28320-32-3Relevant articles and documents
Tricolor Luminescence Switching by Thermal and Mechanical Stimuli in the Crystal Polymorphs of Pyridyl-substituted Fluorene
Guan, Jianping,Xu, Fan,Tian, Chang,Pu, Liang,Yuan, Mao-Sen,Wang, Jinyi
, p. 216 - 222 (2019)
Stimuli-responsive organic luminescence-switching materials have attracted much attention for a decade. Most of the reported examples display a reversible two-color luminescence switching, and multicolor-switching materials remain extremely rare. Herein, we report a simple organic molecule, 4,4′-(9,9-dimethyl-9H-fluorene-2,7-diyl)dipyridine (MFDP), which exhibits three different crystal polymorphs (V-MFDP, B-MFDP and G-MFDP) with different luminescent colors. Furthermore, the three crystal polymorphs show a reversible tricolor fluorescent switching from violet to blue and to green upon physical stimuli. The single-crystal structures of the three polymorphs were obtained, and the results indicate that the stimuli-responsive properties of the three polymorphs come from the different stacking modes induced by intermolecular interactions. The competition between weak π–π stacking and weak hydrogen bonding is the main reason for the the phase transformations among the three crystal polymorphs.
Lanthanide–organic framework based on a 4,4-(9,9-dimethyl-9H-fluorene-2,7-diyl) dibenzoic acid: Synthesis, structure and fluorescent sensing for a variety of cations and anions simultaneously
Li, Bing,Zhou, Jun,Bai, Fengying,Xing, Yongheng
, (2020)
Based on the structural diversity and the superior luminescence properties of 4,4-(9,9-dimethyl-9H-fluorene-2,7-diyl) dibenzoic acid (H2DLDA), a series of new lanthanide coordination compounds [Ln(DLDA)(DMF)(H2O)(COO)]n (Sm (1), Eu (2), Ce (3), Nd (4), Gd (5)) were successfully prepared by the reaction of H2DLDA, which is a new type ligand synthesized by structural modification of fluorene, with rare earth metal ion. They were characterized by elemental analysis, IR, TG, PXRD, UV–vis, etc. Analysis results show that the coordination compounds are isomorphic. In particular, the structure of the coordination compound 1 was determined by single crystal X-ray diffraction. The structure analysis shows that compound 1 is a novel 3D supramolecular network structure, and the central metal adopts the eight-coordination mode to form a double-cap triangular prism spatial configuration. It is worth mentioning that the excellent heat-resisting ability of the framework, which is stable until heated to nearly 400 °C. Meanwhile, the fluorescence sensing test showed that as synthesized compound 2 was a new type of fluorescent probe with high efficiency, high selectivity and has the ability to simultaneously detect a variety of cations and anions (Fe3+, Al3+, Cr3+, C2O4 2?, Cr2O7 2?, MnO4 ?, PO4 3?). Moreover, it owns higher Ksv value (1.77 × 104 M?1, 1.44 × 104 M?1, 3.621 × 104 M?1, 2.07 × 103 M?1, 5.65 × 103 M?1, 3.18 × 103 M?1, 1.82 × 103 M?1, respectively) and a lower detection limit (1.93 μM, 2.38 μM, 0.945 μM, 16.5 μM, 6.06 μM, 10.8 μM, 18.8 μM, respectively). This results in compound 2 being superior to other probes reported previously, and the mechanism of fluorescence quenching was explained to some extent. In addition, during the fluorescence titration experiment, we found an interesting luminescence change of compound 2. Most notably, it emitted white light in DMA solvent under the irradiation of handheld ultraviolet lamp (wavelength: 365 nm) while the solid sample emitted yellow light at the same conditions.
Bifunctional fluorescent quenching detection of 2,4,6-trinitrophenol (TNP) and acetate ions via 4,4′-(9,9-dimethyl-9H-fluorene-2,7-diyl)dibenzoic acid
Ni, Jue Chen,Yan, Jie,Zhang, Li Jing,Shang, Di,Du, Ning,Li, Shuang,Zhao, Jin Xin,Wang, Yang,Xing, Yong Heng
, p. 4978 - 4982 (2016)
The 4,4′-(9,9-dimethylfluorene-2,7-diyl)dibenzoic acid (5) was synthesized using commercial fluorene as the starting material followed by processes of bromination, methylation, Suzuki coupling and hydrolysis. We reported it as an exclusive fluorescence sensor for 2,4,6-trinitrophenol (TNP) and acetate ions for the first time. The experimental results suggested a high efficiency for TNP detection with KSVvalues of 21,215?M?1, which has achieved to micromolar level (10?μM) of this material. Moreover, the detection limit (1.39?×?10?6?M) was measured according to the fluorescence intensity changes of Ac?in CH3CN.
Synthesis of new fluorene compounds for highly selective sensing of picric acid, Fe3+ and L-arginine
Han, Yingying,Huang, Xintong,Hui, Tianqi,Yan, Jie,Yang, Haicheng,Zhao, Jinxin,Zhou, Xinyue
, (2020)
Two compounds, 4-(4-(7-bromo-9, 9-dimethyl-fluoren-2-yl) phenyl) pyridine (4) and 2, 7-Bis-(4-tert-butyl-phenyl)-9,9-dimethyl-9H-fluorene (5), were synthesized by bromination, methylation and Suzuki coupling reaction with fluorene as the starting material. The compounds were used as fluorescent sensors to detect some nitro compounds (NACs), metal cations and amino acids. The test results showed that the 4-(4-(7-bromo-9, 9-dimethyl-fluoren-2-yl) phenyl) pyridine (4) as fluorescence sensor 1 detected 2, 4, 6-Trinitrophenol (TNP) at the magnitude of 10 μM, with a sensitivity of Ksv was 4.6 × 105 M?1 and the detection limit was 6.9 × 10?7 M. The sensitivity detection for Fe3+ with Ksv value was 1.4 × 105 M?1, and the detection limit was 3.6 × 10?7 M. At the same time, it was found that 2, 7-Bis-(4-tert-butyl-phenyl)-9,9-dimethyl-9H-fluorene (5) as fluorescence sensor 2 also showed excellent selective recognition ability toward the arginine (L-arg) in biomolecules with Ksv values of 3.9 × 10 4 M?1, and the detection limit was 1.15 × 10?6 M for arginine (L-arg).
Self-repairing platinum metal gel material as well as preparation method and application thereof
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Paragraph 0126-0127, (2021/11/21)
The invention discloses a self-repairing platinum metal gel and a preparation method and application thereof, and belongs to the field of self-repair metal gel materials. A self-healing platinum metal gel Pt-4 CHO, having the structure of Formula I, by performing a series of substitution reactions to the feedstock 2, 7 - dibromo - 9H - fluorene. With sonogashira-and CHO aldehyde group conversion into imine-based synthetic model molecule Pt 4 Pt 4 Pt-4 imine through Schiff base reaction, the prepared platinum metal gel has good self-repairing property, optical transparency, mechanical property and light-limiting property, and laser protection performance is further improved due to nonlinear scattering of laser in the gel.
Emission color-tunable oxazol(in)yl-substituted excited-state intramolecular proton transfer (ESIPT)-based luminophores
Bigall, Nadja C.,Duvinage, Daniel,G?bel, Dominik,Nachtsheim, Boris J.,Rusch, Pascal
supporting information, p. 15430 - 15433 (2020/12/25)
Oxazolinyl- and arylchalcogenazolyl-substituted hydroxyfluorenes exhibiting excited-state intramolecular proton transfer (ESIPT) are described as potent and highly modular luminophores. Emission color tuning was achieved by varying the π-expansion and the
Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization
Friedrich, Marius,G?bel, Dominik,Lork, Enno,Nachtsheim, Boris J.
supporting information, p. 1683 - 1692 (2021/06/25)
Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.
Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
G?bel, Dominik,Clamor, Nils,Lork, Enno,Nachtsheim, Boris J.
supporting information, p. 5373 - 5377 (2019/06/07)
The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.
Crystal structure and mesogenic behaviour of a new fluorene derivative: 9,9-dimethyl-2,7-bis(4-pentylphenyl)-9H-fluorene
Gupta, Sakuntala,Choudhury, Tanmay,Dmochowska, Ewelina,Kula, Przemyslaw,Borbone, Fabio,Centore, Roberto
, p. 1459 - 1464 (2019/11/14)
The title compound, C37H42, is a new mesogenic compound containing the fluorene moiety. It exhibits enantiotropic nematic liquid crystalline behaviour with melting at 125 °C and isotropization at 175 °C. The crystallographically independent unit contains two molecules oriented face-to-edge with respect to each other. The two molecules have nearly the same conformation of the bis-phenyl fluorene moiety. The molecular packing in the crystal phase is nematic-like.
Fluorene-containing compound and organic light emitting device with same
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Paragraph 0075-0076; 0078, (2018/09/11)
The invention provides a fluorene-containing compound and an organic light emitting device with the same, and relates to the technical field of organic photoelectric materials. The fluorene-containingcompound and the organic light emitting device have the advantages that fluorene bodies are connected with arylamine and substituted or unsubstituted aromatic nucleus condensed imidazole derivativesto obtain the fluorene-containing compound, the fluorene-containing compound is a bipolar transmission material, is favorable for composition of holes and electrons in luminescent layers, is good in stability and luminescent efficiency and easy to synthesize and operate and can be applied to the organic light emitting device to be used as a doping material for luminescent layers, accordingly, theproblems of low luminescent efficiency and short service lives of blue luminescent materials in existing organic light emitting devices can be effectively solved, and the organic light emitting deviceis high in luminescent efficiency and long in service life.
