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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

Structural modification of bodipy: Improve its applicability

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Chinese Chemical Letters 2019年第10期30卷 1815-1824页

作者： Mengdi Liu Siyue Ma Mengyao She Jiao Chen Zhaohui Wang Ping Liu Shengyong Zhang Jianli Li Ministry of Education Key Laboratory of Synthetic and Natural Functional Molecule Chemistry College of Chemistry & Materials Science Northwest University

bodipy has been considered a potential scaffold because of their neutral total charge, sharp absorption,and emission with high fluorescence quantum yield. However, the drawback of emission wavelength at less than 600 nm and hydrophobicity limit its application. One of the extremely interesting properties of bodipy is that small modifications to their structures could be able to tune their properties, mainly including the absorption/emission wavelength and the hydrophilicity. This review focuses on the modification at different positions of bodipy to improve the water-solubility and emission wavelength that describe their spectral, photophysical properties and applicability, which is helpful for the researchers to rationally design bodipy dyes to adapt a wide range of applications.

关键词： bodipy Near-infrared Water solubility Modification Application

Elucidating the excited-state dynamics behavior in near-infrared bodipy dye and aggregates toward biophotonics

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Science China Chemistry 2020年第8期63卷 1075-1081页

作者： Xiaofei Miao Haojie Tao Wenbo Hu Yonghui Pan Quli Fan Wei Huang Key Laboratory for Organic Electronics and Information Displays&Institute of Advanced Materials(IAM) Nanjing University of Posts&TelecommunicationsNanjing 210023China Shaanxi Institute of Flexible Electronics(SIFE) Northwestern Polytechnical University(NPU)Xi’an 710072China

Photo-induced excited-state dynamics within organic materials fundamentally determine their photophysical properties for various applications,and thus understanding the primary excited-state dynamics behavior is of fundamental and practical *** recently,the excited-state dynamics of organic materials towards biophotonics have been rarely studied,although numerous endeavors have been devoted to the design of organic materials for ***,various spectroscopy technologies including femtosecond transient absorption(fs-TA)spectroscopy clearly reveal a totally different excited state dynamics behavior within bodipy monomer(2B-BDP dye)and aggregates(2B-BDP NPs),indicating strongly morphology dependent character.2B-BDP dye undergoes an ultrafast conversion from S1 to intramolecular charge transfer(ICT)state for subsequent photoluminescence(PL)and nonradiative(NR)decay,while 2B-BDP NPs show an accelerated excited-state deactivation mainly through S1→S0 NR *** potential bioapplications based on the corresponding excited state dynamics behavior are discussed together with experimental ***,the accelerated NR decay in 2B-BDP NPs does not yield a stronger photoacoustic(PA)signal than that in 2B-BDP dye,which violates the conventional wisdom that faster NR decay would benefit the photothermal effects for better photoacoustic imaging(PAI).These insightful and fundamental observations of the excited-state dynamics may contribute an alternative approach at the molecular level towards the future design of functional bodipy-based organic molecules with desirable performances.

关键词： excited-state dynamics bodipy organic nanoparticles intramolecular charge transfer photoacoustic imaging

Synthesis,Characterization and Optical Properties of Poly(aryleneethynylene)s Containing bodipy

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Chinese Journal of Polymer Science 2015年第8期33卷 1133-1139页

作者： Bin Liu Fang-lin Huang Yong-feng Shi Zhi-qing Ni Ye Lin 尹守春 Hangzhou Science and Technology Information Institute College of Material Chemistry and Chemical Engineering Hangzhou Normal University

Poly（aryleneethynylene）s containing bodipy （4,4-difluoro-4-bora-3a,4a-diaza-s-indacene）（P 1） were prepared by palladium-catalyzed Sonogashira polymerization of 2,6-diiodo-functionalized bodipy monomer （M1） with 1,4-diethynyl- 2,5-didodecyl-oxybenzene monomer （M2）. The structures of the monomer （M1） and copolymer （P1） were confirmed by IH-NMR and Fourier transform infrared （FTIR） spectroscopies; their optical properties were characterized by UV-Vis absorption, photoluminescence （PL） spectroscopy and the Z-scan technique. Both UV-Vis absorption and fluorescence emission of copolymer P1 red-shifted to longer wavelengths （λabs： from 502 nm to 542 nm; 2era： from 511 nm to 631 nm） relative to those of the monomer M1 due to the π-conjugation extension of the copolymer. The third-order nonlinear optical coefficient （x^（3）） of copolymer P1 was 1.94 × 10^-10 esu, which is almost two or three orders of magnitude greater than that of common conjugated polymers without BODPIY moiety.

关键词： bodipy Conjugated polymers Nonlinear optics Synthesis.

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2023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

bodipy-based supramolecular fluorescent metallacages

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Chinese Chemical Letters 2023年第3期34卷 80-89页

作者： Yute Wang Yi Qin Xiaoli Zhao Peipei Jia Zhiyong Zeng Lin Xu Shanghai Key Laboratory of Green Chemistry and Chemical Processes Shanghai Frontiers Science Center of Molecule Intelligent SynthesesSchool of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China

During the past few years, the construction of bodipy-based supramolecular fluorescent metallacages through coordination-driven self-assembly has gained increasing interest due to their unique photophysical properties and applications in catalysis, sensing, and bioimaging. In consideration of the rapid development of this field, it is time to summarize recent developments involving bodipy-based *** this review, a comprehensive summary of the construction of bodipy-based metallacages as well as their photophysical properties and applications will be presented.

关键词： Metallacage bodipy Coordination-driven self-assembly Tetrahedron Fluorescence

A bodipy-based Fluorescent Probe for Thiophenol

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Chinese Journal of Chemistry 2018年第2期36卷 119-123页

作者： Dongxiang Zhang Ning Xu Liman Xian Haoying Ge Jiangli Fan Jianjun Du Xiaojun Peng State Key Laboratory of Fine Chemicals Dalian University of Technology Dalian 116024 China

Thiophenol has been listed as one of the main sources of pollution. Sensitive probes for thiophenol are very significant. Herein, a bodipy-based fluorescent probe, named BDP, for poisonous thiophenol detection has been reported. BDP shows rapid response （15 s） and clear fluorescence enhancement （30 folds） to thiophenol in solution. The intensity of fluorescence and concentration of thiophenol have a good linear relationship. The detection limit is as low as 13.6 nmol·L^-1： BDP is stable towards pH and light radiation. Cell experiments demonstrate that BDP has good cell membrane penetrability, low cell toxicity and excellent imaging properties in living cells. Therefore, BDP has significant value on the detection of thiophenol in solution and in living cell.

关键词： thiophenol bodipy fluorescent probe cell imaging

Intramolecular Charge Transfer-Enhanced bodipy Photosensitizer in Photoinduced Electron Transfer and Its Application to Photoxidation under Mild Condition

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Chinese Journal of Chemistry 2015年第11期33卷 1251-1258页

作者： Ruiqin Wang Ying Geng Lili Zhang Wenting Wu Weiyu Fan Zhongtao Li Lizhuo Wang Liying Zhan Xueyan Wu Mingbo Wu State Key Laboratory of Heavy Oil Processing School of Chemical Engineering China University of Petroleum Qingdao Shandong 266580 China ~cience and Techology Bureau of Huangdao Qingdao Shandong 266400 China

Photoinduced electron transfer process is a crucial step in photooxidation to obtain synthetic chemicals. How- ever, the driving forces of electron transfer as priority in all have been rarely studied in stepwise detail. Herein, we report a series of bodipy derivatives with an emphasis on the intramolecular charge transfer, enhancing the key step of photoinduced electron transfer process and photooxidation performances. A series of novel bodipy photosensitizers （B-1--B-5） were prepared, wherein diethylamine amino of B-3 as charge injection group was conjugated to the 2,6-diiodo-styryl-bodipy, and the electron transfer impetus was enhanced 1.6 times due to its more negative redox potentials. These results were also confirmed by the DFT/TDDFT calculation. Without pure oxygen, B-3 still can exhibit an exceptional performance in photoxidative aromatization of 1,4-DHP under mild condition. After irradiation for 28 rain, the conversion rate came to 98.2%.

关键词： intramolecular charge transfer photoinduced electron transfer bodipy photosensitizers photoxidation

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