- Solvent-free luminescent organic liquids
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Illuminating! Isolation of a π-core by covalently attached flexible hydrocarbon chains has been employed to synthesize blue-emitting oligo(p-phenylenevinylene) (OPV) liquids with tunable viscosity and optical properties. A solvent-free, stable, white-light emitting ink/paint, which can be applied onto various surfaces and even onto LEDs, was made by blending of liquid OPVs with emissive solid dopants. Copyright
- Santhosh Babu, Sukumaran,Aimi, Junko,Ozawa, Hiroaki,Shirahata, Naoto,Saeki, Akinori,Seki, Shu,Ajayaghosh, Ayyappanpillai,Moehwald, Helmuth,Nakanishi, Takashi
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Read Online
- Organic fluorescent molecule with high solid state luminescent efficiency and protonation stimuli-response
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A novel organic fluorophor with high solid state luminescent efficiency based on 1,4-bis(2,2-di(pyridin-2-yl)vinyl)benzene (BDP2VB) was designed and synthesized. It emits faintly in solution, but becomes a strong emitter in the aggregate state, demonstrating its aggregation induced emission (AIE) property. According to the crystal structure analysis, J-type aggregation was formed in the packing mode of the molecule, which was demonstrated to be beneficial to gain high fluorescent quantum efficiency in solid state. Additionally, the emission color of BDP2VB can change dramatically in solid state as well as in solution by the protonation stimuli. Copyright
- Ma, Suqian,Zhang, Jibo,Chen, Jinlong,Wang, Lijuan,Xu, Bin,Tian, Wenjing
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Read Online
- Rational self-assembly of polygonal organic microcrystals for shape-dependent multi-directional 2D optical waveguides
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Micro-nano-level photonic waveguide regulation is essential for future on-chip photonic integrated systems and is still of great challenges. We report a molecular design strategy, changing the position of the methyl substituent makes the arrangement of the three isomer molecules different in their respective crystals. Based on this strategy, three sheet-like crystals with different polygonal morphologies were prepared via solution self-assembly approach. The in-depth optical measurements demonstrated that these three microsheet crystals have different 2D optical waveguide performances related to the shapes. Our work provides a feasible design strategy and material preparation method for realizing precise 2D optical waveguide modulation, which lays the foundation for complex photonic integrated systems in the future.
- Liao, Liang-Sheng,Lv, Qiang,Wang, Xue-Dong,Xu, Chao-Fei,Yan, Chang-Cun,Yu, Yue
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supporting information
(2021/12/29)
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- Selective esterification of phosphonic acids
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Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.
- Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
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- Linear and Star-Shaped Extended Di- and Tristyrylbenzenes: Synthesis, Characterization and Optical Response to Acid and Metal Ions
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Two linear 1,4-distyrylbenzenes and five star-shaped 1,3,5-tristyrylbenzene derivatives (L2a and L2b, Y0–Y3 and YNBu) were synthesized and spectroscopically characterized. The photophysical properties, optical response to acid and metal ions were investigated. Upon backbone extension of linear distyrylbenzenes or the introduction of dibutylanilines, the electronic spectra are redshifted. Incorporation of electron-deficient pyridyl units does not significantly affect the optical properties. Variation of the number of pyridine rings and substitution pattern tune the fluorescence response to acids and metal ions. The novel arenes discriminate Al3+, Mn2+, Fe3+, Fe2+, Cd2+, Ag+ and Hg2+.
- Bunz, Uwe H. F.,Freudenberg, Jan,Kotlear, Eugen A.,Kushida, Soh,Maier, Steffen,Rominger, Frank,Zhang, Hao
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- Piezochromic Luminescence of Donor–Acceptor Cocrystals: Distinct Responses to Anisotropic Grinding and Isotropic Compression
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Piezochromic luminescent materials that exhibit distinct luminescence responses to different types of mechanical stresses have been emerging as new kinds of materials which are rarely investigated. Herein, we report a donor–acceptor (D–A) charge-transfer (CT) cocrystal, which shows distinct hypochromatic and bathochromatic shifts upon anisotropic grinding and isotropic compression, respectively. Detailed spectroscopic and structural analyses revealed that the hypochromatic shifted emission under grinding is attributable to a structural reorganization from a loosely segregated-stack to a mixed-stack, while the bathochromatic shifted emission originates from the formation of a tighter packing structure. We present rare evidence of a distinct luminescent response to anisotropic grinding and isotropic compression on the basis of structural rearrangement in a D–A cocrystal, and thus enriches our insight into piezochromic luminescence.
- Liu, Yingjie,Zeng, Qingxin,Zou, Bo,Liu, Yu,Xu, Bin,Tian, Wenjing
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supporting information
p. 15670 - 15674
(2018/11/23)
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- Distyrylbenzene-based segmented conjugated polymers: Synthesis, thin film morphology and chemosensing of hydrophobic and hydrophilic nitroaromatics in aqueous media
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Two new segmented conjugated polymers bearing distyrylbenzene chromophoric units and their model compounds were synthesized. The tendency of the model compounds to form H- and J-type aggregates in the amorphous matrix was greatly diminished by the twisted polymeric architecture. Fluorescence anisotropy measurements indicated good exciton mobilities in condensed phase. Fluorescence quenching by nitroaromatic aqueous solutions was fast, complete, selective and reversible pointing to a rapid diffusion of analytes into the films. The quenching response to nitrophenols was superior to that against nitrotoluenes. The increase of the electron-donating capabilities by diethoxy-substitution was detrimental to the amorphous morphology and it did not increase sensitivity to NACs. Quenching efficiencies of polymers were not modified when MeOH was used instead of water. The solubility parameter distances, Ra. indicate that the sensing materials show higher responses when their affinity with the analytes is lower. This observation could help in the designing of fluorescent sensors.
- Almassio, Marcela F.,Romagnoli, Maria J.,Del Rosso, Pablo G.,Schvval, Ana Belén,Garay, Raúl O.
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p. 167 - 179
(2017/03/02)
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- Hydrophilic Conjugated Polymers Prepared by Aqueous Horner-Wadsworth-Emmons Coupling
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The synthesis of hydrophilic conjugated polymers typically relies on organometallic coupling methodologies. Here we present an approach to prepare polar poly(arylene-vinylene)s (PAVs) in water using the Horner-Wadsworth-Emmons (HWE) reaction. The additional preparation of discrete arylene vinylene (AVs) afforded insight into HWE kinetics and regioselectivity. Nine novel PAVs and AVs were synthesized, characterized by UV-vis absorption and ultraviolet photoelectron spectroscopy, and studied for their utility in sensing and photovoltaic applications.
- Page, Zachariah A.,Liu, Yao,Puodziukynaite, Egle,Russell, Thomas P.,Emrick, Todd
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p. 2526 - 2532
(2016/05/19)
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- Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds
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Detection of cerebral β-amyloid (Aβ) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential Aβ imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower Log?P values, and studied their fluorescent properties and Aβ binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for Aβ plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a Log?P value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl)benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents.
- Nabuurs, Rob J.A.,Kapoerchan, Varsha V.,Metaxas, Athanasios,Hafith, Sarah,de Backer, Maaike,Welling, Mick M.,Jiskoot, Wim,van den Nieuwendijk, Adrianus M.C.H.,Windhorst, Albert D.,Overkleeft, Herman S.,van Buchem, Mark A.,Overhand, Mark,van der Weerd, Louise
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p. 6139 - 6148
(2016/11/30)
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- Design of Assembled Systems Based on Conjugated Polyphenylene Derivatives and Carbon Nanohorns
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Promising materials have been designed and fully characterised by an effective interaction between versatile platforms such as carbon nanohorns (CNHs) and conjugated molecules based on thiophene derivatives. Easy and non-aggressive methods have been described for the synthesis and purification of the final systems. Oligothiophenephenylvinylene (OTP) systems with different geometries and electron density are coupled to the CNHs. A wide range of characterization techniques have been used to confirm the effective interaction between the donor (OTP) and the acceptor (CNH) systems. These hybrid materials show potential for integration into solar cell devices. Importantly, surface-enhanced Raman spectroscopy (SERS) effects are observed without the presence of any metal surface in the system. Theoretical calculations have been performed to study the optimised geometries of the noncovalent interaction between the surface and the organic molecule. The calculations allow information on the monoelectronic energies of HOMO–LUMO orbitals and band gap of different donor systems to be extracted.
- Iglesias, Daniel,Guerra, Javier,Gómez, M. Victoria,Rodríguez, Antonio M.,Prieto, Pilar,Vázquez, Ester,Herrero, M. Antonia
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p. 11643 - 11651
(2016/08/05)
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- NOVEL LIQUID CRYSTALLINE COMPOUND, LIQUID CRYSTAL COMPOSITION, OPTICAL ELEMENT AND OPTICAL DISPLAY DEVICE
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PROBLEM TO BE SOLVED: To provide a novel liquid crystalline compound that is low in dielectric anisotropy, has responsiveness, and changes its birefringence by application of voltage. SOLUTION: The present invention provides a compound represented by formula (1) (In the formula (1), R1, R2 and R3 independently represent a hydrogen atom or C1-C10 alkyl, in the alkyl, at least one -CH2- may be substituted by -O-, -S-, -CO-, or -SiH2-, and at least one -(CH2)2- may be substituted by -CH=CH-or -C≡C-. n is an integer of 0-4. m is an integer of 1 or 2. Z1 and Z2 are -CH=CH-). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0081
(2018/10/16)
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- Liquid-crystal styrylacrylic deriv., its manufacturing method, and conductive liquid crystal material excellent solubility in organic semiconductor element
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PROBLEM TO BE SOLVED: To provide a liquid crystalline styryl derivative having an excellent electroconductivity and excellent solubility in organic solvents such as hexane, and a method for producing the same, an electroconductive liquid crystalline material using the liquid crystalline styryl derivative and an organic semiconductor element.SOLUTION: This liquid crystalline styryl derivative is characterized by being shown by general formula (1). (In the formula, Rrepresents an alkyl group, and n denotes an integer of 0-2). Furthermore, n in formula (1) denoting 1-2 and Rrepresenting a 4-18C alkyl group are especially preferable.
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Paragraph 0085
(2018/10/10)
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- Molecular structures of the products of a diphosphonate ester building block with lewis bases
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By treating a suitable Wittig reagent under acid conditions, the phosphonate ester 1,4-bimethylenebenzene phosphonate ethyl ester (H2[BBPE], 1) was obtained. As a building block, compound 1 has been reacted with the Lewis-base N,N-dimethylpiperazine, ammonia and NaOH yielded compounds 2-4. The crystal structures show that a 1D chain forming a tubular channel is constructed through hydrogen bonds in 1; hydrogen bonds form two 1D chains with left-hand and right-hand helixes and form 3D networks in compound 2; 1D hydrogen-bond chains are further connected together to afford a 3D network architecture in compound 3; the phosphonate is coordinated by two Na atoms which present different coordination environments in compound 4. Additionally, the relationships between the structure and fluorescence of the four compounds in the solid state and in different solvents have also been studied at room temperature.
- Li, Yufeng,Jian, Fangfang
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p. 14435 - 14450
(2015/09/22)
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- Design and self-assembly of variform organometallic macrocycle with terminal imidazole-based bridging ligands utilizing joints twist and rotation
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Organometallic macrocycles based on bridge ligands with terminal imidazole groups show the formation of various patterns. The end imidazolyl finishes the conjugated system on the back bone and can freely twist or rotate just like the joints of a human body such as the knee and wrist.
- Wu, Tong,Lin, Yue-Jian,Jin, Guo-Xin
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supporting information
p. 2356 - 2360
(2014/02/14)
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- Tailor-made highly luminescent and ambipolar transporting organic mixed stacked charge-transfer crystals: An isometric donor-acceptor approach
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We have rationally designed a densely packed 1:1 donor-acceptor (D-A) cocrystal system comprising two isometric distyrylbenzene- and dicyanodistyrylbenzene-based molecules, forming regular one-dimensional mixed stacks. The crystal exhibits strongly red-shifted, bright photoluminescence originating from an intermolecular charge-transfer state. The peculiar electronic situation gives rise to high and ambipolar p-/n-type field-effect mobility up to 6.7 × 10-3 and 6.7 × 10-2 cm2 V-1 s-1, respectively, as observed in single-crystalline OFETs prepared via solvent vapor annealing process. The unique combination of favorable electric and optical properties arising from an appropriate design concept of isometric D-A cocrystal has been demonstrated as a promising candidate for next generation (opto-)electronic materials.
- Park, Sang Kyu,Varghese, Shinto,Kim, Jong H.,Yoon, Seong-Jun,Kwon, Oh Kyu,An, Byeong-Kwan,Gierschner, Johannes,Park, Soo Young
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supporting information
p. 4757 - 4764
(2013/05/08)
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- IMAGING LIGANDS
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Compound or a salt or solvate thereof for use as an imaging ligand for the detection of aggregated amyloid-β or for use as a medicament according to the formula (I): wherein R1 and R3 may be the same or different optionally substituted pyridinyl group and wherein R2 is hydrogen or a substituent group comprising at least an oxygen atom or a fluor atom.
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Page/Page column 7
(2013/05/22)
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- Molecular docking studies of (1E,3E,5E )-1,6-bis(substituted phenyl)-hexa-1,3,5-triene and 1,4-bis(substituted trans-styryl)benzene analogs as novel tyrosinase inhibitors
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We simulated the docking of the tertiary structure of mushroom tyrosinase with our compounds. From the structure-tyrosinase inhibitory activity relationship, it is notable that compounds 4, 8 and 11 showed similar or better activity rates than kojic acid which was used as a positive control. Compounds 17, 21, and 23 among benzene analogs that possess the same substituent showed significantly lower tyrosinase inhibitory effects. Therefore, we have confirmed that among the compounds showing better tyrosinase inhibitory effects than kojic acid, the compounds with triene analogs have better tyrosinase inhibitory effect than the compounds with benzene analogs. Docking simulation suggested the mechanism of compounds by several key residues which had possible hydrogen bonding interactions. The pharmacophore model underlined the features of active compounds, 4,4′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)diphenol, 5,5′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxy-phenol), and 5,5′-((1 E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol among triene derivatives which had several hydrogen bond groups on both terminal rings. The soundness of the docking results and the agreement with the pharmacophores suggest that it can be conveniently exploited to design inhibitors with an improved affinity for tyrosinase.
- Ha, Young Mi,Lee, Hye Jin,Park, Daeui,Jeong, Hyoung Oh,Park, Ji Young,Park, Yun Jung,Lee, Kyung Jin,Lee, Ji Yeon,Moon, Hyung Ryong,Chung, Hae Young
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- Aggregation induced emission (AIE) of trifluoromethyl substituted distyrylbenzenes
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The AIE properties of two trifluoromethyl substituted distyrylbenzene model compounds were compared. The fluorescence quantum efficiency of these molecules can be modulated by tuning their subtle solid-state intermolecular interactions.
- Shi, Zhengwei,Davies, Joshua,Jang, Sei-Hum,Kaminsky, Werner,Jen, Alex K.-Y.
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supporting information; experimental part
p. 7880 - 7882
(2012/08/28)
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- Synthesis and photophysical studies of back-to-back dinuclear platinum terpyridine complexes with different substituents on the bridging ligand
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Four back-to-back dinuclear platinum terpyridine complexes with different substituents on the bridging ligand (1a-1d) were synthesized and characterized. Their electronic absorption, photoluminescence and triplet transient difference absorption were systematically investigated. All complexes exhibit strong 1MLCT/1ILCT absorption bands in the visible region, which significantly red-shifts when electron-donating substituents are introduced on the conjugated bridge and blue-shifts when electron-withdrawing substituents are present. Excitation of 1a and 1d in solution at their respective low-energy absorption band at room temperature results in an orange and red luminescence, respectively, which can be tentatively attributed to the 1MLCT/ 1ILCT excited state. These complexes exhibit intense broad triplet transient difference absorption in the visible to the near-IR region, which likely arises from the ligand-localized states (3π,π* or 3ILCT). Electron-donating substituent causes a pronounced red-shift, while electron-withdrawing substituents induce a blue-shift of the triplet transient absorption bands.
- Liu, Rui,Li, Zhongjing,Zhu, Hongjun,Sun, Wenfang
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scheme or table
p. 383 - 389
(2012/07/14)
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- Organic-inorganic hybrid porous sulfonated zinc phosphonate material: Efficient catalyst for biodiesel synthesis at room temperature
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A new porous zinc phosphonate material (HZnP-1) has been synthesized via the reaction between p-xylenediphosphonic acid and anhydrous ZnCl2 under hydrothermal and mildly acidic conditions (pH ～ 5) in the absence of any structure directing agent. The phenyl group of this material has been sulfonated with concentrated sulfuric acid to obtain sulfonic acid functionalized material HZnPS-1. Powder X-ray diffraction (XRD), field emission scanning electron microscopy (FE SEM), N2 sorption, solid state 13C CP MAS and 31P MAS NMR, and FT IR spectroscopic tools are employed to characterize these materials. The crystal structures of both the materials are indexed corresponding to the new orthorhombic phases with unit cell parameters a = 11.00, b = 8.74, c = 14.62 A, α = β = γ = 90° for HZnP-1, and a = 10.65, b = 13.52, c = 15.30 A and α = β = γ = 90° for HZnPS-1. HZnPS-1 showed outstanding catalytic activity and high recycling efficiency for the synthesis of different biodiesel compounds via esterification of long chain fatty acids by using methanol as both reactant and solvent at room temperature. The green and eco-friendly catalytic system described herein can overcome the problem faced by the existing catalytic systems known in biodiesel synthesis, such as drastic conditions (high reaction temperature) and requirement of hazardous organic solvents.
- Pramanik, Malay,Nandi, Mahasweta,Uyama, Hiroshi,Bhaumik, Asim
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experimental part
p. 2273 - 2281
(2012/09/08)
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- Gold(I) styrylbenzene, distyrylbenzene, and distyrylnaphthalene complexes: High emission quantum yields at room temperature
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One gold(I)-substituted styrylbenzene, six digold(I) distyrylbenzenes, one tetragold distyrylbenzene, and four digold distyrylnaphthalene complexes were synthesized using base-promoted auration, alkynylation, triazolate formation, and Horner-Wadsworth-Emmons reactions. The gold(I) fragments are either σ-bonded to the aromatic system, or they are attached through an alkynyl or triazolate spacer. Product formation was monitored using 31P{ 1H} NMR spectroscopy. Systems in which gold(I) binds to the central benzene ring or the terminal phenyl rings were designed. All of these complexes have strong ultraviolet absorptions and emit blue light. The position of the gold(I) attachment influences the luminescence efficiency. Complexes with two gold(I) fragments attached to the ends of the conjugated system have fluorescence quantum yields up to 0.94, when using 7-diethylamino-4- methylcoumarin as the emission standard. Density-functional theory calculations on three high-yielding emitters suggest that luminescence originates from the distyrylbenzene or -naphthalene bridge. Copyright
- Gao, Lei,Niedzwiecki, Daniel S.,Deligonul, Nihal,Zeller, Matthias,Hunter, Allen D.,Gray, Thomas G.
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scheme or table
p. 6316 - 6327
(2012/06/30)
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- The synthesis and photophysical properties of novel poly(diarylamino) styrenes
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A series of novel diamines linked by varying conjugated bridges were characterized using FTIR, NMR and UV-visible spectroscopy, mass spectrometry and elemental analysis. The photoluminescence and thermal properties of the compounds were related to structure and quantum chemical calculations were employed to study the optimized ground state geometry of the compounds. The diarylamines exhibited blue to green fluorescence emission and displayed high thermal stability and high glass transition temperature. As such, the compounds might be very useful as hole-transporting materials in organic light-emitting diodes.
- Wang, Hai-Ying,Chen, Gang,Xu, Xiao-Ping,Chen, Hua,Ji, Shun-Jun
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experimental part
p. 358 - 365
(2011/06/11)
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- Phenolic bis-styrylbenzenes as β-amyloid binding ligands and free radical scavengers
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Starting from bisphenolic bis-styrylbenzene DF-9 (4), β-amyloid (Aβ) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with β-amyloid peptide Aβ1-40 and a fluorescence assay using APP/PS1 transgenic mouse brain sections. Bis-styrylbenzene SAR is derived largely from work on symmetrical compounds. This study is the first to describe Aβ binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an Aβ binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood-brain barrier and bound to Aβ plaques in vivo. By use of a DPPH assay, phenol functional groups with para orientations seem to be a necessary, but insufficient, criterion for good free radical scavenging properties in these compounds.
- Flaherty, Daniel P.,Kiyota, Tomomi,Dong, Yuxiang,Ikezu, Tsuneya,Vennerstrom, Jonathan L.
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scheme or table
p. 7992 - 7999
(2011/03/19)
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- H-shaped OPE/OPV oligomers: A new member of 2D-conjugated fluorophore cores
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(Chemical Equation Presented) A new class of two-dimensional (2D), π-conjugated, skewed H-shaped co-oligomers of phenylene vinylene and phenylene ethynylene (11a-d, termed H-mers) were synthesized using Sonogashira coupling and Wittig-Horner reactions as the key steps. Electronic and spectroscopic properties of the H-mers were investigated by UV-vis absorption, fluorescence spectroscopic techniques, and ab initio calculations (HF/3-21G). Two amino-containing functional H-mers (11b and 11d) were found to exhibit appealing fluorescence sensitivity to selected Bronsted acids and transition-metal ions.
- Zhou, Ningzhang,Wang, Li,Thompson, David W.,Zhao, Yuming
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supporting information; experimental part
p. 3001 - 3004
(2009/04/18)
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- Luminescent amphiphilic dendrimers with oligo(p-phenylene vinylene) core branches and oligo(ethylene oxide) terminal chains: Syntheses and stimuli-responsive properties
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A class of new dendrimers consisting of hydrophobic oligo(p-phenylene vinylene) core branches and hydrophilic oligo(ethylene oxide) terminal chains was synthesized. These amphiphilic dendritic molecules are highly luminescent and exhibit critical micellization behaviors. They also show a lower critical solution temperature (LCST) in an aqueous medium. Both the critical micelle concentration (CMC) and LCST increased with increasing branch number and the ratio of the hydrophilic oligo(ethylene oxide) to hydrophobic oligo(p-phenylene vinylene) moieties. Besides, a temperature-dependent phase transition from a clear to cloudy aqueous solution was observed. The temperature-induced phase transition was also reflected by fluorescence quenching, 1H NMR resonance peak broadening, and UV-vis absorption shift arising from the hydrophobic conjugated core. These changes in the phase structure and photophysical properties were demonstrated to be highly reversible, indicating some interesting stimuli-responsive behaviors. The Royal Society of Chemistry.
- Chang, Dong Wook,Dai, Liming
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p. 364 - 371
(2008/02/03)
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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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- Electroluminescent properties of heterocyclic conjugated random copolymers containing phenothiazine and carbazole moieties
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Electroluminescent properties of polymer light-emitting diode (PLED)s fabricated from heterocyclic conjugated random copolymers, poly(PZV-ran-CZV), containing (N-2-ethylhexyl)-3,6-phenothiazinylene vinylene (PZV), (N-2-ethylhexyl)-3,6-carbazolylene vinylene (CZV) and phenylene vinylene (PV) unit as a light emitting layer were investigated. PLEDs made with corresponding alternating copolymers, poly(PZV-PV) and poly(CZV-PV), as a light emitting layer were also studied and exhibited EL maximum at 570 nm and 500 nm, respectively. Single-layered PLEDs made with poly(PZV-ran-CZV) copolymers, however, showed EL maxima shifted to longer wavelength. Double-layered PLED made with poly(PZV-ran-CZV) copolymer as a light emitting layer and Alq3 as an electron transporting layer exhibited enhanced EL emission compared to that of single-layered PLED.
- Han, Yoon Soo,Kim, Hoyoung,Jin Seo, Hyeon,Kwon, Younghwan,Hur, Youngjune,Kim, Dong-Uk,Kim, Jung Moo,Kim, Hyun Suk,Park, Lee Soon
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p. 129/[409]-140/[420]
(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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(2008/06/13)
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- STILBENE DERIVATIVE, METHOD FOR PRODUCING THE SAME, AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR
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PROBLEM TO BE SOLVED: To provide a stilbene derivative having bulky groups in the molecule and having specified drum sensitivity characteristics, to provide a method for producing the same, and to provide an electrophotographic photoreceptor containing the same. SOLUTION: The stilbene derivative is represented by formula (1) (wherein the two R1 groups, which are independent of each other, are 6 to 20C substituted or unsubstituted alkyl groups, 6 to 20C substituted or unsubstituted alkoxyl groups, 15 to 20C substituted or unsubstituted aryl groups, or substituted or unsubstituted amino groups). The method for producing the same and the electrophotographic photoreceptor are also provided. The method comprises reacting a specified formylated triphenylamine derivative with a specified diphosphoric acid ester derivative in the presence of a base.
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(2010/02/11)
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- STILBENE DERIVATIVE, METHOD FOR PRODUCING THE SAME, AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR
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PROBLEM TO BE SOLVED: To provide a stilbene derivative having predetermined substituents in the intramolecular triphenylamine structure, thus improved in compatibility with binder resin and yielding predetermined drum sensitivity properties, to provide a method for producing the stilbene derivative, and to provide an electrophotographic photoreceptor containing the stilbene derivative. SOLUTION: The stilbene derivative is represented by general formula(1) ( wherein, A is a bivalent organic group containing a substituted or nonsubstituted aromatic ring; and R1 to R18 are each H, a substituted or nonsubstituted 1-6C alkyl or the like, wherein at least two of R1 to R18 may be bound to or condensed with each other to form a carbocyclic group or heterocyclic group ). The method for producing the stilbene derivative comprises carrying out a reaction between a specific formylated triphenylamine derivative and a specific diphosphoric ester derivative in the presence of a base. The electrophotographic photoreceptor containing the stilbene derivative is also provided.
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Page/Page column 37
(2010/02/13)
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- Hybrid cyclic dimers of divacant heteropolyanions: Synthesis, mass spectrometry (MALDI-TOF and ESI-MS) and NMR multinuclear characterisation
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In the field of organic-inorganic hybrid composites, functionalized polyoxometalates constitute a special class of inorganic nanobuilding blocks (NBBs). This study represents a first approach related to the formation of new oligomeric hybrid species based on the reaction of bis(electrophilic) groups with a divacant heteropolyanion as the NBB. Bis(phosphonates) such as para-H2O3PCH2(C6H4) nCH2PO3H2 (n = 1 or 2) have been treated with the divacant heteropolyanion [γ-SiW10O 36]8- to form the hybrid cyclic dimer [H 2((SiW10O36) (O=PCH2(C 6H4)nCH2P=O)]2] 6-. MALDI-TOF and ESI mass spectrometry have been used as essential analytical techniques for the characterization of such composite systems. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Mayer, Cedric R.,Herve, Maryline,Lavanant, Helene,Blais, Jean-Claude,Secheresse, Francis
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p. 973 - 977
(2007/10/03)
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- Polyaromatic amines. Part 3: Synthesis of poly(diarylamino)styrenes and related compounds
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The title compounds were synthesised and characterised as part of a study into new aromatic amines for charge transporting materials. Compounds 12-16, 20-24 and 27-34 are alkene linked triarylamines, compounds 35-36 are hydrazone derivatives and compounds 38-41 are pyrrole substituted triarylamines. Each compound was characterised by cyclic voltammetry.
- Plater, M. John,Jackson, Toby
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p. 4673 - 4685
(2007/10/03)
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- Diarylamino groups as photostable auxofluors in 2-benzoxazolylfluorene, 2,5-diphenyloxazoles, 1,3,5-hexatrienes, 1,4-distyrylbenzenes, and 2,7-distyrylfluorenes
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The relationship of structure to optical spectral properties was determined for five types of fluors in a search for an optimum-wavelength shifter to be used as part of the detection systems for high-energy particles from accelerators. In a search for photostable fluors to serve as waveshifters in plastic fibers it was found that the wavelengths of interest, absorption max 410 ± 10 nm and fluorescence emission max 480 ± 20 nm, along with other properties, such as high solubility and short fluorescence decay time, could be obtained from fluorophors composed of aromatic rings and vinyl groups only by using amino groups as auxochromes to give bathochromic shifts of wavelengths. Since primary, monoalkyl, and dialkylamino groups were not sufficiently photostable, a number of fluorophores bearing diarylamino groups were investigated. Syntheses of the fluors made use of the Buchwald amination, an improved version of the Emmons-Horner reaction, and other common reactions. The fluor types were the following: a 2-benzoxazolyl-7-(4-diarylamino)fluorene 7, 2-(4-cyanophenyl)-5-(4-aminophenyl)oxazoles 14 and 20, 1,3,5-hexatrienes 24a-d and 26a-c, 1,4-distyrylbenzenes 31d-g and 32a-e, and 2,7-distyrylfluorenes 40a,d-e. The unsymmetrical fluors 7, 14, and 20 were not as bright as the best hexatrienes, distyrylbenzenes, and distyrylfluorenes, which were all symmetrical. Where the 1,6-diaryl-1,3,5-hexatrienes 24a-d had high fluorescence quantum yield (Φf), the 1,1,6,6-tetraryl-1,3,5-hexatrienes 26a-c had both lower ε and Φf. Where the 1,4-distyrylbenzenes 31d-g had high Φf, the 1,4-bis(2-phenylstyryl)benzenes 32a-e had (Φf = 0. Diarylamino groups as auxofluors conferred higher photochemical stability than dialkylamino groups on similar fluorophores. The 1,4-distyrylbenzenes 31d,e and the 2,7-distyrylfluorenes 40d,e had the most desirable properties overall, which included fast decay times of 2 ns. Computer simulations predicted absorption and emission wavelengths fairly well, but were of little help for the prediction of brightness, stability, Φf, or decay time.
- Kauffman, Joel M.,Moyna, Guillermo
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p. 839 - 853
(2007/10/03)
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- Synthesis and electroluminescence properties of heterocyclic conjugated copolymers and blends
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Improved electroluminescent efficiencies in polymer light-emitting diodes(LEDs) have been reported to be obtained either by constructing multi-layer devices or by using polymer blends in a light emitting layer. In this work, conjugated copolymers, poly((PZV-PV)-co-(CZV-PV)) containing (N-2-ethylhexyl)-3,6-phenothiazinylene vinylene(PZV) unit and (N-2-ethylhexyl)-3,6-carbazolylene vinylene(CZV) unit in different ratio were synthesized by Horner-Emmons reaction utilizing potassium f-butoxide. Homopolymers, poly(PZV-PV) and poly(CZV-PV) were also synthesized. Polymer LED's fabricated with poly(PZV-PV) and poly(CZV-PV) homopolymers as light emitting layers exhibited EL maximum at 570nm amd 500nm, respectively. LED's made with poly((PZV-PV)-co-(CZV-PV)) copolymers, however, showed EL maxima shifted to longer wavelengths.
- Park, Lee Soon,Ryu, Hyeon Sool,Seo, Hyeon Jin,Kim, Woo Sik,Lee, Dong H.O.,Min, Kyung Eun,Seo, Kwan H.O.,Kang, Inn Kyu
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- Fluorescent bispyrroles. New building blocks for novel π-conjugated polymers
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Several bispyrroles which are bridged through conjugated aromatic moieties were synthesized by the Wittig-Horner-Emmons reaction. Photophysical and electrochemical data of these highly fluorescent monomers reveal that they are useful building blocks for the design of a wide variety of novel π-conjugated polymers, which may find application as potential optoelectronic materials. (C) 2000 Elsevier Science Ltd.
- Eldo,Arunkumar,Ajayaghosh
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p. 6241 - 6244
(2007/10/03)
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- Crown ether substituted 1,4-distyrylbenzenes and their complexation with alkali picrates
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The 1,4-distyrylbenzenes 8 and 9, which contain two crown ether units, each, were prepared by Wittig-Horner reactions. Their complexation tendencies with alkali picrates (Li-Cs) in water/dichloromethane were investigated. Potassium ions give the strongest complexes. Generally monomolecular 1:1-complexes are formed; however, [K-8]+ [Pik]-, [K-9]+ [Pik]- and [Rb-8]+ [Pik]- generate aggregates, for which a stairway structure is proposed. Wiley-VCH Verlag GmbH, 2000.
- Schwoeppe, Dirk,Meier, Herbert
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p. 459 - 464
(2007/10/03)
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- The synthesis of novel bisphosphonates as inhibitors of phosphoglycerate kinase (3-PGK)
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A series of conformationally-restrained analogues of 1,3-bisphospho-D-glyceric acid (1,3-BPG) 1 has been synthesised for use as inhibitors of 3-PGK (E.C. 2.7.2.3). These compounds have non-scissile phosphonate linkages and also incorporate α-halogen substituents to make them isopolar and isosteric mimics of the natural substrate. A monocyclic aryl core between the two phosphoryl centres provides both a rigid framework linking these moieties and loci for further substitution. The compounds were tested against human 3-PGK and found to be good competitive inhibitors. α-Fluorination of the phosphonic acids increased the affinity for the enzyme into the submicromolar range. Correlation of IC50 data with pKa. and pKa, values indicates that the acidity of the phosphoryl group exerts a strong influence on protein binding. The Royal Society of Chemistry 2000.
- Caplan, Neil A.,Pogson, Christopher I.,Hayes, David J.,Blackburn, G. Michael
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p. 421 - 437
(2007/10/03)
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- Synthesis and properties of highly soluble third-order optically nonlinear chromophores and methacrylate monomer based on distyrylbenzene
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A novel series of highly soluble distyrylbenzenes bearing poly(alkyleneoxy) and/or alkylsulfonyl solubilizing substituents has been synthesized using the stereoselective Wadsworth-Emmons reaction as a key step. The corresponding poly(alkyleneoxy) alkylsulfonyl 4,4′-disubstituted distyrylbenzene has been covalently incorporated into an acrylic monomer which has also been successfully co-polymerized with methyl methacrylate (MMA). All the 4,4′-disubstituted distyrylbenzenes and the polyacrylate based co-polymer show excellent solubility, processibility and thermal stability. Importantly, 2-(2-butoxyethoxy)ethoxy-hexylsulfonyl 4,4′-disubstituted distyrylbenzene exhibits only a minor bathochromic shift of the absorption maximum compared to those of the corresponding symmetrically 4,4′-disubstituted distyrylbenzenes; however, its third-order optical nonlinearity derived from Z-scan measurements at 800 nm is approximately twice as large as those of its symmetrically 4,4′-disubstituted counterparts.
- Wong,Samoc,Samoc,Luther-Davies,Humphrey
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p. 2005 - 2009
(2007/10/03)
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- Aliphatic phenylene vinylene copolymers: Tuning the color of luminescence through co-monomer feed ratios
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By introducing co-monomers with flexible linker groups into growth condensation route to poly-(phenylene-alt-vinylene (PPV), a series of solution-processible PPV copolymers is prepared. Peak photoluminescence of these copolymers systematically ranges from about 2.25 to 2.75 eV (yellow-green to blue), increasing in energy upon increasing flexible linker content. Length of the linker group does not significantly alter spectral properties but does influence solubility and film morphology. The statistical distibution of phenylene vinylene segements along the copolymer backbone is discussed in the context of the optical profiles expected. Quantitative quenching of the luminescense for the shortest phenylene vinylene segments strongly indicates that crossover of excited states is occurring. The trapping and recombination of these excited states is occurring on lower-energy "islands", confirmed to be the longer phenylene vinylene segments, which serve as ideal recombination sites for photogenerated species.
- Hay,Klavetter
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p. 7112 - 7118
(2007/10/02)
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