命科学研究中发挥其功能,一直是分子机器领域的研究热点.本文基于本课题组的工作,系统介绍了人工分子机器在分子尺度的精准结构构筑、信号输出以及其在跨膜运输方面的研究.最后总结了该领域在多尺度精细化和功能化方面的挑战,并展望了分子机器在宏观智能材料领域的发展前景.

关键词：分子机器机械互锁分子分子马达光学信号表征跨膜运输

基于雷洛昔芬的多重刺激响应性单组分室温磷光分子晶体

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Science Bulletin 2024年第9期69卷 1237-1248页

作者：潘智超宋金明张莎莎曾平梅菊曲大辉 Key Laboratory for Advanced Materials Joint International Research Laboratory of Precision Chemistry and Molecular EngineeringFeringa Nobel Prize Scientist Joint Research CenterFrontiers Science Center for Materiobiology and Dynamic ChemistryInstitute of Fine ChemicalsSchool of Chemistry&Molecular EngineeringEast China University of Science&TechnologyShanghai 200237China

Simultaneously achieving room-temperature phosphorescence(RTP) and multiple-stimuli responsiveness in a single-component system is of significance but remains challenging. Crystallization has been recognized to be a workable strategy to fulfill the above task. However, how the molecular packing mode affects the intersystem crossing and RTP lifetime concurrently remains unclear so far. Herein, four economic small-molecular compounds, analogues of the famous drug raloxifene(RALO), are facilely synthesized and further explored as neat single-component and stimuli-responsive RTP emitters via crystallization engineering. Thanks to their simple structures and high ease to crystallize, these raloxifene analogues function as models to clarify the important role of molecular packing in the RTP and stimuliresponsiveness properties. Thorough combination of the single-crystal structure analysis and theoretical calculations clearly manifests that the tight antiparallel molecular packing mode is the key point to their RTP behaviors. Interestingly, harnessing the controllable and reversible phase transitions of the two polymorphs of RALO-OAc driven by mechanical force, solvent vapor, and heat, a single-component multilevel stimuli-responsive platform with tunable emission color is established and further exploited for optical information encryption. This work would shed light on the rational design of multi-stimuli responsive RTP systems based on single-component organics.

关键词： Crystal engineering Molecular packing Organic room-temperature phosphorescence(RTP) Polymorph Stimuli-responsiveness

Recent advances in new-type molecular switches

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Science China Chemistry 2015年第6期58卷 916-921页

作者： Hong Li da-hui qu Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science & Technology

Molecular switches that can undergo reversible switching between two or more different states in response to external stimuli have been used in the fabrication of various optoelectronic devices and smart materials for many decades, and also found many applications in sensing, molecular self-assembly and photo-controlled biological systems. Recently, mechanically interlocked molecules, such as rotaxanes and catenanes, and molecular rotary motors based on overcrowded alkenes have emerged as two new kinds of molecular switches. Some novel applications of above-mentioned molecular switches have been discovered. In this mini review, we mainly highlight noticeable achievements over the past decade in this field, and summarize the applications of new types of molecular switches, for instance, controlling the chiral space to regulate catalytic reaction as organocatalysts, controlling molecular motions, synthesizing a peptide in a sequence-specific manner and modulating the wettability of the self-assembled monolayers.

关键词： molecular switches rotaxane molecular motor stimuli-responsive function

Cucurbit[8]uril-mediated multi-color fluorescence system for time-dependent information encryption

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Science China Chemistry 2023年第4期66卷 1111-1119页

作者： Biyan Lin Qian Wang Zhen Qi Hanren Xu da-hui qu Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research CenterInstitute of Fine ChemicalsFrontiers Science Center for Materiobiology and Dynamic ChemistrySchool of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai 200237China

Programming microscopic assembly mode to control macroscopic property is an attractive research *** particular,controlling molecular assembly to control fluorescence is of considerable interest for developing smart fluorescent ***,a color-tunable supramolecular emissive system was developed based on cucurbit[8]uril mediated host-guest *** designing for the molecular structures with minimized change resulted in different assembly modes and hence generating distinctive fluorescence,including green,yellow and orange with the addition of cucurbit[n]*** advantage of this feature,the advanced information encryption material(4D code)with multiple encryption levels and time-dependent encryption feature was *** a code was dynamic on time scale,generating a series of 3D codes with *** encrypted information only can be recognized by integrating time-coursed *** work provides a new insight for designing intelligent fluorescent materials for information encryption with high level of security.

关键词： host-guest systems fluorescence multi-color emission information encryption cucurbituril

Visualizing Aβdeposits in live young AD model mice with a simple red/near-infrared-fluorescent AIEgen

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Science China Chemistry 2022年第2期65卷 339-352页

作者： Yipu Wang Dong Mei Xinyi Zhang da-hui qu Ju Mei Key Laboratory for Advanced Materials Feringa Nobel Prize Scientist Joint Research CenterFrontiers Science Center for Materiobiology and Dynamic ChemistryJoint International Research Laboratory for Precision Chemistry and Molecular EngineeringInstitute of Fine ChemicalsSchool of Chemistry&Molecular EngineeringEast China University of Science&TechnologyShanghai 200237China Clinical Research Center Beijing Children’s HospitalCapital Medical UniversityNational Center for Children’s HealthBeijing 100045China

Precise and early detection ofβ-amyloid(Aβ)deposits in situ and in real time is pivotal to the diagnosis and early intervention of Alzheimer’s disease(AD).Optical imaging stands out to be a promising technique for such a task;however,it still remains a big challenge,due to the lack of high-performance imaging contrast *** by poor blood-brain barrier(BBB)penetrability,short-wavelength excitation and emission,as well as the aggregation-caused quenching effect,the widely used goldstandard probes cannot be used for early in-vivo imaging of Aβ***,we integrate the Aβdeposits-favored geometry,amphiphilic and zwitterionic molecular structure,extended D-π-A electronic structure,and 3 D conformation into one molecule,facilely establishing a simple and economic imaging contrast agent that enjoys high specificity and affinity to Aβdeposits,good BBB penetrability,bright red/near-infrared fluorescence,low interference from autofluorescence,aggregation-induced emission(AIE)feature,high signal-to-noise ratio(SNR),and high ***-vitro,ex-vivo,and in-vivo experiments with different strains of mice indicate that AIE-CNPy-AD holds the universality to Aβdeposits ***,AIE-CNPy-AD is even able to precisely trace the small and sparsely-distributed Aβdeposits in AD model mice as young as 4-month-old APP/PS1 mice,the youngest having Aβ***,the present probe could clearly reveal the increase and enlargement of Aβdeposits as the mice ***,AIE-CNPy-AD might be an ideal alternative for early AD diagnosis and highly reliable monitoring of AD progression.

关键词： Aβdeposits AIE Alzheimer’s disease(AD) red/NIR fluorescence in-vivo imaging diagnosis

Constructing supramolecular polymers from phototrigger containing monomer

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Chinese Chemical Letters 2018年第11期29卷 1621-1624页

作者： Xiuli Zheng Qi Miao Wenzhi Wang da-hui qu Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecular EngineeringEast China University of Science &Technology

A new type of photo-induced supramolecular polymer was fabricated by host-guest interaction from a phototrigger containing building block. A dibenzo-24-crown-8 （DB24C8） macrocycle and dibenzylammonium （DBA） site containing linear monomer was designed and synthesized. The coumarin, as a photocleavable protector, was introduced to the terminal of the monomer. When exposed to the UV light, the coumarin unit would be cleavaged and the monomer without terminal coumarin can self-assemble into supramolecular polymers via the host-guest interaction between DB24C8 moieties and DBA units. Increasing the concentration of the monomer, the supramolecular polymers will convert to supramolecular organogel by cross-linking with each other.

关键词： Supramolecular polymer Host-guest recognition Photo-responsive Crown ether