278176-06-0Relevant academic research and scientific papers
Blue light material composed of acetylene bridged fluorene and anthracene derivatives and preparation method thereof
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Paragraph 0035; 0040-0042, (2020/03/29)
The invention belongs to the technical field of blue-light emitting material preparation, and discloses an acetylene bridged fluorene and anthracene derivative blue-light emitting material and a preparation method thereof. The method comprises the following steps: a compound intermediate product 2, a compound intermediate product 3, Pd(PPh3)2Cl2, CuI, PPh3 and a magnetic stirring bar are added into a single-necked flask with a volume of 250mL, and vacuumizing and nitrogen introducing are repeated for 4 times; under the protection of a nitrogen gas, a mixed solvent subjected to oxygen removal by introducing a nitrogen gas for 30min is added by a syringe, and a reaction is performed for 48h under a nitrogen gas atmosphere; the reaction is stopped, filtration is performed, filter residues arewashed for 3 times with toluene, a filtrate is separately washed twice with water and saturated brine, drying is performed by anhydrous sodium sulfate for overnight, and a solvent is evaporated to dryness to obtain a crude product; and the crude product is subjected to chromatography by applying a silica gel column, concentration is performed, the concentrated material is dropped into absolute methanol for recrystallization, and therefore the yellow solid is obtained. According to the invention, two n-octyl long aliphatic chains on fluorene can increase the solubility of the material in an organic solvent, and the acetylene linked fluorene and anthracene structure can increase the conjugacy and rigidity of the material.
One-pot synthesis of benzofluorene fused aromatic hydrocarbons
Dong, Wendan,Hu, Zhun,Wang, Ziqi,Sun, Bing,Zhang, Xueqiong,Zhang, Fang-Lin
supporting information, (2019/11/13)
A new and efficient synthetic approach for the one-pot construction of benzofluorene fused aromatic hydrocarbons was developed via a transient-directing group strategy. The palladium-catalyzed cascade reaction proceeded via consecutive arylation, cyclization and aromatization steps. Moderate to good yields along with broad functional group tolerance were achieved under mild reaction conditions.
Functional phenylethynylene side arm poly(arylene ethynylene) conjugated polymers: Optical and electrochemical behavior for enrichment of electronic applications
Arun Kumar,Gomathi Priya,Alagar
supporting information, p. 5767 - 5773 (2018/04/23)
The poly(arylene ethynylene) (PAE) conjugated polymers (CPs) with a donor-acceptor (D-A) side arm have been designed and synthesized using Sonogashira cross coupling in the presence of cyano methylene, or cyano thiophene gave diethynyl (A) and alkoxy and alkyl substituted diiodo aryl monomers (D). An interesting electronic response in optical measurements such as UV-visible (UV-vis) and fluorescence (FL) spectra was observed in tetrahydrofuran solvent. From the FL spectra, it was observed that the CP solutions possess an interesting long bathochromic shift when compared with the UV-vis spectra, because of the electron withdrawing, electron releasing and conjugation effects. The electrochemical and thin film UV-vis spectral measurements provided highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) electronic energy levels and their corresponding semiconducting electronic energy gaps (Eg) of the PAE CPs. Among the side arm CPs, polymers P1 and P5 have low Eg of 2.14 eV and 2.17 eV. The new PAE CPs are reliable for use in electronic and photonics applications.
Synthesis and photophysical properties of new perylene bisimide derivatives for application as emitting materials in OLEDs
Matussek, Marek,Filapek, Micha?,Gancarz, Pawe?,Krompiec, Stanis?aw,Grzegorz Ma?ecki, Jan,Kotowicz, Sonia,Siwy, Mariola,Ma?kowski, Sebastian,Chrobok, Anna,Schab-Balcerzak, Ewa,S?odek, Aneta
, p. 590 - 599 (2018/07/29)
Three novel perylene diimide derivatives with bulky aromatic moieties (fluorene, carbazolyl-fluorene, and anthracyl-fluorene) connected via triple bonds with perylene core were successfully designed and synthesized. The chemical structure of prepared compounds was confirmed by 1H and 13C NMR and mass spectrometry. Their optimized ground-state geometry and frontier molecular orbitals were theoretically estimated based on density functional theory. The compounds undergo the reversible electrochemical reduction process and exhibit very low energy band gaps (1.56–1.98 eV) being promising for electronic applications. They also display excellent solubility, high thermal stability and luminescence in solution and in the solid state as a film in the red spectral region. The highest photoluminescence quantum yield (79% in solution and 28% in the film) was found for perylene diimide bearing fluorene unit. All molecules showed the ability for light emission under an applied voltage. The fabricated diodes with structure ITO/PEDOT:PSS/compound/Al exhibited electroluminescence with maximum emission band located between 685 and 732 nm. The most intense electroluminescence, which was additionally plasmonically enhanced by incorporating silver nanowires, was observed for the device based on molecules with anthracene structure.
Meta - And para -Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions
Hempe, Matthias,Schnellb?cher, Lutz,Wiesner, Tobias,Reggelin, Michael
, p. 4489 - 4499 (2017/09/26)
Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9 H -fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9 H -fluorenes that underwent end-functionalization by the Suzuki-Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9 H -fluorenes. Novel meta -functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta -substituted materials than their para -functionalized analogues.
Achieving yellow emission by varying the donor/acceptor units in rod-shaped fluorenyl-alkynyl based π-conjugated oligomers and their binuclear gold(i) alkynyl complexes
Islam, Sk Najmul,Sil, Amit,Patra, Sanjib K.
supporting information, p. 5918 - 5929 (2017/07/11)
Fluorenyl-alkynyl based π-conjugated rod-shaped oligomers bearing different central aromatic moieties and functionalizable di-alkynyl termini, such as H - Fl - Fl - Fl - H (OH1), H - Fl - Btz - Fl - H (OH2) and H - Fl - Btd - Fl - H (OH3) where Fl = 9,9-d
The influence of experimental conditions and intermolecular interaction on the band gap determination. Case study of perylene diimide and carbazole-fluorene derivatives.
Filapek, Micha?,Matussek, Marek,Szlapa, Agata,Kula, Slawomir,Paj?k, Micha?
, p. 449 - 456 (2016/09/23)
The perylene diimide and carbazole-fluorene derivatives are intensively investigated in organic electronic and photovoltaic applications. However, they intermolecular interactions vary considerably. Herein, we present a systematic UV–vis spectroscopy and electrochemical study of intermolecular interaction influence on determination of HOMO, LUMO and band gap. The influence of this type of interactions on photophysical properties with the aid of NMR spectroscopy and DFT calculations was examined. Effect of the electrode type was investigated as well. The cyclic voltammetry results obtained at different species concentrations (including solid state measurements) were compared. We have found that when interactions are strong differences in determined bang gap are significant. Contrary to half wave potential, peak onset was found to be concentration independent. Finally, we have observed that comparison of values from solid state measurement and carried out for diluted species can introduce high inconsistencies in determination of structure/property relationships.
Synthesis of π-Bridged Dually-Dopable Conjugated Polymers from Benzimidazole and Fluorene: Separating Sterics from Electronics
Harris, Jared D.,Liu, Jiakai,Carter, Kenneth R.
, p. 6970 - 6977 (2015/10/28)
We describe the synthesis and characterization of three new alternating copolymers containing fluorene and a dually dopable benzimidazole moiety. Poly(2-n-heptyl-benzimidazole-alt-9,9-di-n-octylfluorene) (PBIF), poly(2-n-heptyl-benzimidazole-vinylene-9,9-
Synthesis and tunable chiroptical properties of chiral BODIPY-based D-π-A conjugated polymers
Ma, Xiao,Azeem, Eman Abdel,Liu, Xiaolin,Cheng, Yixiang,Zhu, Chengjian
, p. 1076 - 1084 (2014/02/14)
Three novel donor-π-acceptor (D-π-A) type chiral polymers P1, P2, and P3 could be synthesized from diiodo-substituted chiral boron-dipyrromethene (BODIPY) derivative (M-1) with 2,7-diethynyl-9,9-dioctyl-9H-fluorene (M-2), 3,6-diethynyl-9-octyl-9H-carbazol
Sterically encumbered bipyridyl-derivatized conjugated polymers and metallopolymers incorporating phenylenevinylene, phenyleneethynylene, and fluorenylene segments
He, Susan,Buelt, Ashley A.,Hanley, Jessica M.,Morgan, Brad P.,Tennyson, Andrew G.,Smith, Rhett C.
, p. 6344 - 6352 (2012/10/30)
This work reports the preparation of a series of 2,2′-bipyridyl (bipy) modified π-conjugated polymers having an average of one or three monomer units (p-arylene ethynylene for PPE1 and PPE3 or 7,7-dihexylfluorene for PF1 and PF3) between metal-binding sites. Spectroscopic data demonstrate that strategic placement of sterically encumbered mesityl groups about the metal binding sites enforces a 1:1 metal to bipy binding ratio. This steric coordination control ensures that the metalated polymers remain solution processable rather than forming insoluble networks via coordinative cross-linking. The solution photophysical and electrochemical properties of metal-free and metalated materials are reported and compared with those of related conjugated polymers and conducting metallopolymers.
