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Suppressing the Undesirable Energy Loss in SolutionProcessed Hyperfluorescent OLEDs Employing bodipy-Based Hybridized Local and ChargeTransfer Emitter

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Energy & Environmental Materials 2024年第2期7卷 376-384页

作者： Xuewei Nie Zafar Mahmood Denghui Liu Mengke Li Dehua Hu Wencheng Chen Longjiang Xing Shijian Su Yanping Huo Shaomin Ji School of Chemical Engineering and Light Industry Guangdong University of Technology State Key Laboratory of Luminescent Materials and Devices and Institute of Polymer Optoelectronic Materials and Devices South China University of Technology

Hyperfluorescent organic light-emitting diodes（HF-OLEDs） approach has made it possible to achieve excellent device performance and color purity with low roll-off using noble-metal-free pure organic emitter. Despite significant progress, the performance of HF-OLEDs is still unsatisfactory due to the existence of a competitive dexter energy transfer（DET） pathway. In this contribution, two boron dipyrromethene（bodipy）-based donor-acceptor emitters（BDP-C-Cz and BDP-N-Cz） with hybridized local and charge transfer characteristics（HLCT） are introduced in the HF-OLED to suppress the exciton loss by dexter mechanism, and a breakthrough performance with low-efficiency roll-off（0.3%） even at high brightness(1000 cd m-2) is achieved. It is demonstrated that the energy loss via the DET channel can be suppressed in HF-OLEDs utilizing the HLCT emitter, as the excitons from the dark triplet state of such emitters are funneled to its emissive singlet state following the hot-exciton mechanism. The developed HF-OLED device has realized a good maximum external quantum efficiency（EQE） of 19.25% at brightness of1000 cd m-2and maximum luminance over 60 000 cd m-2, with an emission peak at 602 nm and Commission International de L'Eclairage（CIE） coordinates（0.57, 0.41）, which is among the best-achieved results in solution-processed HFOLEDs. This work presents a viable methodology to suppress energy loss and achieve high performance in the HF-OLEDs.

关键词： bodipy hyperfluorescence organic light-emitting diodes solution-process

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Cisplatin-appended bodipy for near infraredⅡfluorescent and photoacoustic imaging-guided synergistic phototherapy and chemotherapy of cancer

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Chinese Chemical Letters 2024年第3期35卷 352-357页

作者： Xuejian Xing E Pang Shaojing Zhao Tangna Pan Qiuxia Tan Benhua Wang Xiangzhi Song Minhuan Lan Key Laboratory of Hunan Province for Water Environment and Agriculture Product Safety College of Chemistry and Chemical EngineeringCentral South UniversityChangsha 410083China

Combining phototherapy and chemotherapy has been considered a promising modality for cancer therapy due to their synergistic ***,we developed three D-π-A-structured boron dipyrromethenes(bodipys)(named as B-B,B-C,and B-C-Pt).Due to their enlargedπ-conjugated structure and high intramolecular charge transfer effect,the synthesized bodipys had photothermal conversion capability,and their absorption and fluorescence spectra were *** cisplatin-appended bodipy(B-C-Pt)exhibited good singlet oxygen(^1O_(2))generation ability and near infrared(NIR)absorption and fluorescence(λ_(Abs)=748 nm,λ_(Em)=947 nm).After being encapsulated by distearoyl phosphoethanolamine polyethyleneglycol 2000(DSPE-PEG-2000),which could inhibit the H-aggregation of B-C-Pt,the absorption and fluorescence of the obtained B-C-Pt nanoparticles(NPs)were red-shifted to 762 and 985 nm,***^1O_(2)quantum yield and photothermal conversion efficiency of the B-C-Pt NPs were 4.0%and 40.6%,***,B-C-Pt NPs had chemotherapeutic efficacy due to the presence of *** vitro and in vivo studies further demonstrated that B-C-Pt NPs had synergistic therapeutic ***,B-C-Pt NPs could be employed in NIRⅡfluorescent and photoacoustic imaging-guided synergistic phototherapy and chemotherapy for cancer treatment.

关键词： Phototherapy Chemotherapy Cisplatin bodipy NIRⅡfluorescent imaging

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Acceptor Engineering Produces Ultrafast Nonradiative Decay in NIR-Ⅱ Aza-bodipy Nanoparticles for Efficient Osteosarcoma Photothermal Therapy via Concurrent Apoptosis and Pyroptosis

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Research 2024年第1期2024卷 625-635页

作者： Zhenxiong Shi Hua Bai Jiaxing Wu Xiaofei Miao Jia Gao Xianning Xu Yi Liu Jiamin Jiang Jiaqi Yang Jiaxin Zhang Tao Shao Bo Peng Huili Ma Dan Zhu Guojing Chen Wenbo Hu Lin Li Wei Huang Frontiers Science Center for Flexible Electronics Xi’an Institute of Flexible Electronics(IFE)and Xi’an Institute of Biomedical Materials&EngineeringNorthwestern Polytechnical UniversityXi’an 710072China Key Laboratory for Organic Electronics and Information Displays&Institute of Advanced Materials(IAM) Nanjing University of Posts&TelecommunicationsNanjing 210023China Key Laboratory of Flexible Electronics(KLOFE)and IAM Nanjing Tech UniversityNanjing 211800China Britton Chance Center for Biomedical Photonics-MoE Key Laboratory for Biomedical Photonics Wuhan National Laboratory for Optoelectronics-Advanced Biomedical Imaging FacilityHuazhong University of Science and TechnologyWuhan 430074China Department of Orthopedics Xijing HospitalThe Fourth Military Medical UniversityXi’an 710032China The Institute of Flexible Electronics(IFE Future Technologies)Xiamen UniversityXiamen 361005China

Small-molecule photothermal agents(PTAs)with intense second near-infrared(NIR-Ⅱ,1,000 to 1,700 nm)absorption and high photothermal conversion efficiencies(PCEs)are promising candidates for treating deep-seated tumors such as *** date,the development of small-molecule NIR-Ⅱ PTAs has largely relied on fabricating donor–acceptor–donor(D–A–D/D′)structures and limited success has been ***,through acceptor engineering,a donor–acceptor–acceptor(D–A–A′)-structured NIR-Ⅱ aza-boron-dipyrromethene(aza-bodipy)PTA(SW8)was readily developed for the 1,064-nm laser-mediated phototheranostic treatment of *** the donor groups to acceptor groups produced remarkable red-shifts of absorption maximums from first near-infrared(NIR-Ⅰ)regions(~808 nm)to NIR-Ⅱ ones(~1,064 nm)for aza-bodipys(SW1 to SW8).Furthermore,SW8 self-assembled into nanoparticles(SW8@NPs)with intense NIR-Ⅱ absorption and an ultrahigh PCE(75%,1,064 nm).This ultrahigh PCE primarily originated from an additional nonradiative decay pathway,which showed a 100-fold enhanced decay rate compared to that shown by conventional pathways such as internal conversion and vibrational ***,SW8@NPs performed highly efficient 1,064-nm laser-mediated NIR-Ⅱ photothermal therapy of osteosarcoma via concurrent apoptosis and *** work not only illustrates a remote approach for treating deep-seated tumors with high spatiotemporal control but also provides a new strategy for building high-performance small-molecule NIR-Ⅱ PTAs.

关键词： donor bodipy intense

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含吡咯杂环稠并bodipy的合成与性质研究

含吡咯杂环稠并BODIPY的合成与性质研究

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作者：付小凡烟台大学

学位级别：硕士

近年来随着现代科学的发展,具有特定功能的荧光染料在许多领域有着广泛应用。有机荧光染料因其结构和性质的可修饰性,相较于一些无机荧光染料有着更好应用和发展。其中氟硼二吡咯甲川（bodipy）作为一种新型的有机荧光染料,具有荧光量... 详细信息

近年来随着现代科学的发展,具有特定功能的荧光染料在许多领域有着广泛应用。有机荧光染料因其结构和性质的可修饰性,相较于一些无机荧光染料有着更好应用和发展。其中氟硼二吡咯甲川（bodipy）作为一种新型的有机荧光染料,具有荧光量子产率高以及光稳定性强等优点,在离子检测、生物标记、荧光传感以及光动力治疗（PDT）等方面有着广泛的应用。但bodipy母体的吸收和发射波长位于可见光区,细胞穿透性低,限制了bodipy在生物医学领域的应用,因此需要对bodipy母核进行修饰,将其吸收和发射波长红移至近红外光区。bodipy母核的修饰方法主要包括卤代、氮杂、芳环取代以及芳环稠并等,其中芳环稠并策略不仅可以延伸分子的共轭体系,还可以提升分子结构刚性。本文通过预官能团化的方式,成功构建了多种含吡咯杂环稠并bodipy分子,并探索了其光物理性质和生物应用。具体研究内容如下:（1）对称型双苯并噻吩稠并bodipy的合成与性质研究利用噻吩[3,2-g]吲哚前体为起始原料,合成了一系列对称型双苯并噻吩稠并bodipy（BTB）,并对其晶体结构、光物理和电化学性质以及PDT活性进行了研究。结果表明,这些新制备的BTB染料最大吸收波长位于643-665 nm范围内,且具有摩尔消光系数大以及单线态氧生成率高等优异性能。理论计算证实,较小的单重态-三重态能隙和较大的自旋轨道耦合导致了高效的系间窜越,从而提高了单线态氧量子产率。通过EPR实验确定该系列化合物在光激发下主要通过能量转移途径产生1O2。值得注意的是,Me2NPh-取代的BTB 1d的活性氧生成效率达到了41%,在He La细胞中表现出可忽略的暗毒性和显著的光毒性(IC50=83.5 n M),具有低剂量光动力治疗的潜力。（2）非对称型苯并噻吩稠并bodipy的合成与性质研究以噻吩[3,2-g]吲哚为前体合成了一系列具有不同取代基的非对称型苯并噻吩稠并bodipy（BTB）,对其晶体结构、光物理和电化学性质、脂滴成像以及PDT活性进行了研究。研究发现,该系列化合物最大吸收和发射波长范围在560-660 nm和620-700 nm之间。与对称型BTB不同的是,非对称型BTB具有更高的荧光量子产率,同时其在空气饱和甲苯中的活性氧生成效率最高达到50%。EPR实验证实,该系列化合物的高效ISC导致在光激发下同时生成1O2和O2-·。更重要的是,4-甲氧基苯乙烯基修饰的BTB 11h在He La细胞中展示出极高的光毒性,IC50值低至2.78n M,而其暗毒性极低（>10μM）。结果表明,在不对称苯并噻吩稠并bodipy平台α-位引入给电子基团,这可能是开发用于精密癌症治疗的长波吸收无重原子光敏剂的有效途径。（3）咔唑稠并bodipy的合成与性质研究以市售的咔唑为基本原料,成功合成出一系列咔唑稠并吡咯前体,进而合成一系列咔唑稠并bodipy分子,并对该系列化合物进行了结构表征和初步的光物理性质研究。研究发现该系列bodipy分子在六种常见溶剂中均具有良好的吸收和发射波长,其中最大吸收波长可达692 nm,最大发射波长可达753 nm,Stokes位移可达76 nm。摩尔消光系数也较大,最大可达146000 M-1cm-1。测量发现,随着溶剂极性的增加,所有bodipy分子吸收波长逐渐蓝移而发射波长逐渐红移。总结:本论文通过芳环稠并的方式成功合成出了一系列具有优良光物理性质的bodipy分子,并探索了其光物理性质以及生物应用。研究发现,该系列分子的吸收和发射波长均位于近红外区域,单线态氧产率较高,细胞实验证明,部分bodipy分子具有高光毒性和低暗毒性,有作为光敏剂用于PDT的潜力。

关键词： bodipy 噻吩[3,2-g]吲哚苯并噻吩咔唑近红外荧光染料细胞成像,光动力治疗

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Fluorescence Sensing of Glutathione Thiyl Radical by bodipy-Modified β-Cyclodextrin

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Chinese Journal of Chemistry 2022年第4期40卷 493-499页

作者： Zhixue Liu Xianyin Dai Qiaoyan Xu Xiaohan Sun Yu Liu College of Chemistry State Key Laboratory of Elemento-Organic ChemistryNankai UniversityTianjin 300071China

Comprehensive Summary The fluorescence sensing of intracellular glutathione thiyl radical(GS·)is in great demand to seek the GS·-related pathophysiological ***,boron-dipyrromethene(bodipy)-modified β-cyclodextrin was developed for high-efficiency sensing of GS·,accompanied by a fast response time(t_(1/2)=218 s),with the detection limit of 468 nmol/*** experiments indicated that the bodipy-modified p-cyclodextrin could be applied to detect the GS· in live A549 cells.

关键词： Cyclodextrins Glutathione thiyl radical Biosensors bodipy Radical reaction

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A bodipy-modified polymeric micelle for sustaining enhanced photodynamic therapy

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Chinese Chemical Letters 2022年第6期33卷 3277-3280页

作者： Yun-Chang Zhang Lan She Zi-Yue Xu Ze-Kun Wang Zhiqiang Ma Feng Yang Zhan-Ting Li Department of Inorganic Chemistry School of PharmacyNaval Medical UniversityShanghai 200433China Department of Chemistry Shanghai Key Laboratory of Molecular Catalysis and Innovative MaterialsFudan UniversityShanghai 200438China

Photodynamic therapy(PDT) has been gaining popularity in both scientific research and clinic applications due to its non-invasiveness and spatiotemporal targeting properties. Nevertheless, the local hypoxic microenvironment in tumor tissue impedes PDT universality. To overcome this drawback, a 2-pyridonebearing bodipy photosensitizer was synthesized rationally and introduced to polyethyleneglycol-bpoly(aspartic acid) to form a photosensitizer-^(1)O_(2) generation, storage/release agent dual-loading system(PEG-b-PAsp-bodipy). The investigation of the PDT effect at different illumination conditions in vitro and in vivo revealed that the system tremendously inhibited tumor proliferation, indicating that this new PEG-b-PAsp-bodipy could act as a potentially effective photo therapeutic system for cancer therapeutics.

关键词： Photodynamic therapy Polymeric micelle bodipy 2-Pyridone Tumor

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Hantzsch Ester Modified Asymmetric bodipy Probe with Ultra-high Sensitivity for Ultra-fast Detection of Endogenous Hypochlorite in Living Cells

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Chinese Journal of Chemistry 2023年第23期41卷 3319-3325页

作者： Tianli Zhu Mengting Zhao Rongcheng Wang Chenjun Dong Xuemei Dong Jie Sun Lixin Sun Chunchang Zhao Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center Institute of Fine ChemicalsSchool of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai200237 China

Hypochlorite(ClO^(-))is an important reactive oxygen species produced by the immune system to fight off invading pathogens,but its over-expression can interfere with normal physiological process and induce serious *** a variety of molecular probes have been reported for detecting ClO^(-),the development of advanced fluorescent tools with faster response and higher sensitivity to precisely monitor ClO^(-)remains a *** this work,two Hantzsch ester(a derivative of 1,4-dihydropyridine)derived fluorescent probes MeDHP-BCl and MeDHP-PhBCl were constructed based on asymmetric *** probes exhibit significant fluorescence turn-on in the ultra-sensitive(detection limit<1 nmol/L)and ultra-fast response(≤5 s)to ClO^(-).The reaction has been determined to be a highly selective N-chlorination of Hantzsch ester which cannot be activated by various common bioactive species,including nitric oxide(NO)that could oxidize Hantzsch ester under aerobic physiological conditions in most ***-PhBCl possessed a relatively longer fluorescence emission wavelength and higher quantum yield after activation,while more notably,MeDHP-BCl displayed lower cytotoxicity and more remarkable fluorescence increment in the response to ClO^(-),enabling selective and precise visualization of endogenous ClO^(-)over-expression in living RAW264.7 cells.

关键词： Hypochlorite Hantzsch ester bodipy Fluorescent probes Fluorescence spectroscopy Biomarkers Biosensors Bioimaging

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Aggregation Turns bodipy Fluorophores into Photosensitizers:Reversibly Switching Intersystem Crossing On and Off for Smart Photodynamic Therapy

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CCS Chemistry 2022年第11期4卷 3516-3528页

作者： Yan-Fei Kang Wen-Kai Chen Kun-Xu Teng Ling-Yun Wang Xiao-Cheng Xu Li-Ya Niu Ganglong Cui Qing-Zheng Yang College of Chemistry Beijing Normal UniversityBeijing 100875 College of LaboratoryMedicine Hebei North UniversityZhangjiakou075000 Hebei

We report for the first time a practical and simple supramolecular approach to turn fluorophores into photosensitizers(PSs).Using boron dipyrromethene(bodipy)as a proof-of-concept,eight bodipy derivatives manifest bright fluorescence and generate negligible singlet oxygen in *** contrast,aggregation fails to emit fluorescence and enhances singlet oxygen ***,these aggregates have excellent photodynamic therapy(PDT)performance,and one even exhibits much stronger photocytotoxicity than the commercialized PS Ce6 under identical *** studies show that this property originated from significantly reduced energy gaps between relevant excited singlet and triplet states,leading to considerably improved intersystem-crossing ***,a simple disaggregation recovers the original properties of the *** reversible switching property between fluorophores and PSs assists the development of smart PDT systems,in which singlet oxygen generation in tumors can be controlled in an intelligent manner after PDT *** present work provides a novel strategy to design heavy-atom-free PSs and may pave the way to the development of smart PDT systems.

关键词： photosensitizer aggregation bodipy photodynamic therapy intersystem crossing

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bodipy@Ir(Ⅲ)Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy

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Chinese Journal of Polymer Science 2018年第3期36卷 417-424页

作者： Yang Liu Nan Song Li Chen Zhi-Gang Xie Department of Chemistry Northeast Normal UniversityChangchun 130024China State Key Laboratory of Polymer Physics and Chemistry Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China

We present a new cyclometalated Ir（III） complexes IrBDP, which could self-assemble into organic nanoparticles （IrBDP NPs）. IrBDP NPs show enhanced photodynamic effect and can be engulfed by HeLa cells for cell ima... 详细信息

关键词： bodipy Photodynamic therapy Iridium complex

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bodipy-derived ratiometric fluorescent sensors: pH-regulated aggregation-induced emission and imaging application in cellular acidification triggered by crystalline silica exposure

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Science China Chemistry 2018年第11期61卷 1413-1422页

作者： Yang Bai Danyang Liu Zhong Han Yuncong Chen Zhongyan Chen Yang Jiao Weijiang He Zijian Guo State Key Laboratory of Coordination Chemistry Coordination Chemistry Institute School of Chemistry and Chemical EngineeringNanjing University

Modification of classic fluorophore to possess the emission transitions between aggregation-induced emission （ALE） and intrinsic emission offers reliable approach to the design of ratiometric fluorescent sensors. In this study, a proton acceptor benzimidazole was integrated with bodipy to form three compounds, BBI-1/2/3, which demonstrated the AIE （-595 nm, Iagg） in neutral aqueous medium and intrinsic bodipy emission （-510 nm,Iint） in acidic medium. All the three showed the ratiometric pH sensing behavior in a dual excitation/dual emission mode, yet BBI-3 displayed still the dual emission ratiometric pH sensing ability. The pH-dependent emission ratio/int/Iagg of the three were fully reversible, and no interference was observed from normal abundant chemical species in live cells. Their different pKa （BBI-1, pKa 4.4; BBI-2, pKa 2.7; BBI-3, pKa 3.6） suggested that the substituents on benzimidazole moiety were essential to govern their functioning pH range. The ratiometric imaging of BBI-1 in A549 cells provided an effective intracellular pH （pHi） calibration formula corresponding to emission ratio oflJ Iint/Iagg. Ratiometric pH imaging in A549 cells upon small particle exposure confirmed the particle-induced cellular acidification with this formula. Both particle size and the chemical nature of the particle contribute to the observed acidification effect. The synchronization of lysosome disruption to cellular acidification in A549 cells upon crystalline silica exposure was directly observed for the first time with BBI-1, showing the potential application of BBI-1 in the study of silicosis and other related diseases. This study de- monstrated that endowing fluorophore with AIE/intrinsic emission transition could be a promising strategy for ratiometric sensor design.

关键词： fluorescence imaging sensor cellular acidification aggregation-induced emission crystalline silica lysosome bodipy

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