15770-21-5Relevant articles and documents
Pairing of α-Fused BODIPY: Towards Panchromatic n-Type Semiconducting Materials
Huaulmé, Quentin,Fall, Sadiara,Lévêque, Patrick,Ulrich, Gilles,Leclerc, Nicolas
, p. 6613 - 6620 (2019)
A chemical strategy to efficiently perform the dimerization of α-fused boron-dipyrromethene (BODIPY) is reported. The straightforward synthesis of one of these dimers is described and its properties have been investigated through UV/Vis spectroscopy, cyclic voltammetry, differential scanning calorimetry, and charge-carrier mobility measurements by using organic field-effect transistors and space–charge-limited current diodes. The results allow a chemical strategy to decrease the tendency of α-fused BODIPY to crystallize, to increase its light-harvesting properties, and to promote isotropic charge carriers transport. Moreover, the disclosed approach is also a way to maintain the deep LUMO level of α-fused BODIPY; thus making this class of materials highly desirable for optoelectronic applications.
Aggregation-Induced Singlet Oxygen Generation: Functional Fluorophore and Anthrylphenylene Dyad Self-Assemblies
Kim, Sooyeon,Zhou, Yang,Tohnai, Norimitsu,Nakatsuji, Hirotaka,Matsusaki, Michiya,Fujitsuka, Mamoru,Miyata, Mikiji,Majima, Tetsuro
, p. 636 - 645 (2018)
The assembly of monomeric building blocks can manifest the display of new properties, including optical, mechanical, and electrochemical functionalities. In this study, we sought to develop a functional fluorophore self-assembly that can generate reactive oxygen species only when aggregated. With an anthrylphenylene (AP) group, negatively charged and neutral fluorescein units form non-fluorescent H-aggregates in aqueous solution because of the weak intermolecular interaction between the anthracene and fluorescein moieties. In stark contrast, a boron dipyrromethene (BODIPY) and AP dyad produces two-color-emissive aggregates through the formation of an intermolecular charge-transfer (CT) complex between the electron-rich anthracene and electron-deficient BODIPY moieties. Furthermore, to our surprise, the BODIPY and AP dyad aggregates generate singlet oxygen (1O2) and photocytotoxicity upon excitation, indicating that the BODIPY–anthracene CT state favors an intersystem crossing process. Based on X-ray crystallographic analysis, the lattice-like molecular packing between the BODIPY and AP moieties was determined to bring about the unprecedented aggregation-induced 1O2 generation (AISG).
Synthesis and photodynamic activity of novel non-symmetrical diaryl porphyrins against cancer cell lines
Caruso, Enrico,Cerbara, Monica,Malacarne, Miryam Chiara,Marras, Emanuela,Monti, Elena,Gariboldi, Marzia Bruna
, p. 39 - 50 (2019)
Photodynamic therapy (PDT)of cancer uses photosensitizers (PS), a light source and oxygen to generate high levels of reactive oxygen species (ROS), that exert a cytotoxic action on tumor cells. Recently, it has been shown that mixed non-symmetrical diaryl porphyrins, with two different pendants, are more photodynamically active than symmetrical diaryl porphyrins. In the present study, we investigate the in vitro photodynamic effects of four novel non-symmetrical diaryl porphyrins, two of which bear one pentafluoro-phenyl and one bromo-alkyl (apolar)pendant, whereas the two others bear one pentafluoro-phenyl and one cationic pyridine pendant. The four compounds were tested in a small panel of human cancer cell lines, and their photodynamic activities were compared with that of m-THPC (Foscan), currently the most successful PS approved for clinical use in cancer PDT. The results of the cytotoxicity studies indicate that the two molecules bearing the cationic pendant are more potent in vitro than those with the apolar pendant, and that they are as potent as Foscan. To gain further insights into the mechanism of PS-induced phototoxicity, induction of apoptotic, autophagic and necrotic cell death, and generation of reactive oxygen species (ROS)were evaluated in cancer cells following exposure to the PSs and irradiation. The effect of the PSs on the migratory activity of the cells was also assessed. The data obtained from this work support a greater potency of diaryl porphyrins with a positive charge in inducing cell death, as compared to those with the bromo-alkyl pendant; most importantly, some of these novel compounds exhibit features that might make them superior to the clinically approved PS Foscan.
A BODIPY-based two-photon fluorescent probe validates tyrosinase activity in live cells
Naidu Bobba, Kondapa,Won, Miae,Shim, Inseob,Velusamy, Nithya,Yang, Zhigang,Qu, Junle,Kim, Jong Seung,Bhuniya, Sankarprasad
, p. 11213 - 11216 (2017)
Herein, we report rational design, synthesis, and application of a two-photon fluorescent probe (Tyro-1) for tracking intracellular tyrosinase activity. The chemoselective detection of tyrosinase is precluded from interference of other competitive omnipresent oxidizing entities in cellular milieu. The probe showed 12.5-fold fluorescence enhancement at λem = 450 nm in the presence of tyrosinase. The nontoxic probe Tyro-1 provides information about H2O2-mediated upregulation of tyrosinase through cellular imaging. Its two-photon imaging ability makes it a noninvasive tool for validating the expression of tyrosinase in the live cells.
COMPOUND, COLOR CONVERSION FILM COMPRISING SAME, BACK-LIGHT UNIT, AND DISPLAY DEVICE
-
Paragraph 0161-0163; 0172, (2021/05/21)
The present specification relates to a compound represented by Chemical Formula 1, and a color conversion film, a backlight unit and a display apparatus including the same.
Fluorescent sensor for rapidly and sensitively detecting phosgene as well as preparation method and application of fluorescent sensor
-
Paragraph 0033-0034, (2021/12/07)
The invention discloses a compound BODIPY-AP. The compound BODIPY-AP takes BODIPY as a fluorescent group and 2-aminophenol as a recognition group. The compound BODIPY-AP can be used as a fluorescent sensor for rapidly and highly sensitively detecting phosgene. The sensor shows specific chromogenic reaction and fluorescence enhanced response to phosgene, so the concentration of phosgene can be detected through color-fluorescence dual visual signal changes, and the sensor has good selectivity to phosgene. The fluorescent sensor disclosed by the invention has the advantages of ultrahigh sensitivity, transient responsiveness, ultralow detection limit and high signal-to-noise ratio, and is suitable for rapidly and sensitively detecting phosgene; and moreover, the manufacturing process of the sensor is simple, cost is low, and the practical popularization and application of the sensor are very easy. The fluorescent sensor can be made into portable detection test paper for real-time monitoring of phosgene, can be used for rapid detection of phosgene leakage, especially can detect phosgene content in real time in an industrial production process or in other gas environments, and has great application prospects for safety production in the chemical industry.
Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors
Alemán, José,Asenjo-Pascual, Juan,Cordani, Marco,Díaz-Tendero, Sergio,Fraile, Alberto,Martín-Somer, Ana,Milán Rois, Paula,Rigotti, Thomas,Somoza, álvaro
supporting information, (2020/02/20)
In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron-withdrawing group for activation of double bonds in asymmetric copper-catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron-withdrawing group. Experimental, theoretical studies and comparison with other common electron-withdrawing groups in asymmetric copper-catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines. (Figure presented.).
Triple molten porphyrin dimer covalent functionalized single-walled carbon nanotube nonlinear nano hybrid material and preparation method thereof
-
Paragraph 0058; 0061, (2020/12/30)
The invention relates to a triple molten porphyrin dimer covalent functionalized single-walled carbon nanotube non-linear nano hybrid material and a preparation method thereof. The non-linear nano hybrid material is formed by connecting a triple molten porphyrin dimer TFP to the surface of SWCNT through covalent bonds. Compared with the prior art, the organic-inorganic covalent functionalized nanofunctional material is prepared by connecting TFP to the surface of SWCNT through covalent bonds and the azo salt free radical addition reaction instead of simply and physically mixing the two different optical functional materials, and compared with a traditional material, the prepared material not only has enhanced nonlinear optical properties in the nanosecond visible light field, but also canconvert saturated absorption of a traditional material into anti-saturated absorption in the femtosecond near-infrared field, and has a very wide application prospect.
Modifiable hyperconjugation triple molten porphyrin dimer strong two-photon absorption material and preparation thereof
-
Paragraph 0045; 0048, (2020/11/09)
The invention relates to a modifiable hyperconjugation triple molten porphyrin dimer strong two-photon absorption material and preparation thereof. In two edge meso positions of a porphyrin dimer, oneof the two edge meso positions of the porphyrin dimer is provided with anilino, and the other of the two edge meso positions of the porphyrin dimer is provided with acetanilino. Compared with the prior art, the preparation method comprises the following steps: selectively modifying aniline groups on single porphyrin with vacancy at double meso sites in a unilateral manner, performing protection in advance, further separating out a symmetrical molten porphyrin dimer with two acetanilide groups through low-temperature oxidation and low-temperature extraction modes, and finally preparing a target compound with one anilino group and one acetanilino group through a unilateral deprotection reaction, namely the asymmetric triple molten porphyrin dimer TFP. The material not only has the strong TPA characteristic of the triple molten porphyrin dimer, but also is very easy to modify, provides possibility for preparing diversified nonlinear and other functional materials with a wider applicationrange, and has a good application prospect.
COMPOUND AND COLOR CONVERSION FILM COMPRISING THE SAME
-
Paragraph 0106-0107, (2020/03/28)
The present specification relates to a compound, and a color conversion film, a backlight unit, and a display device, including the same.
