- Polyphenol derivatives of porphyrins containing fluorene units: Synthesis and positive-tone photoresists for 22-nanometer lithography
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A new strategy was proposed for the synthesis of polyphenol derivatives of fluorene-containing porphyrins to be used as the base for positive-tone photoresists for lithography with exposure at 13.5 nm wavelength, which allow fabrication of microchips with a size of down to 22 nm. Polyphenols based on fluorenecontaining porphyrins were synthesized for the first time. It was shown that these polyphenol derivatives can be used to obtain positive-tone photoresists with a resolution of 22 nm.
- Vainer, A. Ya.,Dyumaev,Kovalenko,Babuskin, Ya. L.,Krichevskaya,Lubenskii
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- Donor-Pi-Acceptor Fluorene Conjugates, Based on Chalcone and Pyrimidine Derivatives: an Insight into Structure-Property Relationship, Photophysical and Electrochemical Properties
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A small set of four new fluorenyl chromophores (5-5a-c) was accomplished by stepwise nucleophilic substitution, Friedel-Crafts acylation, Ullman coupling, aldol condensation and cyclization reactions. The fluorene moiety was substituted at 2,7,9 and 9′ positions with diverse groups. The synthesized derivatives were characterized by FTIR, 1H-NMR and 13C-NMR spectroscopic techniques. The optical properties were evaluated by by UV-VIS absorption and Fluorescence studies. HOMO and LUMO energy levels were evaluated by electrochemical studies and were found at ?5.37-5.83 eV and ? 2.47-2.94 eV respectively with band gap energy values 2.88 to 2.91 eV. The band gap energy values suggested that these synthesized molecules can be manipulated in the designing of blue and green OLEDS. [Figure not available: see fulltext.].
- Belfield, Kevin D.,Channar, Pervaiz Ali,Irfan, Madiha,Mahar, Jamaluddin,Saeed, Aamer,Shabir, Ghulam,Ul-Hamid, Anwar
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- An investigation of the effect of conjugation on fluorene based chromophores; Optoelectronic and electrochemical behavior
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The requisition of small light emitting organic molecules is on the rise in the field of organic electronics. This study is aimed at synthesis of fluorene based chromophores which possess promising optoelectronic properties. The characterization of synthesized derivatives was carried out by spectroscopy (1H-NMR and 13C-NMR) and spectrometry (EI-MS). The optical properties evaluated by using UV-Vis spectroscopy, were from 394 to 420 nm, Fluorescence ranged 48 nm-113 nm, HOMO energy levels are ?6.75 eV to ?7.15 eV LUMO -4.08 to ?4.52eV with a band gap energy values 2.63–2.67 eV. The band gap energy values suggest that these synthesized molecules can be manipulated in the designing of blue and green OLEDS.
- Mahar, Jamaluddin,Saeed, Aamer,Belfield, Kevin D.,Iqbal, Anila,Irfan, Madiha,Shabir, Ghulam,Larik, Fayaz Ali,Channar, Pervaiz Ali
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- Bio-inspired enol-degradation for multipurpose oxygen sensing
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Inspired by the enol-degradation of luciferin, a new oxygen sensor with oppositely changed color and fluorescence has been designed. This new reaction-based dual mode sensor can not only be used as a highly selective instant "fluorescence on" oxygen probe, but also as a freshness indicator of food or food materials by using its property of time-adjustable color fading.
- Zhang, Yu-Mo,Wang, Xiaojun,Li, Wen,Zhang, Weiran,Li, Minjie,Zhang, Sean Xiao-An
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Read Online
- Solid-state construction of zigzag periphery: Via intramolecular C-H insertion induced by alumina-mediated C-F activation
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Caryl-F bond activation has become an important and quickly developing method for construction of carbon-based materials. We report that alumina-mediated C-F bond activation (AmCFA) enables construction of PAHs with zigzag periphery. This method includes
- Akhmetov, Vladimir,Amsharov, Konstantin,F?rtsch, Andreas,Feofanov, Mikhail
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supporting information
p. 12325 - 12328
(2021/11/30)
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- APEX Strategy Represented by Diels–Alder Cycloadditions—New Opportunities for the Syntheses of Functionalised PAHs
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Diels–Alder cycloaddition of various dienophiles to the bay region of polycyclic aromatic hydrocarbons (PAHs) is a particularly effective and useful tool for the modification of the structure of PAHs and thereby their final properties. The Diels–Alder cycloaddition belongs to the single-step annulative π-extension (APEX) reactions and represents the maximum in synthetic efficiency for the constructions of π-extended PAHs including functionalised ones, nanographenes, and π-extended fused heteroarenes. Herein we report new applications of the APEX strategy for the synthesis of derivatives of 1,2-diarylbenzo[ghi]perylene, 1,2-diarylbenzo[ghi]perylenebisimide and 1,2-disubstituted-benzo[j]coronene. Namely, the so far unknown cycloaddition of 1,2-diarylacetylenes into the perylene and perylenebisimide bay regions was used. 1,2-Disubstituted-benzo[j]coronenes were obtained via cycloaddition of benzyne into 1,2-diarylbenzo[ghi]perylenes by using a new highly effective system for benzyne generation and/or high pressure conditions. Moreover, we report an unprecedented Diels–Alder cycloaddition–cycloaromatisation domino-type reaction between 1,4-(9,9-dialkylfluoren-3-yl)-1,3-butadiynes and perylene. The obtained diaryl-substituted core-extended PAHs were characterised by DFT calculation as well as electrochemical and spectroscopic measurements.
- Kurpanik, Aneta,Matussek, Marek,Szafraniec-Gorol, Gra?yna,Filapek, Micha?,Lodowski, Piotr,Marcol-Szumilas, Beata,Ignasiak, Witold,Ma?ecki, Jan Grzegorz,Machura, Barbara,Ma?ecka, Magdalena,Danikiewicz, Witold,Pawlus, Sebastian,Krompiec, Stanis?aw
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supporting information
p. 12150 - 12157
(2020/09/01)
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- Preparation method of photoelectric material intermediate (by machine translation)
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The invention discloses a preparation method of a photoelectric material intermediate, and is not reported in China at present. To the preparation method provided by the invention, the raw 2 material fluorene -9 is used as a series of operations such as single iodination and the C-N acenyman coupling, crude purification 9 and 9 - the like 4 -2 - 99.0%. The preparation method provided by the invention is simple to operate and suitable for industrial production. (by machine translation)
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Paragraph 0008; 0012; 0013
(2019/10/08)
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- Synthesis and photophysical properties of new perylene bisimide derivatives for application as emitting materials in OLEDs
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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.
- 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
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p. 590 - 599
(2018/07/29)
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- 4′-Phenyl-2,2′:6′,2″-terpyridine derivatives-synthesis, potential application and the influence of acetylene linker on their properties
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Novel derivatives of 4'-phenyl-2,2':6′,2″-terpyridine (tpy) with ethynyl (T1), 2-ethynyl-9,9-dioctylfluorene (T2), 9,9-dioctylfluorene (T3), 9-ethynyl-10-decyloxyanthracene (T4) substituents were obtained via Sonogashira or Suzuki-Miyaura coupling reactions, respectively, and thoroughly characterized. The presence of ethynyl bridge impacts photophysical properties of novel compounds by shifting absorption and emission spectra towards longer wavelengths as compared to T3, where fluorene is connected with tpy via a single bond. TGA measurements showed that among the new terpyridines those obtained as solids exhibited high thermal stability as opposed to those which were oils (tpy containing fluorene motif). Due to the fact that high thermal stability of 4'-phenyl-2,2':6′,2″-terpyridine derivatives showed photoluminescence (PL) quantum yield (Φ) in the range of 27–84% in solution, their electroluminescence ability was tested in diodes with guest-host configuration. For the compounds dispersed in a matrix consisting of poly(9-vinylcarbazole) (PVK) (50 wt %) and (2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole) (PBD) (50 wt %) radiation with maxima between 374 and 531 nm and characterized with Φ in the range of 8–12% was observed. They exhibited green or violet electroluminescence. The results confirmed the substantial role of aryl groups and the linker in the presented terpyridines in terms of their thermal, electrochemical, optical and electroluminescence properties. In addition, density functional theory (DFT) and time-dependent-density functional theory (TD-DFT) calculations were performed to provide an independent support and deeper insight into the experimental results.
- Zych, Dawid,Slodek, Aneta,Matussek, Marek,Filapek, Micha?,Szafraniec-Gorol, Gra?yna,Ma?lanka, S?awomir,Krompiec, Stanis?aw,Kotowicz, Sonia,Schab-Balcerzak, Ewa,Smolarek, Karolina,Ma?kowski, Sebastian,Olejnik, Marian,Danikiewicz, Witold
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p. 331 - 343
(2017/07/24)
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- Design, synthesis, and evaluation of potent Wnt signaling inhibitors featuring a fused 3-ring system
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The Wnt signaling pathway is a critical developmental pathway which operates through control of cellular functions such as proliferation and differentiation. Aberrant Wnt signaling has been linked to the formation and metastasis of tumors. Porcupine, a member of the membrane-bound O-acyltransferase family of proteins, is an important component of the Wnt pathway. Porcupine catalyzes the palmitoylation of Wnt proteins, a process needed for their secretion and activity. Here we report a novel series of compounds obtained by a scaffold hybridization strategy from a known porcupine inhibitor class. The leading compound 59 demonstrated subnanomolar inhibition of Wnt signaling in a paracrine cellular assay. Compound 59 also showed excellent chemical, plasma and liver microsomal stabilities. Furthermore, compound 59 exhibited good pharmacokinetic profiles with 30% oral bioavailability in rat. Collectively, these results strongly support further optimization of this novel scaffold to develop better Wnt pathway inhibitors.
- Xu, Zhixiang,Li, Jiajun,Wu, Yiyuan,Sun, Zhijian,Luo, Lusong,Hu, Zhilin,He, Sudan,Zheng, Jiyue,Zhang, Hongjian,Zhang, Xiaohu
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p. 154 - 165
(2015/12/04)
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- Synthesis and dye sensitized solar cell applications of Bodipy derivatives with bis-dimethylfluorenyl amine donor groups
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Three Bodipy dyes with strong absorptivities in the visible and near infrared regions were designed, synthesized and their potential as photosensitizers for liquid electrolyte-based dye sensitized solar cells have been evaluated. For the first time Bodipy derivatives with bis-dimethylfluorenyl amine donor groups which were known for their bulky structures as donor groups have been used together. We altered our mostly used triphenylamine group with these and investigated the dye-sensitized solar cell efficiencies of this new class of Bodipy dyes.
- ?akmak, Yusuf,Kolemen, Safacan,Buyuktemiz, Muhammed,Dede, Yavuz,Erten-Ela, Sule
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p. 4086 - 4092
(2015/05/20)
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- Copper-promoted reductive coupling of aryl iodides with 1,1,1-trifluoro-2-iodoethane
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An efficient Cu-promoted reductive coupling of aryl iodides with 1,1,1-trifluoro-2-iodoethane has been developed. This reaction could occur in good yields under milder conditions as compared with previous studies. The reaction tolerated nitro, formyl, ester, ether, carbonyl, sulfonyl, and even azo groups.
- Xu, Song,Chen, Huan-Huan,Dai, Jian-Jun,Xu, Hua-Jian
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supporting information
p. 2306 - 2309
(2014/05/20)
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- Stepwise co-sensitization as a useful tool for enhancement of power conversion efficiency of dye-sensitized solar cells: The case of an unsymmetrical porphyrin dyad and a metal-free organic dye
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A tertiary arylamine compound (DC), which contains a terminal cyano-acetic group in one of its aryl groups, and an unsymmetrical porphyrin dyad of the type Zn[Porph]-L-H2[Porph] (ZnP-H2P), where Zn[Porph] and H2[Porph] are metallated and free-base porphyrin units, respectively, and L is a bridging triazine group functionalized with a glycine moiety, and were synthesized and used for the fabrication of co-sensitized dye-sensitized solar cells (DSSCs). The photophysical and electronic properties of the two compounds revealed spectral absorption features and frontier orbital energy levels that are appropriate for use in DSSCs. Following a stepwise co-sensitization procedure, by immersing the TiO2 electrode in separate solutions of the dyes in different sequence, two co-sensitized solar cells were obtained: devices C (ZnP-H2P/DC) and D (DC/ZnP-H 2P).The two solar cells were found to exhibit power conversion efficiencies (PCEs) of 6.16% and 4.80%, respectively. The higher PCE value of device C, which is also higher than that of the individually sensitized devices based on the ZnP-H2P and DC dyes, is attributed to enhanced photovoltaic parameters, i.e. short circuit current (Jsc = 11.72 mA/cm2), open circuit voltage (Voc = 0.72 V), fill factor (FF = 0.73), as it is revealed by photovoltaic measurements (J-V curves) and by incident photon to current conversion efficiency (IPCE) spectra of the devices, and to a higher total dye loading. The overall performance of device C was further improved up to 7.68% (with Jsc = 13.45 mA/cm2, Voc = 0.76 V, and FF = 0.75), when a formic acid treated TiO 2 ZnP-H2P co-sensitized photoanode was employed (device E). The increased PCE value of device E has been attributed to an enhanced Jsc value (=13.45 mA/cm2), which resulted from an increased dye loading, and an enhanced Voc value (=0.76 V), attributed to an upward shift and increased of electron density in the TiO 2 CB. Furthermore, dark current and electrochemical impedance spectra (EIS) of device E revealed an enhanced electron transport rate in the formic acid treated TiO2 photoanode, suppressed electron recombination at the photoanode/dye/electrolyte interface, as well as shorter electron transport time (τd), and longer electron lifetime (τe).
- Sharma,Zervaki,Angaridis,Vatikioti,Gupta,Gayathri,Nagarjuna,Singh, Surya Prakash,Chandrasekharam,Banthiya, Ajita,Bhanuprakash,Petrou,Coutsolelos
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p. 1324 - 1337
(2014/05/06)
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- Compounds having hole conducting property, co-adsorbent body comprising same, and dye-sensitized solar cell comprising the co-adsorbent body
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An object of the present invention is to provide a novel concept coadsorbent that can be used instead of conventionally-used deoxycholic acid (DCA). The present invention provides a coadsorbent having hole conduction characteristics, including the compound represented by Formula 3, and provides a dye-sensitized solar cell including a light absorbing layer including the coadsorbent having hole conduction characteristics. The photocurrent and photovoltage of the dye-sensitized solar cell can be improved because it includes a light absorbing layer including the coadsorbent having hole conduction characteristics.
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Paragraph 0035; 0068; 0069
(2014/04/04)
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- A zinc porphyrin sensitizer modified with donor and acceptor groups for dye-sensitized solar cells
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In this article, we have designed and synthesized a novel donor-π-acceptor (D-π-A) type porphyrin-based sensitizer (denoted UI-5), in which a carboxyl anchoring group and a 9,9-dimethyl fluorene were introduced at the meso-positions of porphyrin ring via phenylethynyl and ethynyl bridging units, respectively. Long alkoxy chains in ortho-positions of the phenyls were supposed to reduce the degree of dye aggregation, which tends to affect electron injection yield in a photovoltaic cell. The cyclic voltammetry was employed to determine the band gap of UI-5 to be 1.41 eV based on the HOMO and LUMO energy levels, which were estimated by the onset oxidation and reduction potentials. The incident monochromatic photon-to-current conversion efficiency of the UI-5 DSSC assembled with double-layer (20 nm-sized TiO2/400 nm-sized TiO2) film electrodes appeared lower upon overall ranges of the excitation wavelengths, but exhibited a higher value over the NIR ranges (λ = 650-700 nm) compared to the common reference sensitizer N719. The UI-5-sensitized cell yielded a relatively poor device performance with an overall conversion efficiency of 0.74% with a short circuit photocurrent density of 3.05 mA/cm2, an open circuit voltage of 0.54 mV and a fill factor of 0.44 under the standard global air mass (AM 1.5) solar conditions. However, our report about the synthesis and the photovoltaic characteristics of a porphyrin-based sensitizer in a D-π - A structure demonstrated a significant complex relationship between the sensitizer structure and the cell performance.
- Lee, Seewoo,Sarker, Ashis K.,Hong, Jong-Dal
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p. 3052 - 3058
(2014/12/11)
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- Triarylamine-based dual-function coadsorbents with extended π-conjugation aryl linkers for organic dye-sensitized solar cells
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Triarylamine-based dual-function coadsorbents containing a carboxylic acid acceptor linked by extended π-conjugation aryl linkers (e.g., phenylene: HC-A3, naphthalene: HC-A4 and anthracene: HC-A5) were newly designed and synthesized. They were used as coadsorbents in organic dye-sensitized solar cells (DSSCs) based on a porphyrin dye (hexyloxy-biphenyl-ZnP-CN-COOH (HOP)). For comparison, the π-conjugated phenyl linker (HC-A3) previously developed by our group was also used as a coadsorbent. The structural effects on the photophysical and electrochemical properties and DSSC performance were systematically investigated. As a result, the DSSCs based on HC-A4 and HC-5 displayed power conversion efficiencies (PCEs) of 8.2% and 5.1%, respectively, while the HC-A3-based DSSC achieved a PCE of 7.7%. In the case of HC-A4, both the short-circuit photocurrent densities (Jsc) and open-circuit voltages (Voc) of DSSCs were simultaneously improved to a large extent due to the more effective prevention of π-π stacking of organic dye molecules and the better light-harvesting effect at short wavelengths. The HC-A5-based DSSC exhibited a much lower short-circuit current (Jsc) and open-circuit voltages (Voc) compared to the HC-A4-based DSSC, due to the fact that the dihedral angle of the π-conjugated linkers was too high for electron injection into the TiO2 conduction band (CB) level. This had a reduced effect on preventing the π-π stacking of dye molecules, resulting in lower Jsc and Voc values.
- Choi, In Taek,You, Ban Seok,Eom, Yu Kyung,Ju, Myung Jong,Choi, Won Seok,Kang, Sung Ho,Kang, Min Soo,Seo, Kang Deuk,Hong, Ji Yeoun,Song, Sang Hyun,Yang, Ji-Woon,Kim, Hwan Kyu
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supporting information
p. 3316 - 3326
(2015/02/19)
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- Platinum(II) complexes bearing 2-(9,9-dihexadecyl-7-R-fluoren-2-yl)-1,10- phenanthroline ligands: Synthesis, photophysics and reverse saturable absorption
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Six platinum(II) complexes bearing 2-(9,9-dihexadecyl-7-R-fluoren-2-yl)-1, 10-phenanthroline ligands (R = NO2, CN, I, H, benzothiazole, thiophene for ligands 1-6, respectively) were synthesized and their photophysics and reverse saturable absorption (RSA) were systematically investigated. All complexes exhibit intense absorption bands between 350 and 450 nm, which are attributed to 1π,π/1ILCT (intraligand charge transfer) transitions, and broad 1MLCT (metal to ligand charge transfer) transitions between 475 and 550 nm. All complexes are emissive at room temperature in a variety of solvents and at 77 K in butyronitrile glassy matrix, with the long-lived, structured emission appearing between 600 and 750 nm. The emitting states are assigned to predominantly the 3π, π* state with an admixture of 3MLCT characters. Upon ns laser excitation at 355 nm, all complexes display broad, moderately strong transient absorption from the visible to the near-IR region. As a result, RSA is observed from all complexes at 532 nm for ns laser pulses. The strength of the RSA for these complexes follows the trend: Pt-2 > Pt-3 > Pt-4 > Pt-1 >> Pt-5 > Pt-6, which correlates well with the trend of the estimated ΦTσex/σ0 values (where ΦT is the triplet excited state quantum yield, and σex and σ0 are the excited-state and ground-state absorption cross-section, respectively) at 532 nm. It is revealed that substitution at the 7-position of the fluorenyl component exerts a distinct effect on the photophysics and RSA of the complexes. Aromatic substituents such as benzothiazol-2-yl and 2-thionyl cause pronounced red-shifts of the absorption bands, the emission bands, and the transient difference absorption bands, but a decrease of the RSA at 532 nm. Platinum(II) complexes bearing 2-(9,9-dihexadecyl-7-R-fluoren-2-yl)-1,10-phenanthroline ligands exhibit a long-lived, broadband-absorbing excited state and strong reverse saturable absorption (RSA) at 532 nm for ns laser pulses. The substituent at the 7-position of the fluorenyl component exerts a pronounced effect on both the photophysical properties and the RSA. Copyright
- Liu, Xu-Guang,Sun, Wenfang
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supporting information
p. 4732 - 4742
(2013/09/24)
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- Tuning the photophysical properties of N∧N Pt(II) bisacetylide complexes with fluorene moiety and its applications for triplet-triplet- annihilation based upconversion
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Fluorene-containing aryl acetylide ligands were used to prepare N∧N Pt(ii) bisacetylide complexes, where aryl substituents on the fluorene are phenyl (Pt-1), naphthal (Pt-2), anthranyl (Pt-3), pyrenyl (Pt-4), 4-diphenylaminophenyl (Pt-5) and 9,9-di-n-octylfluorene (Pt-6) (where N∧N ligand = 4,4′-di-tert-butyl-2,2′-bipyridine, dbbpy). All the complexes show room temperature (RT) phosphorescence. The emissive T1 excited states of Pt-1, Pt-5 and Pt-6 were assigned as metal-to-ligand-charge- transfer state (3MLCT), whereas for Pt-2, Pt-3 and Pt-4, the emissive T1 excited states were identified as the intraligand state ( 3IL), based on steady state emission spectra, the lifetime of the T1 state, emission spectra at 77 K, spin density analysis and the time-resolved transient absorption spectroscopy. Exceptionally long lived T 1 excited state was observed for Pt-3 (τ = 66.7 μs) and Pt-4 (τ = 54.7 μs), compared to a model complex dbbpy Pt(ii) Bisphenylacetylide (τ = 1.25 μs). RT phosphorescence of anthracene was observed at 780 nm with Pt-3. The critical role of the fluorene is to move the absorption of the complexes to the red-end of the spectra, but at the same time, without compromising the energy level of the T1 state of the complexes. The advantage of this unique spectral tuning effect and the long-lived T1 excited states of Pt-4 was demonstrated by the enhanced performance of the complexes as triplet sensitizers for triplet-triplet annihilation (TTA) based upconversion; an upconversion quantum yield (ΦUC) up to 22.4% was observed with Pt-4 as the sensitizer. Other complexes described herein show negligible upconversion. The high upconversion quantum yield of Pt-4 is attributed to its intense absorption of visible light and long-lived T1 excited state. Based on the result of Pt-4, we propose that weakly phosphorescent, or non-phosphorescent transition metal complexes can be used as triplet sensitizers for TTA upconversion, compared to the phosphorescent triplet sensitizers currently used for TTA upconversion. Our results will be useful for the design of transition metal complexes to enhance the light-absorption and thereafter the cascade photophysical processes, without decreasing the T1 excited state energy levels, which are important for the application of the complexes as triplet sensitizers in various photophysical processes. The Royal Society of Chemistry 2012.
- Li, Qiuting,Guo, Huimin,Ma, Lihua,Wu, Wanhua,Liu, Yifan,Zhao, Jianzhang
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supporting information; experimental part
p. 5319 - 5329
(2012/05/20)
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- Synthesis and photophysics of platinum(II) complexes bearing 2-(7-(4-R-phenylethynyl)-9,9-dihexadecyl-fluoren-2-yl)-1,10-phenanthroline ligand
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A series of platinum(II) complexes bearing 2-(7-(4-R-phenylethynyl)-9,9- dihexadecyl-fluoren-2-yl)-1,10-phenanthroline ligand were synthesized and characterized. Their photophysical properties were systematically investigated by UV-Vis absorption, emission, and transient absorption spectroscopy. All complexes exhibit 1π,π absorption bands below 410 nm and charge transfer transitions at 415-550 nm in CH2Cl2. They all emit at ca. 624 nm with vibronic structures. Both UV-Vis absorption and emission spectra show negative solvatochromic effect. All complexes exhibit broad and moderately strong triplet transient absorption from the near-UV to the near-IR spectral region. Reverse saturable absorption of these complexes in CH 2Cl2 for ns laser pulses at 532 nm was demonstrated.
- Liu, Xu-Guang,Sun, Wenfang
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experimental part
p. 140 - 147
(2012/07/14)
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- Tellurophenes with delocalized π-systems and their extended valence adducts
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The π-conjugated 2,5-substituted tellurophene compounds 2,5-bis(2-(9,9-dihexylfluorene))tellurophene (1) and 2,5-diphenyltellurophene (3) were synthesized through ring closing reactions of 1,4-substituted butadiyne. The oxidative addition of Br2 to tellurophene compounds 1 and 3 was studied through absorption spectroscopy, NMR, electrochemistry, X-ray crystallography, and density functional theory (DFT) calculations. When Br 2 adds to the tellurium center the absorption spectrum shifts to a lower energy. From electrochemistry and DFT calculations we show that this is caused by lowering the lowest unoccupied orbital. The highest occupied orbital is also lowered, but to a lesser extent. This shift in absorption spectrum and lowering of the oxidation potential can provide a method to modify tellurophene containing materials. The two-electron oxidative addition is promising for catalyzing energy storage reactions.
- McCormick, Theresa M.,Jahnke, Ashlee A.,Lough, Alan J.,Seferos, Dwight S.
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experimental part
p. 3542 - 3548
(2012/04/10)
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- One-photon photophysics and two-photon absorption of 4-[9,9-Di(2- ethylhexyl)-7-diphenylaminofluoren-2-yl]-2,2′:6′, 2″-terpyridine and their platinum chloride complexes
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The synthesis, one-photon photophysics and two-photon absorption (2PA) of three dipolar D-π-A 4-[9,9-di(2-ethylhexyl)-7-diphenylaminofluoren-2-yl]-2, 2′:6′,2″-terpyridine and their platinum chloride complexes with different linkers between the donor and acceptor are reported. All ligands exhibit 1π,π* transition in the UV and 1π,π*/1ICT (intramolecular charge transfer) transition in the visible regions, while the complexes display a lower-energy 1π,π*/1CT (charge transfer) transition in the visible region in addition to the high-energy 1π,π* transitions. All ligands and the complexes are emissive at room temperature and 77 K, with the emitting excited state assigned as the mixed 1π, π* and 1CT states at RT. Transient absorption from the ligands and the complexes were observed. 2PA was investigated for all ligands and complexes. The two-photon absorption cross-sections (θ2) of the complexes (600-2000 GM) measured by Z-scan experiment are much larger than those of their corresponding ligands measured by the two-photon induced fluorescence method. The ligand and the complex with the ethynylene linker show much stronger 2PA than those with the vinylene linker.
- Ji, Zhiqiang,Li, Yunjing,Pritchett, Timothy M.,Makarov, Nikolay S.,Haley, Joy E.,Li, Zhongjing,Drobizhev, Mikhail,Rebane, Aleksander,Sun, Wenfang
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scheme or table
p. 2479 - 2491
(2011/04/24)
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- Phenylacetylene dendrimers containing a fluorene core: Synthesis and spectroscopic studies
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Phenylacetylene dendrimers 9-11 containing fluorene as the core with a larger HOMO-LUMO energy gap were synthesized and characterized. Their structure and properties were studied by UV, FL, 1H NMR, MS etc. These novel phenylacetylene dendrimers exhibit unique photophysical properties. They exist a new absorption band around 340 nm whose molar coefficient decreases with increasing generation. The band-gaps of 9-11 are 3.54, 3.43 and 3.02 respectively. The fluorescence quantum yield of 10 is as high as 0.61.
- Wang, Chengyun,Zhong, Hanbin,Li, Shanshan,Shu, Weifu,Shen, Yongjia
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scheme or table
p. 699 - 704
(2010/11/02)
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- Selective fluorescence sensing of zinc and mercury ions with hydrophilic 1,2,3-triazolyl fluorene probes
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The ability to rapidly detect biologically and environmentally significant metal ions such as zinc and mercury is important to study a number of important cellular and environmental processes. Hydrophilic bis(1,2,3-triazolyl)fluorene- based derivatives containing a 1,2,3-triazole-based recognition moiety were synthesized through Click chemistry and characterized by UV-vis absorption, fluorescence emission, and two-photon absorption as new fluorescence sensing probes, selective for Zn2+ and Hg2+ ions. The UV-vis absorption and fluorescence emission spectra of the complexes exhibited blue-shifted absorption and emission spectra upon chelation to Zn2+ and Hg2+ ions, resulting in ca. 2-fold enhancement in fluorescence. Fluorometric titration revealed that 1:2 and 1:3 ligand to metal complexes formed with binding constants of 108 and 1016 for Zn 2+ and Hg2+, respectively. The two-photon absorption cross sections for the probes and probe-metal ion complexes ranged from 200 to 350 GM at 800 nm. These novel fluorescent compounds may have potential as new metal ion sensors to probe cellular and biological environments.
- Nguyen, Dao M.,Frazer, Andrew,Rodriguez, Luis,Belfield, Kevin D.
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scheme or table
p. 3472 - 3481
(2011/12/03)
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- Practical electrochemical iodination of aromatic compounds
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A practical method for electrochemical iodination of aromatic compounds was developed. The method involves the generation of I+ by electrochemical oxidation of I2 in CH3CN using H 2SO4 as supporting electrolyte followed by the reaction with aromatic compounds. The para/ortho selectivity for the reaction of mono-substituted benzenes was significantly improved using dimethoxyethane as cosolvent in the second step. The reaction with highly reactive aromatic compounds led to the formation of significant amounts of diiodo compounds in a macrobatch reactor. This problem was solved by fast 1:1 mixing of I+ with an aromatic compound using a microflow system consisting of a T-shaped micromixer and a microtube reactor.
- Kataoka, Kazuhide,Hagiwara, Yuji,Midorikawa, Koji,Suga, Seiji,Yoshida, Jun-Ichi
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p. 1130 - 1136
(2013/01/03)
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- DYE-SENSITIZED PHOTOELECTRIC CONVERSION DEVICE
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Disclosed is a photoelectric conversion device wherein a methine dye represented by the formula (1) below is supported by a thin film of oxide semiconductor particles arranged on a substrate. Also disclosed is a solar cell manufactured by using such a photoelectric conversion device. (In the formula (1), n represents an integer of 0-5; m represents an integer of 0-5; R1-R4 independently represent a hydrogen atom, an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; X and Y independently represent a hydrogen atom; an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; Z represents an oxygen atom, a sulfur atom or the like; A1, A2, A3, A4 and A5 independently represent a hydrogen atom, an optionally substituted aromatic residue, an optionally substituted aliphatic hydrocarbon residue or the like; and rings a, b and c may be substituted.)
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Page/Page column 51
(2008/12/08)
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- PROCESS FOR PRODUCING AROMATIC IODINE COMPOUND
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A process for producing an aromatic iodine compound. It has advantages of ease of handling and high safety. By the process, the reaction product having an excellent colour tone can be produced in a high yield. The process for aromatic iodine compound production is characterized by introducing an aromatic compound and an active iodizing agent into a flow-through type reactor equipped with a high-speed mixer to continuously replace hydrogen atoms of the aromatic nucleus of the aromatic compound with iodine atoms.
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- Synthesis of a fluorescent PNA monomer containing 5-((9H-fluoren-2-yl) ethynyl)uracil
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Pyrimidine nucleobases bearing 5-phenylethynyl substitution represent compact and intrinsically fluorescent nucleobases. Such nucleobases are capable of selective recognition of a complementary base and may fluorimetrically report on hybridization events. Our past work has demonstrated that the fluorescence of 5-phenylethynyluracils is sensitive to substitution on the phenyl ring, however these are relatively weak fluorophores. We currently are pursuing the functionalization of the phenyl group of these modified nucleobases in order to further improve their fluorescence response, increase their aqueous solubility and stabilize hybrids formed with complementary nucleic acids. As an example of this work, we have synthesized the 5-((9 H-fluoren-2-yl)ethynyl)uracil PNA monomer that will be incorporated into oligomers using Fmoc-based chemistry. Initial evaluation of the fluorescence of the 5-((9 H-fluoren-2-yl)ethynyl) uracil derivative shows that the fluorescence intensity is approximately 50 times greater than a similar 5-phenylethynyluracil derivative when under identical conditions. Copyright Taylor & Francis Group, LLC.
- Wojciechowski, Filip,Hudson, Robert H. E.
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p. 1199 - 1202
(2008/09/17)
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- PROCESS FOR PRODUCING AROMATIC IODINE COMPOUND
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A process for producing an aromatic iodine compound. It has advantages of ease of handling and high safety. By the process, the reaction product having an excellent color tone can be produced in a high yield. The process for aromatic iodine compound production is characterized by introducing an aromatic compound and an active iodizing agent into a flow-through type reactor equipped with a high-speed mixer to continuously replace hydrogen atoms of the aromatic nucleus of the aromatic compound with iodine atoms.
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Page/Page column 18-19; 24-25
(2008/06/13)
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- Solid-phase iodination of arenes with the system iodine-diacetoxy(phenyl)- λ3-iodane
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The system iodine-diacetoxy(phenyl)-λ3-iodane in the solid phase is capable of iodinating activated arenes.
- Krasnokutskaya,Trusova,Filimonov
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p. 1750 - 1751
(2007/10/03)
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- Process for producing iodinated aromatic compounds
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Disclosed is a process for producing an iodinated aromatic compound, which comprises reacting an aromatic compound with an iodine compound in the presence of a chlorate as an oxidizing agent.
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- Alkynic compounds, their use as monomers in vacuum deposition polymerisation, thin films formed from these polymers and their use in electroluminescent devices
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The present invention relates to an organic compound having acetylene group(s), a thin film formed by vacuum deposition polymerization using said organic compound, vacuum deposition polymerization to form said thin film, and an electroluminescence device containing said thin film. More particularly, the present invention relates to an organic compound having at least one acetylene groups, vacuum deposition polymerization in which said organic compound is deposited on the substrate and simultaneously or then polymerized by heat treatment or UV irradiation to form a polymer thin film. and an electroluminescence device using at least one layer of said thin film.
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- Iodination and chlorination of aromatic polycyclic hydrocarbons with iodine monochloride in aqueous sulfuric acid
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Polycyclic aromatic hydrocarbons when treated with iodine monochloride in water solutions of sulfuric acid afford iodo-and chloroderivatives. Biphenyl, fluorene, acenaphthene, 1-nitronaphthalene undergo iodination. Naphthalene furnishes a mixture of iodo-and chloroderivatives, prevailing the latter. Anthracene and phenanthrene provide only chlorinated products. The iodine monochloride in the sulfuric acid is a stronger iodinating agent than in acetonitrile.
- Chaikovskii,Filimonov
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p. 1130 - 1133
(2007/10/03)
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- Synthesis and Characterization of Oligo(9,9-dihexyl-2,7-fluorene ethynylene)s: For Application as Blue Light-Emitting Diode
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(Formula Presented) Highly soluble and strongly blue fluorescent oligo(9,9-dihexyl-2,7-fluorene ethynylene)s (OFEs) were synthesized by a Pd/Cu-catalyzed Sonogashira coupling reaction. An organic light-emitting diode using pentamer 15 as the emitting material was successfully fabricated and emitted a bright blue light.
- Lee, Sang Ho,Nakamura, Toshikazu,Tsutsui, Tetsuo
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p. 2005 - 2007
(2007/10/03)
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- The Synthesis of Bridged Oligophenylenes from Fluorene 1. Terphenyls and Quaterphenyls
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Improved methods are presented for the alkylation of fluorene (2) to 9,9- dialkylfluorenes (3-6) free from 9-monoalkylfluorenes.Mono- and dihalogenated derivatives of 2-6 are reported as are a variety of ring substituted 9,9-dialkylfluorenes.Halogenated 9,9-dialkylfluorenes and aryl or methyl Grignard reagents were cross-coupled in Pd-catalyzed reactions to generate a series of novel p-oligophenylenes (four terphenyls (26, 27, 29 and 31c) and nineteen quterphenyls (33-6, 64-71 and 73-79)) each possessing one or two dialkylated methylene bridges between aromatic rings.Each bridged oligophneylene showed enhanced solubility, high quantum efficiency and photochemical stability.A number of quaterphenyls incorporated substituents which extended the conjugation of the oligophenylene chromophore.
- Kelley, Charles J.,Ghiorghis, Alem,Kauffman, Joel M.
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p. 2701 - 2733
(2007/10/03)
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- The Decomposition of Arenediazonium Tetrafluoroborates with Halo- and Azidotrimethylsilanes in Nonaqueous Solvents
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The reaction of arenediazonium tetrafluoroborates with chlorotrimethylsilane in a tetrahydrofuran/N,N-dimethylformamide (DMF) (5v/3v) solution afforded the protodediazotization products in high yields.The reactions of the diazonium salts with halotrimethylsilanes in DMF were found to give the corresponding haloarenes.Among the halodediazotization reactions, the iododediazotization with iodotrimethylsilane proceeded smoothly at room temperature to give the iodoarenes in excellent yields.In a similar manner, a variety of azidoarenes were obtained in cosistently high yields by the treatment of arenediazonium tetrafluoroborates with azidotrimethylsilane in a DMF solution.
- Keumi, Takashi,Umeda, Toshiaki,Inoue, Yoshinori,Kitajima, Hidehiko
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- Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
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The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 439 - 443
(2007/10/02)
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