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1.
Jiayi Xu Yahui Zhang Menghan Wang Prof. Yu Gao Prof. Haijun Chen 《European journal of organic chemistry》2023,26(40):e202300833
Organic fluorophores with highly efficient luminescence in both solution and solid states have attracted significant attention due to their ability to circumvent the limitations of aggregation-caused quenching and aggregation-induced emission type molecules. However, their development and wide-range applications are hampered by extremely complex synthetic methodologies and limited frameworks with dual-state emission (DSE) structural characteristics. In sharp contrast to the reported luminogens with big and planar π systems or highly conjugated and twisted structures, we discovered novel three-dimensional scaffolds in one molecule to achieve DSE. These molecules allowing for rapid access showed completely different molecular packing manners from those of planar conjugated molecules and exhibited excellent optoelectronic properties with diminished intermolecular π−π stacking interactions due to steric hindrance. Our findings should open new avenues for designing DSE molecules with new frameworks, which will enable more successful development of dual-state emitters for their broad applications in the future. 相似文献
2.
Wang Zhang Yuan Yongming Zhang 《Journal of polymer science. Part A, Polymer chemistry》2017,55(4):560-574
Nonconventional luminogens without classic conjugated structures have drawn increasing interests owing to their fundamental importance and promising applications. These luminogens generally bear such subgroups as tertiary amine, C = C, C≡N, C = O, OH, ether, and imide. The emission mechanism, however, remains under debate. Different assumptions like oxidation or acidification of tertiary amines, aggregation of C = O groups, as well as clustering and electron cloud overlap are proposed. Unlike concentration quenching and aggregation-caused quenching (ACQ) that are normally observed in traditional luminogens, many of these unorthodox luminogens exhibit unique aggregation-induced emission (AIE) characteristics, regardless of their molecular architectures. This review summarizes varying unorthodox luminogens with AIE features, aiming to outline the recent advances in this exciting area, with focus on the macromolecular systems. In light of the reported results, clustering-triggered emission mechanism, namely clustering of diverse subgroups with subsequent electron cloud overlap and conformation rigidification can well rationalize the photophysical behaviors of most systems. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 560–574 相似文献
3.
Dr. Biao Chen Wenhuan Huang Hao Su Prof. Hui Miao Dr. Xuepeng Zhang Prof. Guoqing Zhang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(25):10109-10112
Organic luminogens with persistent room-temperature phosphorescence (RTP) have found a wide range of applications. However, many RTP luminogens are prone to severe quenching in the crystalline state. Herein, we report a strategy to construct a donor-sp3-acceptor type luminogen that exhibits aggregation-induced emission (AIE) while the donor-sp2-acceptor counterpart structure exhibits a non-emissive solid state. Unexpectedly, it was discovered that a trace amount (0.01 %) of the structurally similar derivative, produced by a side reaction with the DMF solvent, could induce strong RTP with an absolute RTP yield up to 25.4 % and a lifetime of 48 ms, although the substance does not show RTP by itself. Single-crystal XRD-based calculations suggest that n–σ* orbital interactions as a result of structural similarity may be responsible for the strong RTP in the bicomponent system. This study provides a new insight into the design of multi-component, solid-state RTP materials from organic molecular systems. 相似文献
4.
Aggregation‐induced emission luminogens (AIEgens) are a new class of luminophors, which are non‐emissive in solution, but emit intensively upon aggregation. By properly designing the chemical structures of the AIEgens, their aggregation process can be tuned towards a desired direction to give diverse novel luminescent architectures of micelles, rods, and helical fibers. AIEgens represent a kind of promising building block for the fabrication of luminescent micro/nanostructures with controllable morphologies. In this review, we describe our recent work in this research area, focusing on the molecular design, circularly polarized luminescence properties, and helical self‐assembly behavior of AIEgens. 相似文献
5.
Zuping Xiong Xiaoxiao Zhang Longxiang Liu Qiaozhi Zhu Zhenni Wang Hui Feng Zhaosheng Qian 《Chemical science》2021,12(32):10710
It is extremely challenging but desirable to regulate the photophysical and photochemical processes of aggregation-induced emission luminogens (AIEgens) in distinct states in a controllable manner. Herein, we design two groups of AIEgens based on a triphenylacrylonitrile (TPAN) skeleton with through-space conjugation (TSC) property, demonstrate controlled regulation of photophysical emission efficiency/color and photochemical photochromic and photoactivatable fluorescence behaviours of these compounds, and further validate design principles to achieve highly efficient and emission-tuning AIEgens and to accomplish photo-dependent color switches and fluorescence changes. It is surprisingly found that the introduction of heavy halogens like bromine into a TPAN skeleton dramatically enhances the emission efficiency, and such an abnormal phenomenon against the heavy-atom effect is attributed to the specific through-space conjugation nature of the AIE-active skeleton, effective intermolecular halogen-bond-induced restriction of intramolecular motions, and heavy atom-induced vibration reduction. The incorporation of two electron-donating amino groups into the TPAN skeleton cause the luminogens to undergo a bathochromic shifted emission due to the formation of a D–A pattern. Apart from the regulation of photophysical processes in the solid state, the construction of the D–A pattern in luminogens also results in extremely different photochemical reactions accompanying reversible/irreversible photochromism and photoactivatable fluorescence phenomena in a dispersed state. It is revealed that photo-triggered cyclization and decyclization reactions dominantly contribute to reversible photochromism of the TPAN family, and the photo-induced cyclization–dehydrogenation reaction is responsible for the irreversible color changes and photoactivatable fluorescence behaviours of the NTPAN family. The demonstrations of multiple-mode signaling in photoswitchable patterning and information encryption highlight the importance of controlled regulation of photophysics and photochemistry of fused chromic and AIE-active luminogens in distinct states.Highly efficient aggregation-induced emission, reversible and irreversible photochromism are achieved by regulating heavy halogen-regulated photophysics and D–A molecular pattern-controlled photochemistry of through-space conjugated luminogens. 相似文献
6.
Lihao Guo Xiao Yu Jiahui Du Prof. Dr. Wei Li Prof. Dr. Vladimir Bregadze Dr. Deshuang Tu Prof. Dr. Changsheng Lu Prof. Dr. Hong Yan 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(33):e202200303
We proposed a new molecular design strategy that the o-carboranyl group is attached as “an innocent unit” to the remote side of luminogens to tune photophysical properties. To verify this strategy, two o-carborane-based compounds with asymmetric molecular geometry were designed and synthesized. Photophysical properties of o-carborane-based luminogens were investigated on the basis of UV-Vis spectra, photoluminescence spectra, crystal structure analysis and theoretical calculations. The results indicate that the o-carboranyl group has a slight effect on the energy gap between the ground state (S0) and the first excited state (S1) in the solution state but a significant effect on the energy gap between S0 and S1 in the solid state. Besides, the radiative and non-radiative transition processes are modulated by the o-carboranyl unit. This leads to emission quenching in the solution state but an enhanced luminous efficiency in the aggregate state with a typical aggregation-induced emission (AIE) property. 相似文献
7.
Nonconventional luminophores without large conjugated structures are attracting increasing attention for their unique aggregation-induced emission(AIE)properties and promising applications in optoelectronic and biomedical areas.The emission mechanism,however,remains elusive,which makes rational molecular design difficult.Recently,we proposed the clustering-triggered emission(CTE)mechanism to illustrate the emission.The clustering of electron-rich nonconventional chromophores withπand/or n electrons and consequent electron cloud overlap is crucial to the luminescence.Herein,based on the CTE mechanism,nonaromatic polymers containing multitype heteroatoms(i.e.,O,N,and S)and involving amide(CONH)and sulfide(-S-)groups were designed and synthesized through facile thiol-ene click chemistry.The resulting polymers demonstrated typical concentration-enhanced emission,AIE phenomenon,and excitation-dependent emission.Notably,compared with polysulfides,these polymers exhibited much higher solid-state emission efficiencies,because of the incorporation of amide units,which contributed to the formation of emissive clusters with highly rigidified conformations through effective hydrogen bonding.Furthermore,distinct persistent cryogenic phosphorescence or even room temperature phosphorescence(RTP)was noticed.These photophysical behaviors can well be rationalized in terms of the CTE mechanism,indicating the feasibility of rational molecular design and luminescence regulation. 相似文献
8.
Hao Zhang Dr. Frank Rominger Prof. Dr. Uwe H. F. Bunz Dr. Jan Freudenberg 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(48):11218-11222
The synthesis, properties and X-ray single-crystal structures of two regioisomeric triphenyl tristyrylbenzenes are reported. Both C3v and Cs derivatives display aggregation-induced emission (AIE) behavior. Regioisomerism impacts the solid-state intermolecular interactions, the photophysical characteristics and photostability in solution. 相似文献
9.
Dr. Ying-Chen Duan Dr. Qing-Qing Pan Zhi-Wen Zhao Dr. Ying Gao Dr. Yong Wu Dr. Liang Zhao Dr. Yun Geng Dr. Min Zhang Prof. Zhong-Min Su 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(37):9571-9579
Quantum mechanical and molecular dynamics simulations have been carried out on a series of anthracene-o-carborane derivatives (ANT-H, ANT-Ph, ANT-Me and ANT-TMS) with rare red-light emission in the solid state. The simulation of the heating process of the crystals and further comparison of the molecular structures and excited-state properties before and after heating help us to disclose the thermochromic behavior, that is, the red-shift emission is caused by elongation of the C1−C2 bond in the carborane moiety after heating. Thus, we believe that the molecular structure in the crystal is severely affected by heating. Transformation of the molecular conformation appears in the ANT-H crystal with increasing temperature. More specifically, the anthracene moiety moves from nearly parallel to the C1−C2 bond to nearly perpendicular, causing the short-wavelength emission to disappear after heating. As for the aggregation-induced emission phenomenon, the structures and photophysical properties were investigated comparatively in both the isolated and crystal states; the results suggested that the energy dissipation in crystal surroundings was greatly reduced through hindering structure relaxation from the excited to the ground state. We expect that discussion of the thermochromic behavior will provide a new analysis perspective for the molecular design of o-carborane derivatives. 相似文献
10.
Dr. Francesco Foschi Kevin Synnatschke Sebastian Grieger Dr. Wen-Shan Zhang Prof. Dr. Hubert Wadepohl Prof. Dr. Rasmus R. Schröder Dr. Claudia Backes Prof. Dr. Lutz H. Gade 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(19):4269-4280
New luminogens for aggregation-induced emission (AIE), which are characterized by a branched cross-conjugated 2,6-bis(1,2,2-triarylvinyl)pyridine motif, have been synthesized exploiting the one-pot Ti-mediated tetraarylation of 2,6-bis(arylethynyl)pyridines. Thin layer solid-state emitters were prepared by spin-coating of the luminogens, while AIE-colloidal dispersions were investigated in terms of optical density and scattering behaviour. This has given insight into particle size distributions, time evolution of the aggregation and the influence of different functionalization patterns on the luminescence of molecular aggregates. In particular, a combination of extinction spectroscopy and dynamic light scattering is being proposed as a powerful method for investigating the dynamic aggregation process in AIE-type colloids. 相似文献
11.
Abdusalom A. Suleymanov Dr. Albert Ruggi Ophélie Marie Planes Dr. Anne-Sophie Chauvin Dr. Rosario Scopelliti Dr. Farzaneh Fadaei Tirani Dr. Andrzej Sienkiewicz Alberto Fabrizio Prof. Dr. Clémence Corminboeuf Prof. Dr. Kay Severin 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(27):6718-6721
Highly substituted Δ3-1,2,3-triazolines can be prepared by reaction of triarylvinyl Grignard reagents with functionalized organic azides. The heterocycles are fluorescent in the solid state, and—depending on the substituents—they can display aggregation-induced emission. Upon oxidation, the triazolines form stable radical cations with altered photophysical properties. Therefore, they represent rare examples of solid-state emitters with intrinsic electrofluorochromic behavior. 相似文献
12.
Jiajie Zeng Jingjing Guo Hao Liu Jacky W. Y. Lam Zujin Zhao Shuming Chen Ben Zhong Tang 《化学:亚洲杂志》2019,14(6):828-835
Aggregation‐induced delayed fluorescence (AIDF) can be regarded as a special case of aggregation‐induced emission (AIE). Luminogens with AIDF can simultaneously emit strongly in solid state and fully utilize the singlet and triplet excitons in organic light‐emitting diodes (OLEDs). In this work, two new AIDF luminogens, DMF‐BP‐DMAC and DPF‐BP‐DMAC, with an asymmetric D–A–D′ structure, are designed and synthesized. The characteristics of both luminogens are systematically investigated, including single crystal structures, theoretical calculations, photophysical properties and thermal stabilities. Inspired by their AIDF nature, the green‐emission non‐doped OLEDs based on them are fabricated, which afford good electroluminescence performances, with low turn‐on voltages of 2.8 V, high luminance of 52560 cd m?2, high efficiencies of up to 14.4 %, 42.3 cd A?1 and 30.2 lm W?1, and very small efficiency roll‐off. The results strongly indicate the bright future of non‐doped OLEDs on the basis of robust AIDF luminogens. 相似文献
13.
Hongqin Jiang Linhuang Xie Zhiming Duan Kunhua Lin Prof. Qing He Vincent M. Lynch Prof. Jonathan L. Sessler Prof. Hongyu Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(60):15006-15012
We report here a set of fluorescent supramolecular organic frameworks (SOFs) that incorporate aggregation-induced emission (AIE) units within their frameworks. The fluorescent SOFs of this study were constructed by linking the tetraphenylethylene (TPE)-based tetra(amidinium) cation TPE4+ and aromatic dicarboxylate anions through amidinium-carboxylate salt bridges. The resulting self-assembled structures are characterized by fluorescence quantum yields in the range of 4.6∼14 %. This emissive behavior is ascribed to a combination of electrostatic interactions and hydrogen bonds that operate in concert to impede motions that would otherwise lead to excited state energy dissipation. Single-crystal X-ray diffraction analyses revealed that the length of the dicarboxylate anion bridges has a considerable impact on the structural features of the resulting frameworks. Nevertheless, all SOFs prepared in the context of the present study were found to display emissive features characteristic of TPE-based AIE luminogens with only a modest dependence on the structural specifics being seen. The SOFs reported here could be reversibly “broken up” and “reformed” in response to acid/base stimuli. This reversible structural behavior is consistent with their SOF nature. 相似文献
14.
Wanting Yu Dr. Xiaoxiao Yu Dr. Zhenduo Qiu Dr. Chengjian Xu Dr. Mengyue Gao Dr. Junjie Zheng Dr. Junyan Zhang Prof. Gang Wang Prof. Yanhua Cheng Prof. Meifang Zhu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(55):e202201664
Mesoscopic aggregate is important to transfer or even amplify the molecular information in macroscopic materials. As an important branch of aggregate science, aggregation-induced emissive luminogens (AIEgens) often show slight or even no emission in solutions but exhibit bright emission when they aggregate, which open a new avenue for the practical applications. Due to the flexible and rotor structure of AIEgens, the aggregate structure of AIEgens is highly sensitive to the surrounding microenvironment, resulting in adjustable optical properties. Fibers integrated of a multiplicity of functional components are ideal carriers to control the aggregation processes, further assembly of fibers produces large-scale fabrics with amplified functions and practical values. In this Concept article, we focus on the latest advances on the synergy between “AIE+Fiber” for the boosted performance that beyond AIE, and their applications are presented and abstracted out to stimulate new ideas for developing “AIE+Fiber” systems. 相似文献
15.
Dr. Satoshi Suzuki Dr. Shunsuke Sasaki Amir Sharidan Sairi Riki Iwai Prof. Dr. Ben Zhong Tang Prof. Dr. Gen-ichi Konishi 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(25):9940-9951
Twenty years ago, the concept of aggregation-induced emission (AIE) was proposed, and this unique luminescent property has attracted scientific interest ever since. However, AIE denominates only the phenomenon, while the details of its underlying guiding principles remain to be elucidated. This minireview discusses the basic principles of AIE based on our previous mechanistic study of the photophysical behavior of 9,10-bis(N,N-dialkylamino)anthracene ( BDAA ) and the corresponding mechanistic analysis by quantum chemical calculations. BDAA comprises an anthracene core and small electron donors, which allows the quantum chemical aspects of AIE to be discussed. The key factor for AIE is the control over the non-radiative decay (deactivation) pathway, which can be visualized by considering the conical intersection (CI) on a potential energy surface. Controlling the conical intersection (CI) on the potential energy surface enables the separate formation of fluorescent (CI:high) and non-fluorescent (CI:low) molecules [control of conical intersection accessibility ( CCIA )]. The novelty and originality of AIE in the field of photochemistry lies in the creation of functionality by design and in the active control over deactivation pathways. Moreover, we provide a new design strategy for AIE luminogens (AIEgens) and discuss selected examples. 相似文献
16.
Weijian Luo Yiren Zhang Yongyang Gong Qing Zhou Yongming Zhang Wangzhang Yuan 《中国化学快报》2018,29(10):1533-1536
Twisted pure organic luminogens based on benzophenone and aromatic amines exhibit both fluorescence and phosphorescence in crystals, while owning merely red-shifted fluorescence at ground amorphous solids. Some of them even demonstrate greatly enhanced emission upon grinding. 相似文献
17.
Wenhan Xu Michelle M. S. Lee Dr. Jing-Jun Nie Zhihan Zhang Dr. Ryan T. K. Kwok Dr. Jacky W. Y. Lam Dr. Fu-Jian Xu Dr. Dong Wang Prof. Ben Zhong Tang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(24):9697-9703
Photodynamic therapy (PDT) has long been shown to be a powerful therapeutic modality for cancer. However, PDT is undiversified and has become stereotyped in recent years. Exploration of distinctive PDT methods is thus highly in demand but remains a severe challenge. Herein, an unprecedented 1+1+1>3 synergistic strategy is proposed and validated for the first time. Three homologous luminogens with aggregation-induced emission (AIE) characteristics were rationally designed based on a simple backbone. Through slight structural tuning, these far-red/near-infrared AIE luminogens are capable of specifically anchoring to mitochondria, cell membrane, and lysosome, and effectively generating reactive oxygen species (ROS). Notably, biological studies demonstrated combined usage of three AIE photosensitizers gives multiple ROS sources simultaneously derived from several organelles, which gives superior therapeutic effect than that from a single organelle at the same photosensitizers concentration. This strategy is conceptually and operationally simple, providing an innovative approach and renewed awareness of improving therapeutic effect through three-pronged PDT. 相似文献
18.
Andriani Furoida Misato Daitani Kyohei Hisano Osamu Tsutsumi 《Molecules (Basel, Switzerland)》2021,26(23)
Gold(I) complexes, enabling to form linear coordination geometry, are promising materials for manifesting both aggregation-induced emission (AIE) behavior due to strong intermolecular Au–Au (aurophilic) interactions and liquid crystalline (LC) nature depending on molecular geometry. In this study, we synthesized several gold(I) complexes with rod-like molecular skeletons where we employed a mesogenic biphenylethynyl ligand and an isocyanide ligand with flexible alkoxyl or alkyl chains. The AIE behavior and LC nature were investigated experimentally and computationally. All synthesized gold(I) complexes exhibited AIE properties and, in crystal, room-temperature phosphorescence (RTP) with a relatively high quantum yields of greater than 23% even in air. We have demonstrated that such strong RTP are drastically changed depending on the crystal-size and/or crystal growth process that changes quality of crystals as well as the aggregate structure, of e.g., Au–Au distance. Moreover, the complex with longer flexible chains showed LC nature where RTP can be observed. We expect these rod-like gold(I) complexes to have great potential in AIE-active LC phosphorescent applications such as linearly/circularly polarizing phosphorescence materials. 相似文献
19.
Two new pyrene-based fluorophores, namely 1-[4-(2,2-diphenylvinyl)phenyl]pyrene (PVPP) and 1,3,6,8-tetrakis[4-(2,2-diphenylvinyl)phenyl]pyrene (TPVPP), were synthesized through Suzuki coupling reaction and well characterized. PVPP successfully suppresses the fluorescence quenching of pyrene units in the solid state, displaying aggregation-induced enhanced emission. Despite the same substituent, TPVPP shows a different fluorescent behavior. On the basis of the crystal structures, the distinct optical behavior is discussed and clarified. The intermolecular C-H?π interaction has a dramatic effect on their photophysical properties in the solid state. 相似文献
20.
Suchetha Shetty Dr. Noorullah Baig Dr. Muhieddine Safa Dr. Ridha Gharbi Dr. Santhanagopalan Sriram Dr. Firas Rasoul Prof. Dr. Bassam Alameddine 《ChemistryOpen》2021,10(10):1067-1073
We report the synthesis, characterization, and photophysical properties of novel metal oxide nanoparticles (NPs) coated with specially designed fluorescein substituents which are capped with electron-withdrawing groups. The fluorescein-coated nanoparticles were synthesized in excellent yields, and their structures were confirmed using various advanced spectroscopic, instrumental, and surface analysis techniques, revealing the formation of the target functionalized nanoparticles (FNPs) which show superior chemical and thermal stabilities. In addition, the photophysical properties of the FNPs were examined using UV-visible absorption and fluorescence spectroscopy. These latter techniques disclosed aggregation-induced emission (AIE) properties for most of the target FNPs, namely those which are soluble in common organic solvents at selective concentration ranges of water fractions in the solvent mixture. 相似文献