16218-28-3Relevant articles and documents
Siloles and acetenyl aromatics copolymers: Synthesis, characterization and photophysical properties
He, Zhenhua,Lai, Guoqiao,Li, Zhifang,Yuan, Xiao,Shen, Yongjia,Wang, Chengyun
, p. 550 - 558 (2015)
Two copolymers, poly(1,1-dimethyl-3,4-diphenylsilole-alt-N-hexyl-3,6-diethynylcarbazole) (PS-DyCz) and poly(1,1-dimethyl-3,4-diphenylsilole-alt-2,7-diethynyl-9,9′-dihexylfluorene) (PS-DyF), were synthesized by Sonogashira coupling reaction of 2,5-dibromo-
α-Cyanostilbene and fluorene based bolaamphiphiles: Synthesis, self-assembly, and AIEE properties with potential as white-light emissive materials and light-emitting liquid crystal displays
Zhang, Deling,Liu, Yuantao,Gao, Hongfei,Chang, Qing,Cheng, Xiaohong
, p. 17474 - 17481 (2020)
Novel bolaamphiphiles containing two α-cyanostilbene units interconnected with 2,7-substituted-9,9-dialkylated fluorene as the central core and a diol unit at each terminal have been synthesized efficiently by a palladium catalyzed Suzuki coupling reaction and the Knoevenagel condensation reaction as key steps. POM, DSC and XRD investigation reveals that these compounds can organize into single wall triangular honeycomb columnar phases. A unique packing model was established in which the twisted π-conjugated backbones stacked alternatively into the walls and were connected through the end diol groups to form a triangular honeycomb, and the almost perpendicularly distributed alkyl side chains filled the cells. Such packing was additionally stabilized by the local anti-parallel dipole interactions of α-cyanostilbene and the H-bonding between CN?H. These compounds showed the AIEE effect and emitted yellow luminescence which could be further utilized to generate white light emission by coating on a commercially available blue LED lamp. Additionally, light-emitting liquid crystal display (LE-LCD) device could be obtained by dissolution of such AIE active distinctive luminogens in commercially available nematic LCs.
Ultrafine fluorene-pyridine oligoelectrolyte nanoparticles for supersensitive fluorescence sensing of heparin and protamine
Du, Huifeng,He, Xiaoxiao,Huang, Hongmei,Mao, Wensheng,Wang, Kemin,Xiao, Yi,Zhang, Li,Zhang, Youyu,Zhao, Yaqian
, p. 8304 - 8307 (2021)
A new fluorene-pyridine oligoelectrolyte (OFP) is rationally proposed and readily synthesized via a simple one-pot Sonogashira approach. Hence, an unexpectedly small cationic oligomer nanosensor (i.e. OFPNPs, ～ 1.2 nm in diameter) was conveniently fabricated owing to the enhanced flexibility endowed by the meta-substituted pyridyl unit. Inspiringly, this facile nanoplatform with low cytotoxicity favors the ultrasensitive fluorescence assay for heparin and protamine with a detection limit (LOD, S/N = 3) as low as 1.2 ng mL-1 and 0.5 ng mL-1, respectively, involving heparin-induced aggregation of OFPNPs through electrostatic interaction or competitive rebinding of protamine to heparin. This journal is
Strong enhancement of two-photon absorption properties in synergic 'semi-disconnected' multiporphyrin assemblies designed for combined imaging and photodynamic therapy
Mongin, Olivier,Sankar, Muniappan,Charlot, Marina,Mir, Youssef,Blanchard-Desce, Mireille
, p. 6474 - 6478 (2013)
The synthesis and photophysical properties of new multiporphyrin assemblies are described. Their design, based on a smooth electronic disconnection between two-photon absorbing (2PA) octupolar or quadrupolar cores and the peripheral porphyrins, leads to a
Highly Luminescence Anthracene Derivatives as Promising Materials for OLED Applications
Slodek, Aneta,Filapek, Michal,Schab-Balcerzak, Ewa,Grucela, Marzena,Kotowicz, Sonia,Janeczek, Henryk,Smolarek, Karolina,Mackowski, Sebastian,Malecki, Jan Grzegorz,Jedrzejowska, Agnieszka,Szafraniec-Gorol, Grazyna,Chrobok, Anna,Marcol, Beata,Krompiec, Stanislaw,Matussek, Marek
, p. 4020 - 4031 (2016)
Novel symmetrical anthracene derivatives with bulky carbazolyl-fluorene, diphenylamino-fluorene, or carbazolyl-carbazole units connected to the anthracene frame through an ethynyl bridge were synthesized in excellent yield by using Sonogashira cross-coupling. The ethynyl bridge in the anthracene dyes increases π-electron conjugation and the bulky substituents considerably attenuate intermolecular interactions. The dyes possess high thermal stability, tremendous solubility in common organic solvents, and especially high photoluminescence quantum yield (Φf) in solution in the range of 77–98 %. OLED devices were fabricated. The AFM images of thin films and blends prepared from all compounds show a uniform and flat surface, indicating excellent film-forming properties. Devices incorporating the anthracene derivative with diphenylamino-fluorene end-capping groups exhibited the highest value of current density (J). All of the fabricated OLED devices emitted yellowish-orange light under applied voltage.
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)
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 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)
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.
Synthesis of cationic diacetylene-co-carbazole-co-fluorene polymers and their sensitive fluorescent quenching properties with DNA
Zeng, Wennan,Liu, Shouping,Zou, Hanxun,Wang, Linyun,Beuerman, Roger,Cao, Derong
, p. 4168 - 4177 (2010)
Two neutral precursor conjugated copolymers based 2,7-diethynylfluorene and 3,6-diethynylcarbazole units in the main chain (PFC and PF2C) were prepared by Hay coupling polymerization. Their cationic copolymers (CPFC and CPF2C) were prepared by the methylation of their diethylpropylamino groups with CH 3I. For comparison, neutral conjugated homopolymers of 2,7-diethynylfluorene (PF), 3,6-diethynylcarbazole units (PC) and their cationic polymers (CPF and CPC) were also prepared with the same method. A comparative study on the optical properties of cationic polymers CPFC and CPF2C in DMF and DMF/H2O showed that they underwent water-induced aggregation. The spectral behaviors of CPFC and CPF2C with calf thymus DNA showed that a distinct fluorescent quenching took place with minute addition of CT DNA (3.3 × 10-13 M). The results showed that the polymers would be promising biosensor materials for sensitive detection of DNA.
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)
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.
Selective dispersion of single-walled carbon nanotubes with electron-rich fluorene-based copolymers
Liang, Shuai,Subrahmanyam, Ayyagari V.,Khadem, Mohammadreza,Zhao, Yuming,Adronov, Alex
, p. 25733 - 25740 (2016)
We herein report the design and synthesis of novel fluorene-based π-conjugated copolymers containing electron-donating dithiafulvene (DTF) and π-extended tetrathiafulvalene (exTTF) repeat units through Suzuki coupling polymerization. The resulting copolymers showed a comparable degree of polymerization and retained the redox activity originating from the DTF and exTTF building blocks. Theoretical modeling studies predicted that these electron-rich copolymers could wrap around individual single-walled carbon nanotubes (SWNTs) via intimate π-stacking, while experimental results confirmed that the copolymers formed stable polymer-SWNT supramolecular complexes in organic solvents with high selectivity for semiconducting SWNTs. Various spectroscopic and microscopic analyses were conducted to show that the electronic nature of conjugated polymer backbones plays an important role in tuning the binding preference of the polymers for particular types of SWNTs, offering an efficient and selective non-covalent method to sort SWNTs from as-produced mixtures.
