1308671-66-0Relevant articles and documents
Red/NIR neutral BODIPY-based fluorescent probes for lighting up mitochondria
Yang, Jian,Zhang, Ran,Zhao, Yue,Tian, Jiangwei,Wang, Shifa,Gros, Claude P.,Xu, Haijun
, (2021)
Two mitochondrial-targeted fluorescent probes, 2 and 3, based on a BODIPY scaffold and one or two piperidinyl groups were easily synthesized by Knoevenagel condensation. The biological imaging applications of the two probes 2 and 3 in live HepG2 cells reveal that these two probes display excellent mitochondrial imaging ability. Thus, these probes appear as promising tools for visualization of mitochondrial within live cells.
Catalyst Halogenation Enables Rapid and Efficient Polymerizations with Visible to Far-Red Light
Stafford, Alex,Ahn, Dowon,Raulerson, Emily K.,Chung, Kun-You,Sun, Kaihong,Cadena, Danielle M.,Forrister, Elena M.,Yost, Shane R.,Roberts, Sean T.,Page, Zachariah A.
, p. 14733 - 14742 (2020)
The driving of rapid polymerizations with visible to near-infrared light will enable nascent technologies in the emerging fields of bio- and composite-printing. However, current photopolymerization strategies are limited by long reaction times, high light
Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells
Yang, Jian,Devillers, Charles H.,Fleurat-Lessard, Paul,Jiang, Hao,Wang, Shifa,Gros, Claude P.,Gupta, Gaurav,Sharma, Ganesh D.,Xu, Haijun
, p. 5606 - 5617 (2020)
Two BODIPY derivatives with one (B2) and two (B3) carbazole moieties were synthesized and applied as electron-donor materials in organic photovoltaic cells (OPV). Their optical and electrochemical properties were systematically investigated. These BODIPY dyes exhibit excellent solubility in organic solvents and present high molar extinction coefficients (1.37-1.48 × 105M?1cm?1) in solutions with absorption maxima at 586 nm for mono-styryl groups and at 672 nm for di-styryl groups. The introduction of the styryl moieties results in a large bathochromic shift and a significant decrease in the HOMO-LUMO energy-gaps. The BODIPY dyes show relatively low HOMO energies ranging from ?4.99 to ?5.16 eV as determined from cyclic voltammetry measurements. Cyclic voltammetry measurements and theoretical calculations demonstrate that the frontier molecular orbital levels of these compounds match with those of PC71BM as the acceptor, supporting their application as donor materials in solution-processed small molecule bulk heterojunction (BHJ) organic solar cells. After the optimization of the active layer,B2:PC71BM andB3:PC71BM based organic solar cells showed an overall power conversion efficiency of 6.41% and 7.47%, respectively. The higher PCE of theB3-based OSC is ascribed to the more balanced charge transport and exciton dissociation, better crystallinity and molecular packing.
Substituent Effects in BODIPY in Live Cell Imaging
Mulay, Sandip V.,Yudhistira, Tesla,Choi, Minsuk,Kim, Youngsam,Kim, Jinjoo,Jang, Yoon Jeong,Jon, Sangyong,Churchill, David G.
, p. 3598 - 3605 (2016)
Small-molecule organoselenium-based fluorescent probes possess great capacity in understanding biological processes through the detection of various analytes such as reactive oxygen/nitrogen species (ROS/RNS), biothiols (cysteine, homocysteine and glutathione), lipid droplets, etc. Herein, we present how substituents on the BODIPY system play a significant part in the detection of biologically important analytes for in vitro conditions and live cell imaging studies. The fluorescence of the probe was quenched by 2-chloro and 6-phenyl selenium groups; the probe shows high selectivity with NaOCl among other ROS/RNS, and gives a turn-on response. The maximum fluorescence intensity is attained within ≈1–2 min with a low detection limit (19.6 nm), and shows a ≈110-fold fluorescence enhancement compared to signals generated for other ROS/RNS. Surprisingly, in live cell experiments, the probe specifically located and accumulated in lipid droplets, and showed a fluorescence turn-on response. We believe this turn-on response occurred because of aggregation-induced emission (AIE), which surprisingly occurred only by introducing one lipophilic mesityl group at the meso position of the BODIPY.
Tuning the photo-physical properties of BODIPY dyes: Effects of 1, 3, 5, 7- substitution on their optical and electrochemical behaviours
Tao, Jiayu,Sun, Dan,Sun, Lei,Li, Zhengzheng,Fu, Bo,Liu, Jian,Zhang, Lei,Wang, Shifa,Fang, Yuanyuan,Xu, Haijun
, p. 166 - 174 (2019)
Five BODIPY derivatives containing different number of styryl units were designed and synthesized based on the Knoevenagel reactions. All compounds were characterized by NMR and HRMS. The single crystal structures of compounds 1 and 3–5 were confirmed by
Synthesis and investigation of BODIPYs with restricted meso -8-aryl rotation
Zhang, Guanyu,Wang, Maodie,Ndung'u, Caroline,Bobadova-Parvanova, Petia,Fronczek, Frank R.,Smith, Kevin M.,Vicente, M. Gra?a H.
, p. 869 - 877 (2020)
Three BODIPYs bearing 1,3,5,7-tetramethyl substituents and a meso-8-aryl group were synthesized and investigated, both experimentally and computationally. The presence of the 1,7-methyl groups and of ortho-substituents on the meso-8-aryl ring prevent free
BODIPY Dyes Bearing Multibranched Fluorinated Chains: Synthesis, Structural, and Spectroscopic Studies
Martinez Espinoza, Maria I.,Sori, Lorenzo,Pizzi, Andrea,Terraneo, Giancarlo,Moggio, Ivana,Arias, Eduardo,Pozzi, Gianluca,Orlandi, Simonetta,Dichiarante, Valentina,Metrangolo, Pierangelo,Cavazzini, Marco,Baldelli Bombelli, Francesca
, p. 9078 - 9087 (2019)
A small series of boron-dipyrromethene (BODIPY) dyes, characterized by the presence of multibranched fluorinated residues, were designed and synthesized. The dyes differ in both the position (para-perfluoroalkoxy-substituted phenyl ring or boron functiona
BODIPY-based fluorescent probe for selective detection of HSA in urine
Cheng, Tanyu,Duan, Liping,Han, Xiumin,Peng, Cheng,Shen, Guohua,Xu, Hui
, (2021/11/01)
Quantitative recognition of human serum albumin (HSA) is of great importance in the fields of biology and biomedicine. In biological fluids, HSA has been used as an important biomarker for disease early diagnosis. For example, microalbuminuria has been re
Highly efficient BODIPY-doped upconversion nanoparticles for deep-red luminescence bioimagingin vivo
Jia, Ti,Wang, Qiuhong,Xu, Ming,Yuan, Wei,Feng, Wei,Li, Fuyou
supporting information, p. 1518 - 1521 (2021/02/21)
We demonstrate a 3,5-di(p-oxethyl)styryl conjugated BODIPY showing deep-red upconversion luminescence with a high efficiency of 16.6%. Furthermore, water-soluble BODIPY-doped upconversion nanoparticles with efficiency up to 6.9% under low excitation power
Near-Infrared BODIPY-Acridine Dyads Acting as Heavy-Atom-Free Dual-Functioning Photosensitizers
Deckers, Jasper,Cardeynaels, Tom,Penxten, Huguette,Ethirajan, Anitha,Ameloot, Marcel,Kruk, Mikalai,Champagne, Beno?t,Maes, Wouter
, p. 15212 - 15225 (2020/10/19)
Boron dipyrromethene (BODIPY) dyes represent a particular class within the broad array of potential photosensitizers. Their highly fluorescent nature opens the door for theragnostic applications, combining imaging and therapy using a single, easily synthesized chromophore. However, near-infrared absorption is strongly desired for photodynamic therapy to enhance tissue penetration. Furthermore, singlet oxygen should preferentially be generated without the incorporation of heavy atoms, as these often require additional synthetic efforts and/or afford dark cytotoxicity. Solutions for both problems are known, but have never been successfully combined in one simple BODIPY material. Here, we present a series of compact BODIPY-acridine dyads, active in the phototherapeutic window and showing balanced brightness and phototoxic power. Although the donor–acceptor design was envisioned to introduce a charge transfer state to assist in intersystem crossing, quantum-chemical calculations refute this. Further photophysical investigations suggest the presence of exciplex states and their involvement in singlet oxygen formation.
