- N-Alkylation of 2-methoxy-10H-phenothiazine revisited. A facile entry to diversely N-substituted phenothiazine-coumarin hybrid dyes
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N-Alkylation of 2-methoxy-10H-phenothiazine, a valuable building block for the synthesis of bioactive compounds and reaction-based fluorescent probes, has been revisited aimed at introducing a substituent easily convertible into cationic or zwitterionic side chains. We focused our attention on the 3-dimethylaminopropyl group since its derivatization through reactions with various alkyl halides or sultones is a well-established and effective way to enhance polarity of diverse hydrophobic molecular scaffolds. This two-step functionalization approach was applied to the synthesis of novel phenothiazine-coumarin hybrid dyes whose spectral features, especially their NIR-I emission, have been determined in aqueous media with the ultimate goal of identifying novel fluorescent markers for bioanalytical applications, including fluorogenic detection of reactive oxygen species (ROS) through selective S-oxidation reaction of phenothiazine scaffold.
- Quesneau, Valentin,Renault, Kévin,Laly, Myriam,Jenni, Sébastien,Ponsot, Flavien,Romieu, Anthony
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supporting information
(2020/11/16)
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- Colorimetric recognition of the length of α,ω-diamines in water
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Two types of host molecules based on phenolphthalein and two crown ethers have been constructed. These hosts made it possible to recognize the length of α,ω-diamines and transformed the binding events into detectable changes in color in an aqueous buffer
- Tsubaki, Kazunori,Tanima, Daisuke,Sasamori, Takahiro,Tokitoh, Norihiro,Kawabata, Takeo
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p. 2135 - 2138
(2008/02/04)
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- Nanostructured oligo(p-phenylene vinylene)/silicate hybrid films: One-step fabrication and energy transfer studies
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Novel hybrid materials containing silicate and charged oligo(p-phenylene vinylene) (OPV) amphiphiles were fabricated in one step by spin casting using evaporation-induced self assembly. The conjugated segments were substituted with trimethylammonium bromide groups at both termini, and tetraethyl orthosilicate served as the silicate precursor. X-ray diffraction scans of the hybrid films revealed Bragg diffraction peaks with d-spacings of 2.76 and 1.37 nm, indicating the presence of order in the hybrid structure. Optical properties of the hybrid films were characterized by UV-vis absorption and fluorescence spectra, and molecular orientation was characterized by IR spectroscopy. A rhodamine B derivative containing a triethoxysilane group was covalently incorporated into the silicate network of the films during the sol-gel reaction. Relative to disordered polymer films with identical organic composition, the ordered hybrid films revealed significantly enhanced emission from rhodamine B and also fluorescence quenching from OPV segments. These results indicate that the ordered and nanostructured environment leads to highly efficient energy transfer among organic components in these hybrid films.
- Tajima, Keisuke,Li, Liang-Shi,Stupp, Samuel I.
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p. 5488 - 5495
(2007/10/03)
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- OLIGO(P-PHENYLENE VINYLENE) AMPHIPHILES AND METHODS FOR SELF-ASSEMBLY
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Amphiphilic oligo(p-phenylene vinylene) compounds and methods of use en route to self-assembled composites and device fabrication.
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Page/Page column 19
(2008/06/13)
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- Molecular recognition abilities of a new class of water-soluble cyclophanes capable of encompassing a neutral cavity
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We developed a new class of water-soluble cyclophanes, pyrenophanes, capable of encompassing a neutral cavity, in which the hydrophobic area is constructed by aligning two flat polynuclear aromatic rings parallel at an appropriate space that could interpo
- Inouye, Masahiko,Fujimoto, Kazuhisa,Furusyo, Masaru,Nakazumi, Hiroyuki
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p. 1452 - 1458
(2007/10/03)
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