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Nicolas Leclerc, Ibrahim Bulut, Quentin Huaulmé, Antoine Mirloup, Patricia Chávez, Sadiara Fall, Anne Hébraud, Stéphane Méry, Benoit Heinrich, Thomas Heiser, Patrick Lévêque
Boron dipyrromethene (Bodipy) are known to be efficient photon harvesting chromophores. However, their study as active materials in bulk heterojunction (BHJ) solar cells is still scarce. In this paper, we developed new synthetic ways to design original Bodipy-based dumbbell-shape molecules, including a first 2,3,5,6-tetravinyl aromatic Bodipy molecule. We demonstrated that high fill factors can be obtained in BHJ solar cells when blended with a fullerene derivative, leading to a new Bodipy-based record power conversion efficiency of 5...
March 21, 2017: ChemSusChem
Shumin Yang, Ting Li, Aipin Zhang, Rufei Gao, Chuan Peng, Lulu Liu, Qingfeng Cheng, Mei Mei, Ying Song, Xiaojiao Xiang, Chaodong Wu, Xiaoqiu Xiao, Qifu Li
Context: Accumulating evidence suggests that bisphenol A (BPA) exposure is associated with nonalcoholic fatty liver disease. Disruption of autophagy causes lipid accumulation in hepatocytes. Whether and how BPA regulates autophagy remains to be explored. Objective: We investigated the effect of BPA on autophagy in hepatocytes and examined the influence of BPA-regulated autophagy on hepatic lipid accumulation. Design: Male CD1 mice were treated with BPA for eight weeks, followed by histological and biochemical evaluation of liver lipids and autophagy...
February 21, 2017: Endocrinology
Dumitru Sirbu, Andrew C Benniston, Anthony Harriman
Tin(IV) catalysis allows isolation of a boron dipyrromethene derivative bearing a solitary strap around the boron center. The conditions favor internal cyclization without contamination by side products and provide high yields of product in good purity. A phenolate-based strap imposes chirality and causes geometrical distortion of the dipyrrin. Relatively strong fluorescence is observed for single crystals, evaporated films, and adsorbed layers. Single-crystal absorption and emission spectra resemble those observed from solution with contributions from a dimer...
March 20, 2017: Organic Letters
Lijing Yang, Brett Drew, Ravi Shekar Yalagala, Rameez Chaviwala, Razvan Simionescu, Alan J Lough, Hongbin Yan
In the title compound (3-amino-4,4-diphenyl-BODIPY), C28H32BN3, the central six-membered ring has a flattened sofa conformation, with one of the N atoms deviating by 0.142 (4) Å from the mean plane of the other five atoms, which have an r.m.s. deviation of 0.015 Å. The dihedral angle between the two essentially planar outer five-membered rings is 8.0 (2)°. In the crystal, mol-ecules are linked via weak N-H⋯π inter-actions, forming chains along [010]. The com-pound displays solvent-dependent behaviours in both NMR and fluorescence spectroscopy...
March 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
Hui He, Shuangshuang Ji, Yang He, Aijun Zhu, Yelin Zou, Yibin Deng, Hengte Ke, Hong Yang, Youliang Zhao, Zhengqing Guo, Huabing Chen
Photoconversion tunability of fluorophore dye is of great interest in cancer nanomedicine such as fluorescence imaging, photodynamic therapy (PDT), and photothermal therapy (PTT). Herein, this paper reports wavelength-dependent photoconversional polymeric vesicles of boron dipyrromethene (Bodipy) fluorophore for either PDT under 660 nm irradiation or PTT under 785 nm irradiation. After being assembled within polymeric vesicles at a high drug loading, Bodipy molecules aggregate in the conformations of both J-type and H-type, thereby causing red-shifted absorption into near-infrared region, ultralow radiative transition, and ideal resistance to photobleaching...
March 15, 2017: Advanced Materials
A Vanessa Saura, M Isabel Burguete, Francisco Galindo, Santiago V Luis
Three bichromophoric compounds containing anthracene and bodipy moieties connected by different spacers have been synthesized and fully characterized. The set of spacers comprises a variety of bridges (short and flexible 1,2-diaminoethane in compound 1a, long and flexible 1,8-diaminooctane in compound 1b and short and rigid piperazine in compound 1c). The new compounds show interchromophoric communication via Electronic Energy Transfer (EET). When anthracene is excited, the energy is efficiently transferred to the bodipy moiety...
March 15, 2017: Organic & Biomolecular Chemistry
Prusothman Yoganantharjah, Avinesh R Byreddy, Daniel Fraher, Munish Puri, Yann Gibert
The zebrafish is a useful vertebrate model to study lipid metabolism. Oil Red-O (ORO) staining of zebrafish embryos, though sufficient for visualizing the localization of triglycerides, was previously inadequate to quantify neutral lipid abundance. For metabolic studies, it is crucial to be able to quantify lipids during embryogenesis. Currently no cost effective, rapid and reliable method exists to quantify the deposition of neutral lipids and triglycerides. Thin layer chromatography (TLC), gas chromatography and mass spectrometry can be used to accurately measure lipid levels, but are time consuming and costly in their use...
2017: International Journal of Developmental Biology
Christian Paul Ortmeyer, Günter Haufe, Katrin Schwegmann, Sven Hermann, Michael Schäfers, Frederik Börgel, Bernhard Wünsch, Stefan Wagner, Verena Hugenberg
BODIPYs (boron dipyrromethenes) are fluorescent dyes which show high stability and quantum yields. They feature the possibility of selective (18)F-fluorination at the boron-core. Attached to a bioactive molecule and labeled with [(18)F]fluorine, the resulting compounds are promising tracers for multimodal imaging in vivo and can be used for PET and fluorescence imaging. A BODIPY containing a phenyl and a hydroxy substituent on boron was synthesized and characterized. Fluorinated and hydroxy substituted dyes were coupled to an isatin-based caspase inhibitor via cycloaddition and the resulting compounds were evaluated in vitro in caspase inhibition assays...
February 16, 2017: Bioorganic & Medicinal Chemistry
Youngsam Kim, Taehong Jun, Sandip V Mulay, Sudesh T Manjare, Jinseong Kwak, Yunho Lee, David G Churchill
A new BODIPY system displaying an intramolecular π-π-interaction was synthesized and studied. When the selenium center was oxidized, the substituted phenyl group undergoes π-π stacking with one side of the BODIPY core. The oxidized form showed, not only a down-field shift in the NMR peak, but also splitting due to geometrical changes that arise when going from Cs to C1. The compound was characterized by X-ray diffraction; DFT methods helped elucidate the influence of the unexpected π-π stack and its connection to the photophysical properties imparted by the Se oxidation...
March 9, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
Martin Strobl, Anna Walcher, Torsten Mayr, Ingo Klimant, Sergey M Borisov
Highly sensitive ammonia sensors for environmental monitoring are presented. The sensing materials are based on fluorescent BF2-chelated tetraarylazadipyrromethene dyes (aza-BODIPYs) dyes physically entrapped in polyurethane hydrogels and dispersed in silicone rubber. This layer is covered by a hydrophobic porous Teflon membrane used as an additional proton barrier and light scattering layer. The dual-lifetime referenced (DLR) sensors make use of near-infrared (NIR)-emitting Egyptian blue as a reference material and in combination with optical fibers are read-out via a compact phase-fluorometer...
March 7, 2017: Analytical Chemistry
Fiona A Black, Charlotte A Clark, Gareth H Summers, Ian P Clark, Michael Towrie, Thomas Penfold, Michael W George, Elizabeth A Gibson
Understanding what influences the formation and lifetime of charge-separated states is key to developing photoelectrochemical devices. This paper describes the use of time-resolved infrared absorption spectroscopy (TRIR) to determine the structure and lifetime of the intermediates formed on photoexcitation of two organic donor-π-acceptor dyes adsorbed to the surface of NiO. The donor and π-linker of both dyes is triphenylamine and thiophene but the acceptors differ, maleonitrile (1) and bodipy (2). Despite their structural similarities, dye 1 outperforms 2 significantly in devices...
March 6, 2017: Physical Chemistry Chemical Physics: PCCP
Lies Jordaens, Veerle Van Hoeck, Veronica Maillo, Alfonso Gutierrez-Adan, Waleed Fawzy A Marei, Bruno Vlaeminck, Sofie Thys, Roger G S Sturmey, Peter Bols, Jo Leroy
We hypothesized that elevated non-esterified fatty acids (NEFA) modify in vitro bovine oviduct epithelial cell (BOEC) metabolism and barrier function. Hereto, BOECs were studied in a polarized system with 24h-treatments at day 9: 1) CONTROL (0µM NEFA + 0%EtOH), 2) SOLVENT CONTROL (0µM NEFA + 0.45%EtOH), 3) BASAL NEFA (720µM NEFA + 0.45%EtOH in the basal compartment), 4) APICAL NEFA (720µM NEFA + 0.45%EtOH in the apical compartment). FITC-albumin was used for monolayer permeability assessment, and related to Transepithelial Electric Resistance (TER)...
March 3, 2017: Reproduction: the Official Journal of the Society for the Study of Fertility
Hong-Cheng Xia, Xiang-Hong Xu, Qin-Hua Song
As a highly toxic and widely used chemical, phosgene has become a serious threat to humankind and public security because of its potential use by terrorists and unexpected release during industrial accidents. For this reason, it is an urgent need to develop facile, fast, and selective detection methods of phosgene. In this Article, we have constructed a highly selective fluorescent sensor o-Pab for phosgene with a BODIPY unit as a fluorophore and o-phenylenediamine as a reactive site. The sensor o-Pab exhibits rapid response (∼15 s) in both colorimetric and turn-on fluorescence modes, high selectivity for phosgene over nerve agent mimics and various acyl chlorides and a low detection limit (2...
March 14, 2017: Analytical Chemistry
Patrycja Stachelek, Abdulrahman A Alsimaree, Rua B Alnoman, Anthony Harriman, Julian G Knight
A small series of boron dipyrromethene (BODIPY) dyes has been synthesized whereby the boron atom is constrained in a five-membered ring formed from either o-dihydroxypyridine or o-aminophenol. In the latter case, the amino group has been converted into the corresponding amide derivative so as to curtail the possibility for light-induced charge transfer from strap to BODIPY. These compounds are weakly emissive in fluid solution but cleavage of the strap, by treatment with a photoacid generator, restores strong fluorescence...
March 8, 2017: Journal of Physical Chemistry. A
Iwao Nakamura, Eiji Ichimura, Rika Goda, Hitomi Hayashi, Hiroko Mashiba, Daichi Nagai, Hirofumi Yokoyama, Takeshi Onda, Akira Masuda
In our previous rodent studies, the paclitaxel (PTX)-incorporating polymeric micellar nanoparticle formulation NK105 had showed significantly stronger antitumor effects and reduced peripheral neurotoxicity than PTX dissolved in Cremophor(®) EL and ethanol (PTX/CRE). Thus, to elucidate the mechanisms underlying reduced peripheral neurotoxicity due to NK105, we performed pharmacokinetic analyses of NK105 and PTX/CRE in rats. Among neural tissues, the highest PTX concentrations were found in the dorsal root ganglion (DRG)...
2017: International Journal of Nanomedicine
Nagaiyan Sekar, Ramaiah D, Yogesh Gawale, Adarsh N, Joseph J, M Pramanik, S K Kalva
Four novel N-ethylcarbazole linked aza-BODIPY dyes (8a-b and 9a-b) were synthesized and characterized. The presence of N-ethylcarbazole moiety shifts their absorption and fluorescence spectra to the near-infrared region, ca. 650-730 nm, of electromagnetic spectra. These dyes possess strong molar absorptivity in the range of 3-4 x 104 M-1cm-1 with low fluorescence quantum yields. The triplet excited state as well as singlet oxygen generation of these dyes were enhanced upon iodination at the core position. The core iodinated dyes 9a-b showed excellent triplet quantum yield of ca...
February 22, 2017: Chemistry: a European Journal
M Hassan Pervaiz, Sridevi Durga, Abed Janoudi, Kevin Berger, George S Abela
BACKGROUND: PET/CTA was used to evaluate the effect of cholesterol crystal emboli (CCE) on muscle injury. Cholesterol crystals (CCs) released during plaque rupture travel downstream and lodge in muscle triggering inflammation and tissue injury. METHODS: Thigh muscles in three groups of rabbits (n = 22) were studied after intra-arterial injection of CCs, Group I (n = 10); polystyrene microspheres, Group II (n = 5); or normal saline, Group III (n = 7). After 48 hours, muscle inflammation and injury were measured by fluorodeoxy-glucose uptake using PET/CTA, serum tissue factor (TF), and creatinine phosphokinase (CPK)...
February 21, 2017: Journal of Nuclear Cardiology: Official Publication of the American Society of Nuclear Cardiology
Mina Raeisolsadati Oskouei, Albert M Brouwer
Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis.
February 21, 2017: Journal of Fluorescence
Bingbing Cheng, Venugopal Bandi, Shuai Yu, Francis D'Souza, Kytai T Nguyen, Yi Hong, Liping Tang, Baohong Yuan
Highly environment-sensitive fluorophores have been desired for many biomedical applications. Because of the noninvasive operation, high sensitivity, and high specificity to the microenvironment change, they can be used as excellent probes for fluorescence sensing/imaging, cell tracking/imaging, molecular imaging for cancer, and so on (i.e., polarity, viscosity, temperature, or pH measurement). In this work, investigations of the switching mechanism of a recently reported near-infrared environment-sensitive fluorophore, ADP(CA)₂, were conducted...
February 11, 2017: International Journal of Molecular Sciences
Deyan Gong, Xiangtao Zhu, Yuejun Tian, Shi-Chong Han, Min Deng, Anam Iqbal, Weisheng Liu, Wenwu Qin, Huichen Guo
Herein a phenylselenium-substituted BODIPY (1) fluorescent turn-off sensor was developed for the purpose to achieve excellent selectivity and sensitivity for H2S detection based on the substitution reaction of the phenylselenide group at the 3-position with H2S. The excess addition of hydrogen sulfide promoted further substitution of the phenylselenide group at the 5-position of the probe and was accompanied by a further decrease in fluorescence emission intensity. Sensor 1 demonstrated remarkable performance with 49-fold red color fluorescence intensity decrease at longer excitation wavelength, a low detection limit (0...
February 7, 2017: Analytical Chemistry
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