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One-Pot Synthesis of Spiro[fluorene-9,9'-xanthene]Derivatives

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Chinese Journal of Chemistry 2021年第3期39卷 701-709页

作者： Hao-Xuan Yuan Ying Wei ling-hai xie Wei Huang Centre for Molecular Systems and Organic Devices(CMSOD)&Key Laboratory for Organic Electronics and Information Displays&Institute of Advanced Materials(IAM)&Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM) Nanjing University of Posts&Telecommunications9 Wenyuan RoadNanjingJiangsu 210023China Shaanxi Institute of Flexible Electronics(SIFE) Northwestern Polytechnical University127 West Youyi RoadXi'anShaanxi 710072China

As a novel class of spirofluorenes,spirobifluorene(SBF)and spiro[fluo-rene-9,9'-xanthene]derivatives(SFXs)have orthogonal geometric config-uration,spiro-conjugation effect,and rigid steric hindrance,which can be widely used in the fields of synthetic chemistry,materials chemistry and supramolecular *** to their facile one-pot synthetic route,and to the variety of molecular designs,SFXs are expected to become new spiro functional materials that replace *** this review,we present the history,development and expansion of SFXs synthesis in one-pot methods,and the advantages and limitations of one-pot synthesis are also dis-cussed.

关键词： Spirofluorenes Spiro[fluorene 9,9'-xanthene]s(SFXs) One pot synthesis Synthetic methods Heterocycles Cyclization

Halogen bonding in the co-crystallization of potentially ditopic diiodotetrafluorobenzene:a powerful tool for constructing multicomponent supramolecular assemblies

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National Science Review 2020年第12期7卷 1906-1932页

作者： Xue-Hua Ding Yong-Zheng Chang Chang-Jin Ou Jin-Yi Lin ling-hai xie Wei Huang Key Laboratory of Flexible Electronics(KLOFE) & Institute of Advanced Materials(IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing Tech University(Nanjing Tech) Key Laboratory for Organic Electronics &Information Displays(KLOEID) and Institute of Advanced Materials (IAM) Jiangsu National Synergistic Innovation Center for Advanced Materials (SICAM)Nanjing University of Posts & Telecommunications(NUPT) Shaanxi Institute of Flexible Electronics(SIFE) Northwestern Polytechnical University (NPU)

Halogen bonding is emerging as a significant driving force for supramolecular self-assembly and has aroused great interest during the last two *** the various halogen-bonding donors,we take notice of the ability of 1,4-diiodotetrafluorobenzene(1,4-DITFB) to co-crystallize with diverse halogen-bonding acceptors in the range from neutral Lewis bases(nitrogen-containing compounds,N-oxides,chalcogenides,aromatic hydrocarbons and organometallic complexes) to anions(halide ions,thio/selenocyanate ions and tetrahedral oxyanions),leading to a great variety of supramolecular architectures such as discrete assemblies,1 D infinite chains and 2 D/3 D *** of them act as promising functional materials(***,phosphorescence,optical waveguide,laser,non-linear optics,dielectric and magnetism)and soft materials(*** crystal and supramolecular gel).Here we focus on the supramolecular structures of multicomponent complexes and their related physicochemical properties,highlight representative examples and show clearly the main directions that remain to be developed and improved in this *** the point of view of crystal engineering and supramolecular chemistry,the complexes summarized here should give helpful information for further design and investigation of the elusive category of halogen-bonding supramolecular functional materials.

关键词： halogen bond co-crystal physicochemical properties supramolecular chemistry crystal engineering

A Comparison Study of Physicochemical Properties and Stabilities of H-Shaped Molecule and the Corresponding Polymer

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Chinese Journal of Polymer Science 2019年第1期37卷 11-17,1-10页

作者： Quan-You Feng Bin Li Zong-Yan Zuo Song-Lin xie Meng-Na Yu Bin Liu Ying Wei ling-hai xie Rui-Dong Xia Wei Huang Center for Molecular Systems and Organic Devices (CMSOD) Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for Biosensors Institute of Advanced Materials (IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM) Nanjing University of Posts & Telecommunications Shaanxi Institute of Flexible Electronics (SIFE) Northwestern Polytechnical University (NPU)

Rare attention has been paid to the comparison between a monomer and its corresponding polymer in terms of the optoelectronic characteristics. In this article, a model H-shaped molecule and its corresponding polymer, both of which exhibited similar properties including blue emission and solution processing, were designed and synthesized. Optoelectronic properties and various kinds of stability features, including the thermostabilities, spectral stabilities and amplified spontaneous emission characteristic of the monomer and polymer were investigated. In general, the corresponding polymer PH exhibited similar optoelectronic properties but deteriorated stabilities compared with its H-shaped monomer H-1 probably owing to the similar chemical structure but the wider molecular weight distribution and metal catalyst residue. Importantly, monomer H-1 displayed a comparable ASE threshold value with its polymer PH,suggesting that H-shaped fluorene-based small molecules may be more promising optical gain media in solid state amplifers and lasers.

关键词： Fluorene H-shape Stability Optoelectronic materials

One-Pot Synthesis of Axially and Centrally Chiral A-type Nanogrids

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Chinese Journal of Chemistry 2023年第22期41卷 2969-2974页

作者： Ying Wei Xue Du Wan-Xin Huang Ming-Yang Fu Zheng Zhang Chun-Xiao Zhong Yi-Ru Wang haiFeng ling ling-hai xie Wei Huang Centrefor Molecular Systems and Organic Devices(CMSOD@IAM) State Key Laboratory of Organic Electronics and Information Displays&Institute of Advanced Materials(IAM)Nanjing University of Posts&Telecommunications9 Wenyuan RoadNanjingJiangsu 210023China Frontiers Science Centerfor Flexible Electronics(FSCFE) MIT Key Laboratory of Flexible Electronics(KLoFE)Northwestern Poly-technical UniversityXi'anShaanxi710072China

A novel type of A-type nanogrids(AGs)with axial and central chirality was synthesized via Friedel-Crafts gridization of thiophenes and difluorenyl biaromatic derivatives,yielding 9%-30%.Additionally,the effect of stereoisomers of 1,1'-binaphthyl difluorenols(BINDFOH)was investigated to demonstrate that R/S-BINDFOH is more advantageous for the synthesis of AGs than ***,tests on OFET memory devices showed that AGs have a larger storage window,indicating potential for data storage applications.

关键词： Friedel-Crafts gridization A-type nanogrids OFET Chirality Nanostructures Organic chemistry

Nondilute 1,2-Dichloroethane Solution of Poly(9,9-dioctylfluorene-2,7-diyl)：A Study on the Aggregation Process

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Chinese Journal of Polymer Science 2016年第11期34卷 1311-1318页

作者： Meng-na Yu Bin Liu 林进义 Tao Li 陆丹 Feng Liu Wen-sai Zhu ling-hai xie 黄维 Key Laboratory for Organic Electronics and Information Displays & Institute of Advanced Materials(IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing University of Posts & Telecommunications Key Laboratory of Flexible Electronics(KLOFE) & Institute of Advanced Materials(IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing Tech University(Nanjing Tech) The Blackett Laboratory Imperial College London State Key Laboratory of Supramolecular Structure and Materials College of ChemistryJilin University

Molecular aggregates in conjugated polymer（CP） solution can propagate into mesoscale morphology of the relevant film and further dominate the optoelectronic property. Herein, we probed the aggregation behavior of poly（9,9-dioctylfluorene-2,7-diyl）（PFO） and studied its influence on the photophysical property in 1,2-dichloroethane（DCE） solution, where the contents of β-phase or-aggregates increased with prolonged aging time. Thereinto, high quality β-film was fabricated from DCE solution with critical aggregate time of 6 min. The film exhibited excellent surface morphology and characteristic emission of β-phase. Meanwhile, films prepared from aged DCE solutions exhibited high crystallinity, which was promising to obtain higher photoluminance efficiency and charge transport ability simultaneously. Therefore, it is significant to get deep insight into the aggregation behavior of CP, which is involved not only with the solution-processing technology of plastic device, but also with the optoelectronic property of CP.

关键词： aggregation crystallinity conjugated aggregate optoelectronic chains propagate mesoscale insight stacking

Electrospun Supramolecular Hybrid Microfibers from Conjugated Polymers:Color Transformation and Conductivity Evolution

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Chinese Journal of Polymer Science 2021年第7期39卷 824-830页

作者： Wei Xue Man Xu Meng-Na Yu Hua-Min Sun Jin-Yi Lin Rong-Cui Jiang ling-hai xie Nai-En Shi Wei Huanga Center for Molecular Systems and Organic Devices(CMSOD) Key Laboratory for Organic Electronics and Information Displays&Institute of Advanced Materials(IAM)Nanjing University of Posts&TelecommunicationsNanjing 210023China Center for Supramolecular Optoelectronics(CSO) Key Laboratory of Flexible Electronics(KLOFE)and Institute of Advanced Materials(IAM)Nanjing Tech University(NanjingTech)Nanjing 211816China Frontiers Science Center for Flexible Electronics(FSCFE) Shaanxi Institute of Flexible Electronics(SIFE)&Shaanxi Institute of Biomedical Materials and Engineering(SIBME)Northwestern Polytechnical University(NPU)Xi'an 710072China

A type of novel electrospun supramolecular hybrid microfibers comprising poly(9-(4-(octyloxy)-phenyl)-2,7-fluoren-9-ol)(PPFOH)and poly(A/-vinylcarbazole)(PVK)are successfully prepared for intriguing multi-color emission *** supramolecular tunable PPFOH aggregation in PVK matrix endows the complex with a smart energy transfer behavior to obtain the multi-color *** stark contrast to PVK fibers,the emission color of PPFOH/PVK fibers with an efficient dispersion of PPFOH fluorophores at a proper dope ratio can be tuned in a wide spectrum of blue(0.1%),sky blue(0.5%),nearly white(1%),cyan(2%),green(5%)and yellow(10%).Besides,conductive behaviors of the microfiber were demonstrated in accompany with the increment of the doping ratio of PPFOH to *** fabrication of polymer light-emitting diode(PLED)based on the blended electrospun fiber provided a further evidence of its excellent electrical property for potential applications in optoelectronic devices.

关键词： Supramolecular approach Electrospinningπ-conjugated fibers Multi-color emissions Conductivity Polymer light-emitting diodes

Matrix Effect on Polydiarylfluorenes Electrospun Hybrid Microfibers: From Morphology Tuning to High Explosive Detection Efficiency

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Chinese Journal of Polymer Science 2023年第7期41卷 1011-1017页

作者： Wei Xue Man Xu Chuan-Xin Wei Hua-Min Sun Li-Li Sun Sheng-Jie Wang Jin-Yi Lin Nai-En Shi ling-hai xie Wei Huang State Key Laboratory of Organic Electronics and Information Displays&Institute of Advanced Materials(IAM) Nanjing University of Posts&TelecommunicationsNanjing210023China Center for Supramolecular Optoelectronics(CSO) Key Laboratory of Flexible Electronics(KLOFE)and Institute of Advanced Materials(IAM)Nanjing Tech University(NanjingTech)Nanjing211816China Frontiers Science Center for Flexible Electronics(FSCFE) Shaanxi Institute of Flexible Electronics(SIFE)&Shaanxi Institute of Biomedical Materials and Engineering(SIBME)Northwestern Polytechnical University(NPU)Xi’an710072China

Precisely optimizing the morphology of functional hybrid polymeric systems is crucial to improve its photophysical property and further extend their optoelectronic applications. The physic-chemical property of polymeric matrix in electrospinning (ES) processing is a key factor to dominate the condensed structure of these hybrid microstructures and further improve its functionality. Herein, we set a flexible poly(ethylene oxide) (PEO) as the matrix to obtain a series of polydiarylfluorenes (including PHDPF, PODPF and PNDPF) electrospun hybrid microfibers with a robust deep-blue emission. Significantly different from the rough morphology of their poly(N-vinylcarbazole) (PVK) ES hybrid fibers, polydiarylfluorenes/PEO ES fibers showed a smooth morphology and small size with a diameter of 1∼2 µm. Besides, there is a relatively weak phase separation under rapid solvent evaporation during the ES processing, associated with the hydrogen-bonded-assisted network of PEO in ES fibers. These relative “homogeneous” ES fibers present efficient deep-blue emission (PLQY>50%), due to weak interchain aggregation. More interestingly, low fraction of planar (β) conformation appears in the uniform PODPF/PEO ES fibers, induced by the external traction force in ES processing. Meanwhile, PNDPF/PEO ES fibers present a highest sensitivity than those of other ES fibers, associated with the smallest diameter and large surface area. Finally, compared to PODPF/PVK fibers and PODPF/PEO amorphous ES fibers, PODPF/PEO ES fibers obtained from DCE solution exhibit an excellent quenching behavior toward a saturated DNT vapor, mainly due to the synergistic effect of small size, weak separation, β-conformation formation and high deep-blue emission efficiency.

关键词： Matrix effect Electrospun fibers Polydiarylfluorenes Planar conformation Explosive detection

“Steric Armor”Strategy of Blue Fluorescent Emitters against Photooxidation-Induced Degradation

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Chinese Journal of Chemistry 2024年第11期42卷 1223-1229页

作者： Sha-Sha Wang Jing-Rui Zhang Kuan-De Wang Hao-Ran Li Peng-Hui Meng Yang Zhou Xiang Yu Ying Wei Quan-You Feng Yu-He Kan ling-hai xie Centre for Molecular Systems and Organic Devices(CMSOD) State Key Laboratory of Organic Electronics and Information Displays&Institute of Advanced MaterialsJiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing University of Posts&TelecommunicationsNanjingJiangsu210023 China Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials School of Chemistry and Chemical EngineeringHuaiyin Normal UniversityHuai'anJiangsu223300 China

Stability against oxygen is an important factor affecting the performance of organic semiconductor *** photooxidation stability can prolong the service life of the device and maintain the mechanical and photoelectric properties of the ***,various encapsulation methods from molecular structure to macroscopic device level are used to improve photooxidation ***,we adopted a crystallization strategy to allow 14H-spiro[dibenzo[c,h]acridine-7,9′-fluorene](SFDBA)to pack tightly to resist fluorescence decay caused by *** this case,the inert group of SFDBA acts as a“steric armor”,protecting the photosensitive group from being attacked by ***,compared with the fluorescence quenching of SFDBA powder under 2 h of sunlight,SFDBA crystal can maintain its fluorescence emission for more than 8 h under the same ***,the photoluminescence quantum yields(PLQYs)of the crystalline film is 327%higher than that of the amorphous *** shows that the crystallization strategy is an effective method to resist oxidation.

关键词： Organic semiconductor Photooxidation Spirocyclic aromatic hydrocarbons Crystal engineering Fluorescence

Theoretical Studies on Novel Gridspiroarenes: Structures, Noncovalent Interactions and Reorganization Energies

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Chinese Journal of Chemistry 2019年第9期37卷 915-921页

作者： Lei Yang Cheng-Zhu Yin Mohamad Akbar Ali Chao-Yang Dong Xin-Miao xie Xiang-Ping Wu Jie Mao Yong-Xia Wang Yang Yu ling-hai xie Lin-Yi Bian Jian-Min Bao Xue-Qin Ran Wei Huang Centre for Molecular Systems and Organic Devices(CMSOD) Key Laboratory for Organic Electronics and Information Displays & Jiangsu Key Laboratory for BiosensorsInstitute of Advanced Materials(IAM)Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing University of Posts & Telecommunications9 Wenyuan RoadNanjingJiangsu 210023China Department of Chemistry College of Science King Faisal UniversityAl-Ahsa31982Kingdom of Saudi Arabia Key Laboratory of Flexible Electronics(KLOFE)& Institute of Advanced Material(IAM) Jiangsu National Synergetic Innovation Center for Advanced Material(SICAM)Nanjing Tech University(Nanjing Tech)30 South Puzhu RoadNanjingJiangsu 211816China Shaanxi Institute of Flexible Electronics(SIFE) Northwestern Polytechnical University(NPU)127 West Youyi RoadXi'anShaanxi 710072China

Organic semiconductor materials with low reorganization energy have various applications such as in organic light-emitting diodes (OLEDs),organic field-effect transistor (OFETs) and organic solar cells (OSCs).In this work,we have designed a new class of gridspiroarenes (GS-SFX and GS-SITF) with #-shaped structures,which have novel crisscross geometrical structures compared to widely used spirocyclic arenes-SFX and *** structure electronic properties,adiabatic ionization potentials (IPa),adiabatic electron affinities (EAa) and reorganization energies (λ) of GS-SFX and GS-SITF have been calculated using density functional theory (DFT) *** calculated HOMO and LUMO spatial distributions suggest that GS-SFX and GS-SITF have better transport *** noncovalent interaction analysis shows the weak intramolecular interactions between their *** results indicate that the reorganization energies of GS-SFX and GS-SITF are significantly reduced compared to the dimer structures-DSFX and ***,the GS-SITF1 which is one of the isomers of GS-SITF exhibits the lowest values for λ(h)(0.067 eV) and λ(e)(0.153 eV).Therefore,we believe the predicted structure,electronic property,and reorganization energy are good indicator for transport *** work has systematically studied the effect of gridization,which provides insights to design organic semiconductor materials with excellent charge transport properties.

关键词： organic light-emitting diodes (OLEDs) organic field-effect transistor (OFETs) organic solar cells (OSCs)