ORGANIC & BIOMOLECULAR CHEMISTRY
·
2017
·Vol. 15
·期 28
·6006-6013
·
IF 3.564
Liangbin Lin,Xiaoru Lin,Hongyu Guo,Fafu Yang
This study focuses on the construction of novel diphenylacrylonitrile-connected BODIPY dyes with high fluorescence in both solution and an aggregated state by combining DRET and FRET processes in a single donor–acceptor system. The first BODIPY derivatives with one, two, or three AIE-active diphenylacrylonitrile groups were designed and synthesized in moderate yields. Strong fluorescence emissions were observed in the THF solution under excitation at the absorption wavelength of non-emissive diphenylacrylonitrile chromophores, implying the existence of the DRET process between the dark diphenylacrylonitrile donor and the emissive BODIPY acceptor. In the THF/H2O solution, the fluorescence intensity of the novel BODIPY derivatives gradually increased under excitation at the absorption wavelength of diphenylacrylonitrile chromophores, suggesting a FRET process between diphenylacrylonitrile and BODIPY moieties. A greater number of diphenylacrylonitrile units led to higher energy-transfer efficiencies. The pseudo-Stokes shift for both DRET and FRET processes was as large as 190 nm.
研究领域:
化学
·
材料科学
·
光学
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产品关联
DOI
PubMed
高影响因子
Journal of Materials Chemistry B
·
2021
·Vol. 9
·期 36
·7461-7471
·
IF 6.331
Juanjuan Yin,Xu Jiang,Guomin Sui,Yingying Du,Enyun Xing,Ruijie Shi,Chengzhi Gu,Xiaona Wen,Yaqing Feng,Zhongqiang Shan,Shuxian Meng
BODIPY dyes have recently been used for photothermal and photodynamic therapy of tumors. However, complex multi-material systems, multiple excitation wavelengths and the unclear relationship between BODIPY structures and their PTT/PDT efficiency are still major issues. In our study, nine novel BODIPY near-infrared dyes were designed and successfully synthesized and then, the relationships between BODIPY structures and their PTT/PDT efficiency were investigated in detail. The results showed that modifications at position 3,5 of the BODIPY core with conjugated structures have better effects on photothermal and photodynamic efficiency than the modifications at position 2,6 with halogen atoms. Density functional theory (DFT) calculations showed that this is mainly due to the extension of the conjugated chain and the photoinduced electron transfer (PET) effect. By encapsulating BDPX-M with amphiphilic DSPE-PEG2000-RGD and lecithin, the obtained NPs not only show good water solubility and biological stability, but also could act as superior agents for photothermal and photodynamic synergistic therapy of tumors. Finally, we obtained BODIPY NPs that exhibited excellent photothermal and photodynamic effects at the same time under single irradiation with an 808 nm laser (photothermal conversion efficiency: 42.76%, A/A0: ∼0.05). In conclusion, this work provides a direction to design and construct phototherapeutic nanoparticles based on BODIPY dyes for tumor treatment.
研究领域:
生物医学工程
·
药物化学
·
材料科学
✓ 已验证
DOI
高影响因子
ORGANIC ELECTRONICS
·
2023
·
IF 3.2
Bao Xie,Lunxiang Yin,Chang Liu,Junmei Fan,Xu Wang,Yanqin Li
Boron dipyrromethene (BODIPY) dyes have attracted great interests in organoboron chemistry because of their excellent photophysical and electrochemical properties . However, the power conversion efficiency (PCE) of BODIPY-based photovoltaic devices is still relatively low in organic small-molecule solar cells, so the design and development of new photovoltaic materials based on BODIPY have become particularly important by adjusting molecular energy level and bandgap. Recently, symmetrical “BODIPY-TPA” conjugated material gave a desirable electrochemical bandgap as low as 1.36 eV, which prompts us to systematically regulate molecular energy level and bandgap by finely optimizing the structure of reference material SM1 . Therefore, two series of BODIPY dyes were synthesized successfully by one-step Stille reaction . The first type is symmetric D-π-A-π-D-type molecules SM1 and SM3 , where electron-rich triphenylamine and carbazole groups (D) are located on two sides of electron-deficient BODIPY part (A) via thiophene π-spacer, respectively. The second type is unsymmetric D-π-A-type molecules SM2 and SM4 , constructed by removing one “π-D” segment from the symmetric structure. A synergetic effect of regulating terminal group and molecular skeleton length simultaneously on the optoelectronic properties of series of BODIPY dyes, are systematically investigated. As expected, all BODIPY dyes exhibit preferable electrochemical bandgaps of only 1.36–1.56 eV, suitable highest occupied molecular orbital (HOMO) energy levels (<-5.16 eV) and excellent thermal stability ( T d > 340 °C). On the one hand, unsymmetric molecules possess deeper HOMO energy level, whereas symmetric counterparts show enhanced and red-shifted absorption characteristics, ascribed to tunable molecular conjugation length. On the other hand, TPA-containing materials exhibit smaller electrochemical bandgaps, whereas CZ analogues possess lower HOMO energy levels, due to variable electron-rich character of D group. These BODIPY dyes with [6,6]-phenyl-C 61 -butyric acid methyl ester (PC 61 BM) acceptor material , are primarily fabricated to evaluate their photovoltaic properties. The devices based on SM2 and SM4 gave better PCEs of 4.33% and 3.27%, respectively, also yielding higher open-circuit voltages ( V oc s) of 0.87–0.89 V, relative to symmetric ones. In addition, CZ-based devices performed higher V oc than the corresponding TPA-based devices, mainly attributed to deeper HOMO energy level. This work emphasizes a synergetic design strategy of altering end-group structure and molecular main chain length, especially the design of unsymmetric organoboron coordination compounds, which provides important suggestions for enriching novel BODIPY optoelectronic materials.
研究领域:
有机化学
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材料科学
·
光电子学
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产品关联
DOI
高影响因子
DYES AND PIGMENTS
·
2023
·
IF 4.5
Xianjun Zhao,Bo Hu,Qun Zhou,Yijie Yu,Erhong Hao,Xing Guo,Yangyang Xu,Changjiang Yu,Ke Sun,Jacques Lalevée
Until now the photopolymerization process is largely dependent on the hazardous UV or near UV light irradiation. Herein this work, a series of boron dipyrromethene (BODIPY) derivatives substituted by electron-donating triphenylamine moiety on different positions were introduced and investigated thoroughly. Markedly, their photoinitiation abilities under mild conditions, e.g. visible LEDs irradiation and room temperature, were examined for the first time. In combination with an iodonium salt and an amine as the co-initiators, these BODIPY dyes could form three-component photoinitiating systems (PISs) for the purpose to initiate both the free radical polymerization of acrylate monomers and cationic polymerization of epoxy monomers. Interestingly, under the irradiation of LED@405 nm, LED@530 nm or LED@660 nm, some of these BODIPYs-based PISs could conduct high monomeric conversion and rapid photopolymerization rates, as reflected by the relevant photopolymerization kinetics. Then the notable photochemical reactivity of these BODIPY dyes was examined by both steady state photolysis and fluorescence quenching experiments, and theoretical calculation was also performed on them in details. Finally, photocuring 3D printing technique was applied to the acrylate/epoxy mixture resin, as the result the BODIPYs-based PISs demonstrated great potential to fabricate truly three-dimensional objects in macroscopic scale with excellent spatial resolution.
研究领域:
材料科学
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化学工程
·
光学工程
✓ 已验证
产品关联
DOI
高影响因子
TETRAHEDRON
·
2014
·
IF 2.817
Junchao Xu,Leiming Zhu,Qiusheng Wang,Lintao Zeng,Xichao Hu,Boqiao Fu,Zhe Sun
A series of meso -C 6 F 5 BODIYs have been successfully synthesized and characterized. Some of them displayed excellent spectroscopic properties, such as relatively large Stokes shift , high fluorescence quantum yield , far-red or near infrared region (NIR) emission, and good photostability. In particular, the dye functionalized with oligo(ethylene glycol) ether-phenyl groups at the 3,5-position of BODIPY core became water-soluble and its emission located in the NIR region with large Stokes shift. Time-dependent density functional theory calculations were conducted to understand the structure–optical properties relationship. Furthermore, cell staining tests demonstrated that the meso -C 6 F 5 BODPY derivative with oligo(ethylene glycol) ether-phenyl group was membrane permeable and selectively stained cytosol in living cells.
研究领域:
化学
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生物医学工程
·
细胞生物学
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产品关联
DOI
高影响因子
ANALYTICA CHIMICA ACTA
·
2022
·
IF 6.911
Jin-Ye Lu,Qiu-Yun Chen,Su-Ci Meng,Chang-Jian Feng
Phthalates can penetrate the environment and enrich various aquatic organisms through the food chain, which is involved in promoting the growth of breast cancer. It is of current interest to develop new sensors for phthalates. We herein reported a hydrogen-bond competing fluorescent sensor, BANP, for the detection of dibutyl phthalate (DBP). The BANP compound was synthesized by assembling andrographolide (Andro), nitro- and cyano-substituted BODIPY dye (BCN), and polyethylene glycol derivatives (DSPE-mPEG5000). BANP was found to be a turn-on fluorescent probe for DBP in water with a detection limit of 0.13 μg/g; the DBP-water system acts as a hydrogen bond switch to turn on the fluorescence. And BANP fluorescently detected DBP in contaminated fish meat. Moreover, BANP sensed the DBP-induced growth of human breast cancer MCF-7 cells, and the release of Andro in the DBP-cultivated cancer cells inhibited the proliferation of the MCF-7 cells. Taken together, BANP is a DBP-responsive probe for sensitive DBP detection in water, cells, and fish meats. The BANP sensor may be used in both in vitro fluorescence and cellular imaging analyses. Our results show that guest-induced reassembly brings forth significant fluorescence change, which is a promising way of designing new fluorescent probes for the analysis of phthalates in the environment and food.
研究领域:
分析化学
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环境科学
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生物医学
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产品关联
DOI
PubMed
高影响因子
ANALYST
·
2014
·Vol. 140
·期 2
·574-581
·
IF 3.906
Jian Xu,Shaobo Sun,Qian Li,Ying Yue,Yingdong Li,Shijun Shao
A novel “Turn-On” fluorescent probe, quaternarized 4-pyridinyl-substituted BODIPY dye by incorporating a 5-nitrofuran moiety, was developed and applied for imaging the hypoxic status of tumor cells by the indirect detection of nitroreductase. The design was based on a nitroreductase-catalyzed reduction of the nitrofuran moiety in the presence of reduced nicotinamide adenine dinucleotide (NADH) as an electron donor and followed by the 1,6-rearrangement-elimination and the release of free 4-pyridinyl-substituted BODIPY dye 2. This probe displayed desired properties such as high specificity, “Turn-On” fluorescence response with suitable sensitivity, appreciable water solubility and rapid response time (within 5 min). Moreover, as a biocompatible molecule, the probe has been successfully applied for imaging the hypoxic status of tumor cells (e.g. A549 cells) and especially used for real-time determination of nitroreductase produced by Escherichia coli. Therefore, we hope to apply this novel method in the biomedical research fields for the imaging of disease-relevant hypoxia and detection of pathogenic microorganisms.
研究领域:
生物化学
·
医学影像
·
肿瘤学
✓ 已验证
DOI
PubMed
高影响因子
MICROPOROUS AND MESOPOROUS MATERIALS
·
2020
·
IF 4.551
Yu Zhu,Nan Song,Li Chen,Zhigang Xie
In this work, we decorated the surface hydroxyl of mesoporous silica nanoparticles (MSNs-OH) by using iodine BODIPY containing disulfide bond and carboxyl group (I 2 BDP–SS–COOH) for photodynamic therapy. To improve the water solubility, the MSNs were further PEGylated by PEG–SS–COOH to prepare MSNs-I 2 BDP-PEG. The particle size and stability of MSNs-I 2 BDP-PEG were characterized by the transmission electron microscopy (TEM) and dynamic light scattering (DLS). The confocal laser imaging and cells cytotoxicity experiments indicated that MSNs-I 2 BDP-PEG could be endocytosed well, and the intracellular higher concentrations of glutathione in tumor cells could stimulate the cleavage of disulfide bonds to release BODIPY for photodynamic therapy. This work highlights the great potential of post-modificating silica nanoparticles as multifunctional materials in biomedical fields.
研究领域:
纳米医学
·
生物材料学
·
肿瘤治疗学
✓ 已验证
DOI
高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2024
·
IF 4.3
Wen-Jie Mao,Tian-Tian Wang,Lin Chen,Lei Zhang,Shan Li
Tyramine signaling amplification (TSA) technology is generally applied in immunofluorescence, enzyme-linked immunoassays, in situ hybridization techniques, etc. Successful amplification of fluoresence signals cannot be achieved without excellent fluorescent dyes. BODIPY fluorophore is an ideal probe for cell fluorescence imaging, but pristine BODIPY cannot be direct used in the TSA system. In the paper, the new red-shifted tyramide-conjugated BODIPY ( BDP-B/C/D ) was synthesized via the Knoevenagel condensation reaction, which based on the tyramide-conjugated BODIPY (BDP-A). The synthesized dyes were combined with tyramine to obtain which could be used as a fluorescent substrate for enzymatic reaction of TSA. By using the selected substrate ( BDP-C ) in TSA, we found it to be more sensitive than the commercial dye 594 styramide for the detection of low-abundance antigen proteins.
研究领域:
生物化学
·
细胞生物学
·
医学影像学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
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