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Self-assembly into Polymorphic 2D Nanosheets with Crystallization-Induced Emission Enhancement

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Chinese Journal of Chemistry 2022年第7期40卷 832-837页

作者： He Zhang Dong Jin Dongqing Lin Lei Huang Jin Wang Shasha Wang Linghai Xie Centre for Molecular Systems and Organic Devices(CMSOD) Key Laboratory for Organic Electronics and Information Displays&Institute of Advanced MaterialsJiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing University of Posts&TelecommunicationsNanjingJiangsu 210023China

Organic micro/nanocrystals with polymorphic tailorability and perfect platform to modulate decode the complex relationship among molecular structures,supramolecular/noncovalent interactions,aggregates and exciton behaviors.Herein,we precisely tune the polymorphic two-dimensional organic nanosheets(2DONs)of cyano-spirocyclic aromatic hydrocarbon(2'-CN-SFX),where the crystal growth processes are dominated by precursor concentration.The low concentration(ca.2 mmol/L)affords the rhombus-like nanosheets with monoclinic P21/c space group,in which molecules adopt antiparallel and slipped stacking mode.In contrast,the high concentration(ca.4 mmol/L)favors herringbone-like molecular packing pattern and then generates shuttle-like nanosheets with monoclinic C2/c space group.Both above polymorphic nanosheets exhibit unprecedented crystallization-induced emission en-hancement(CIEE)feature that increases the photoluminescence quantum yields(PLQYs)from 16%in solution,21%in amorphous film to 37%-39%in crystalline states.This result will offer promising opportunities for nanophotonics and organic intelligent semi-conductors.

关键词： Polymorphism Self-assembly 2D nanostructures Steric design Crystallization-induced emission enhancement Supramolecular chemistry

Nanogridarene:A Rising Nanomolecular Integration Platform of Organic Intelligence

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Chinese Journal of Chemistry 2020年第1期38卷 103-105页

作者： Xinmiao xie Ying Wei Dongqing Lin Chunxiao Zhong Linghai Xie 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)Nanjing University of Posts&Telecommunications9 Wenyuan RoadNanjingJiangsu 210023China Shaanxi Institute of Flexible Electronics(SIFE) Northwestern Polytechnical University(NPU)127 West Youyi RoadXi'anShaanxi 710072China

In the background of organic electronics,nanogridarenes with the criteria of well-defined edge and extendable vertexes were discovered toward chemical intellibots in 2014.Herein,Friedel-Crafts Gridization(FCG)as the molecular installing technology(MIT)will be highlighted to synthesize various monogrids,multigrids and polygrids that would be potential cornerstone of covalent window,molecular integration and circuit as well as organic robots.

关键词： corners vertex synthesize

Novel Porphyrin-Containing Polymer Based Memristor for Synaptic Plasticity Simulation

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Chinese Journal of Chemistry 2022年第20期40卷 2451-2456页

作者： Linyi Bian Meng xie Hao Chong Zhewei Zhang Guangyi Liu Qiushuo Han Jiaoyang Ge Zheng Liu Yang Lei Guangwei Zhang Linghai Xie Centre for Molecular Systems and Organic Devices State Key Laboratory of Organic Electronics and Information DisplaysJiangsu Key Laboratory for BiosensorsInstitute of Advanced MaterialsNanjing University of Posts&Telecommunications9 Wenyuan RoadNanjingJiangsu210023 China

The porphyrin-based copolymer PZnTPP-SFX is designed and synthesized by alternating porphyrin and spiro[fluorene-9,9'-xanthene]via Suzuki copolymerization.A simple memristor structure of ITO/ZnTPP-SFX/AlOx/Al was fabricated by spin-coating process.The conventional synaptic plasticity is emulated using the single memristor including nonlinear transmission characteristics,spike-timing dependent plasticity and spike-rate dependent plasticity.New spike-voltage dependent plasticity is also found in the memristor which can selectively perform potentiation and depression behaviors at a unipolar voltage.Compared with the device performance of uncoordinated metalloporphyrin polymer,it was found that oxygen vacancies diffuse and migrate into PZnTPP-SFX layer with the assist of coordination metal.This study suggests that porphyrin-based polymers have great promise for synaptic simulation of artificial neural network.

关键词： Copolymerization Spiro compounds Memristor Cooperative effects Synaptic plasticity

Toward Eco-friendly Green Organic Semiconductors： Recent Advances in Spiro[fluorene-9,9＇-xanthene] （SFX）-Based Optoelectronic Materials and Devices

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Chinese Journal of Chemistry 2015年第8期33卷 815-827页

作者： Mingli Sun Ruochen Xu Linghai Xie Ying Wei Wei Huang Center for Molecular Systems and Organic Devices Key Laboratory for Organic Electronics andlnormation Dis-plays & Institute of Advanced Materials National Synergistic Innovation Center for Advanced Materials Nanjing University of Posts & Telecommunications Nanjing Jiangsu 210023 China Department of Chemistry College of Science Northeast Forestry University Harbin Heilongfiang 150040 China Key Laboratory of Flexible Electronics & Institute of Advanced Materials National Synergistic Innovation Center for Advanced Materials Nanjing Tech University Nanjing Jiangsu 211816 China

Green organic semiconductors （GOS） have the four-element features, including biomass as stuffs, synthesis with the pot, atom and step economic （PASE） route, eco-friendly fabrication processes in aqueous phase, and recy- clable devices, capturing the trend of organic electronics in the future. Herein, we reviewed the efforts that have been made on GOS by our group. We first made a brief introduction of organic （opto）electronics, followed by the design strategies of GOSs based on spirofluorenes. Concretely, we described the discovery of one-pot protocol to spirofluorenres and a pot-atom-step economic （PASE） platform of spiro[fluorene-9,9＇-xanthene] （SFX） for the mo- lecular design of organic semiconductors, as well as a state-of-the-art nanocrystalline films with eco-friendly pro- cedures. Then, we highlighted the progress on SFX-based organic semiconductors in the organic light-emitting di- ode （OLED） field. Finally, we conducted a summary on SFXs in OLED and an outlook on green semiconductors starting from biomass, via one-pot to spirofluorenes, to water-phase devices.

关键词： spirofluorenes green semiconductors pot-atom-step economic nanocrystals organic light-emitting devices

Member of Editorial Board of Rising Stars

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Chinese Journal of Chemistry 2018年第6期36卷 562-562页

作者： Linghai Xie Professor Center for Molecular Systems & Organic Devices (CMSOD) Jiangsu Key Laboratory for Organic Electronics & information Displays (KLOEID) and Institute of Advanced Materials(IAM)Nanjing University of Posts and Telecommunications(NJUPT)

Hierarchical and Multiscale Chemistry of Organic Semiconductors ＆ Devices My research interest is organic electronics. The uncertainty evolution of molecular systems from solution to film is the key challenge for organic devices. We initiated the Hierarchical Chemistry for the rational design of organic polymer semiconductors and devices starting from the four-element principle （Figure, reference 3）. Until now, our contributions include one-pot tandem protocol of spiro[n]arenes, especially SFXs; supramolecular steric hindrance （SSH） effect and synergistically molecular attractor-repulsor theory （SMART） that is one rule to dominate aggregates under the noncovalent force; organic grid[n]arenes, including nanogrids and polygrids, that are independent on macrocycles, 3D cages, nanorings, frameworks （MOFs and COFs） as well as other closed molecules; organic multimedia with the function of molecular electron/ion semiconductors （MEIS） for the era of consciousness （EOC）.

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Universal 4-qualifiable fluorene-based building blocks for potential optoelectronic applications

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Chinese Chemical Letters 2022年第12期33卷 5137-5141页

作者： Xiang An Jinghao Yang Man Xu Lili Sun Lubing Bai Kai Wang Zhiqiang Zhuo Yingying Zheng Jinyi Lin Xuehua Ding Yuyu Liu Linghai Xie Chengrong Yin Wei Huang Key Laboratory of Flexible Electronics(KLOFE)&Institute of Advanced Materials(IAM) Nanjing Tech University(NanjingTech)Nanjing 211816China State Key Laboratory of Organic Electronics and Information Displays&Institute of Advanced Materials(IAM) Nanjing University of Posts&TelecommunicationsNanjing 210023China Frontiers Science Center for Flexible Electronics(FSCFE) MIIT Key Laboratory of Flexible Electronics(KLoFE)Northwestern Polytechnical UniversityXi'an 710072China Electrical Engineering College Nanjing Vocational University of Industry TechnologyNanjing 210023China

In the design of conjugated molecules,modular production enables materials to easily realize structure modification and precisely tune their photoelectrical property.Construction of a novel and universal building block is crucial to design and manufacture high performance and stable conjugated molecules for optoelectronic application.Herein,we originally demonstrated a universal 4-qualifiable fluorene-based building block,which is a fundamental molecular segment to functionalize and obtain novel conjugated materials.Compared to the traditional modification at 9-site,additional 4-position functionalization provided an exciting blueprint to not only tune electronic structure and excited state via p-n molecular design engineering and space charge-transfer strategy,but also allow for optimizing intermolecular arrangement and obtaining solution-processing ability.The introduction of the 4-site substituent in fluorene based semiconductors may endow materials with unique properties.Finally,we successfully prepared two stable deep-blue light-emitting conjugated polymer,PODOPF and PODOF,by utilizing the 4-substituent fluorene based building block.It is believable that the performance,stability and processibility of reported outstanding fluorene-based conjugated molecules can be further optimized based on this universal building block.

关键词： Side-chain coupling Small molecular emitter Morphological stability Deep-blue emission Optoelectronic device

Carbazole-endcapped Spiro[fluorene-9,9＇-xanthene] with Large Steric Hindrance as Hole-transporting Host for Heavily-doped and High Performance OLEDs

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Chinese Journal of Chemistry 2015年第8期33卷 955-960页

作者： Xianghua Zhao Yukun Wu Nannan Shi Xiaoyu Li Yi Zhao Mingli Sun Dongxue Ding Hui Xu Linghai Xie College of Chemistry and Chemical Engineering Xinyang Normal University Xinyang Henan 464000 China State Key Laboratory on Integrated Optoelectronics College of Electronics Science and Engineering Jilin University 2699 Qianjin Street Changchun Jilin 130012 China China Key Laboratory for Organic Electronics & Information Displays (KLOEID) Institute of Advanced Materials (IAM) Nanjing University of Posts & Telecommunications Nanjing Jiangsu 210046 China Key Laboratory of Functional Inorganic Material Chemistry Ministry of Education Heilongjiang University Harbin Heilongjiang 150080 China

In this work, we designed and synthesized a novel spirocyclic compound functionalized spiro[fluorene-9,9＇- xanthene] with carbazole group （2-carbazolyl-spiro[fluorene-9,9＇-xanthene], SFX-Cz） via Friedel-Crafts and Ullmann reaction, which is expected to own high thermal and morphological stability, and good carrier injection/ transporting properties due to the excellent hole transporting characteristics of carbazole and cruciform structure of spiro[fluorene-9,9＇-xanthene]. The carbazole end-capped spiro[fluorene-9,9＇-xanthene] SFX-Cz based PhOLEDs with Flrpic as phosphor emitter have been researched by varying dopant concentration, which exhibit the maximum EQEs of 8.9%, 7.4%, 9.1%, and 4.7% with the doping increasing from 10% to 50%. The higher performance PhOLEDs are independent on concentration variation from 10% to 30%, which suggests the bulky steric hindrance of SFX-Cz might be a potential canditate for high performance and inexpensive device with simplified process.

关键词： steric hindrance spirocyclic compound heavily-doped PhOLEDs inexpensive device

Promoting near-infrared II fluorescence efficiency by blocking long-range energy migration

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聚集体(英文) 2023年第3期4卷 102-109页

作者： Changjin Ou Lei An Ziqi Zhao Fan Gao Liangyu Zheng Chao Xu Kang Zhang Jinjun Shao Linghai Xie Xiaochen Dong Institute of Advanced Materials and Flexible Electronics(IAMFE) School of Chemistry and Materials ScienceNanjing University of Information Science and TechnologyNanjingChina State Key Laboratory of Organic Electronics and Information Displays and Institute of Advanced Materials Nanjing University of Posts and TelecommunicationsNanjingChina Key Laboratory of Flexible Electronics(KLOFE)and Institute of Advanced Materials(IAM) Nanjing Tech University(NanjingTech)NanjingChina School of Chemistry and Materials Science Jiangsu Normal UniversityXuzhouChina

Generally,long wavelength absorbed near-infrared II(NIR-II)dyes have a low fluorescence efficiency in aggregate states for aggregate-caused quenching effect,simultaneously enhancing efficiency and extending absorption is a challenging issue for NIR-II dyes.Here,three benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole(BBT)derivatives(TPA-BBT,FT-BBT,and BTBT-BBT)are used to clarify fluorescence quenching mechanisms.When the BBT derivatives are doped into a small molecule matrix,they show quite different fluorescence behaviors.Structuredistorted TPA-BBT displays fluorescence quenching originating from short-range exchange interaction,while FT-BBT and BTBT-BBT with a co-planar-conjugated backbone exhibit concentration-dependent quenching processes,namely changing from long-range dipole-dipole interaction to exchange interaction,which could be majorly ascribed to large spectral overlap between absorption and emission.By precisely tuning doping concentration,both FT-BBT and BTBT-BBT nanoparticles(NPs)present the optimal NIR-II fluorescence brightness at∼2.5 wt%doping concentration.The doped NPs have good biocompatibility and could be served as fluorescence contrast agents for vascular imaging with a high resolution under 980-nm laser excitation.Those paradigms evidence that molecular doping can promote fluorescence efficiency of long wavelength-absorbed NIR-II fluorophores via suppressing long-range energy migration.

关键词： co-planar structure dipole-dipole interaction fluorescence quenching molecular doping NIR-II fluorophore

Hierarchical structures,surface morphology and mechanical elasticity of lamellar crystals dominated by halogen effects

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中国化学快报:英文版 2023年第8期34卷 337-342页

作者： Chuanxin Wei Jianfeng Wang Yanni Zhang Xuehua Ding Yanze Jiang Qiang Zhao Jinyi Lin Jianfeng Zhao Linghai Xie Wei Huang Key Laboratory of Flexible Electronics(KLOFE) Institute of Advanced Materials(IAM)Nanjing Tech University(NanjingTech)Nanjing 211816China Key Laboratory for Organic Electronics and Information Displays Institute of Advanced Materials(IAM)Nanjing University of Posts&TelecommunicationsNanjing 210023China Institute of Flexible Electronics(IFE) Northwestern Polytechnical University(NPU)Xi’an 710072China

To understand the deformation mechanism of molecular crystals under mechanical forces will accelerate the molecular design and preparation of deformable crystals.Herein,the relationship between structural halogenation and molecular-level stacking,micro/nanoscale surface morphology,and macroscopic mechanical properties are investigated.Elastic crystals of halo-pyrimidinyl carbazoles(CzM-Cl,CzM-Br and CzM-I)with lamellar structure and brittle crystal(CzM-F)were quantitatively analyzed by crystal energy framework(CEF)providing the inter/intralayer interaction energy(Inter/Intra-IE).It is revealed that the elastic crystals bend under external force as a result from stronger Intra-IE to prevent cleavage and weaker Inter-IE for the short-range movement of molecules on the slip plane.This research will provide an insight for the molecular design of flexible crystals and facilitate the development of next-generation smart crystal materials.

关键词： Halogen Lamellar crystal Elasticity Crystal energy framework(CEF) Inter/intralayer interaction energy (Inter/Intra-IE)