- PHOTORESPONSIVE COMPOUND, AND ADHESIVE, TONER AND IMAGE FORMATION METHOD USING THE SAME
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PROBLEM TO BE SOLVED: To provide a compound that is fluidized by light irradiation and is un-fluidized reversibly, and shows no excessive coloration. SOLUTION: The present invention relates to a compound of chemical formula 1a or 1b: R1 and r1 each denote a hydrogen atom, a halogen atom or the like; R2-R7 and r2-r7 each denote a group represented by chemical formula 2, a hydrogen atom, a halogen atom or the like, where at least one of R2-R7 and r2-r7 is a group represented by chemical formula 2; in chemical formula 2, X1 and X2 each denote N or CH, and X1≠X2; A1-A5 each denote a hydrogen atom, a halogen atom or the like, where at least one of A1-A5 is an alkyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, or an acyloxy group. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0214; 0217-0218
(2021/05/07)
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- PHOTORESPONSIVE LOW-MOLECULAR WEIGHT MATERIAL, ADHESIVE, TONER, AND IMAGE FORMING METHOD
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Disclosed is a compound containing a specific structure having an azomethine part, the compound being reversibly fluidized and non-fluidized by being irradiated with light.
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Paragraph 0385-0386
(2020/08/30)
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- Discovery of Diphenoxy Derivatives with Flexible Linkers as Ligands for β-Amyloid Plaques
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The highly rigid and planar scaffolds with π-conjugated systems have been widely considered to be indispensable for β-amyloid (Aβ) binding ligands. In this study, a library of diphenoxy compounds with different types of more flexible linkers as Aβ ligands were synthesized and evaluated. Most of them displayed good affinity (Ki1-42aggregates, and some ligands even showed values of Kiless than 10 nM. Structure-activity relationship analysis revealed that modification on the linkers or substituents tolerated great flexibility, which challenged the long-held belief that rigid and planar structures are exclusively favored for Aβ binding. Three ligands were labeled by iodine-125, and they exhibited good properties in vitro and in vivo, which further supported that this flexible scaffold was potential and promising for the development of Aβ imaging agents.
- Jia, Jianhua,Zhang, Longfei,Song, Jia,Dai, Jiapei,Cui, Mengchao
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p. 4089 - 4100
(2020/12/13)
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- Thermotropic Liquid-Crystalline and Light-Emitting Properties of Bis(4-aalkoxyphenyl) Viologen Bis(triflimide) Salts
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A series of bis(4-alkoxyphenyl) viologen bis(triflimide) salts with alkoxy chains of different lengths were synthesized by the metathesis reaction of respective bis(4-alkoxyphenyl) viologen dichloride salts, which were in turn prepared from the reaction of Zincke salt with the corresponding 4-n-alkoxyanilines, with lithium triflimide in methanol. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance spectra and elemental analysis. Their thermotropic liquid-crystalline (LC) properties were examined by differential scanning calorimetry, polarizing optical microscopy, and variable temperature X-ray diffraction. Salts with short length alkoxy chains had crystal-to-liquid transitions. Salts of intermediate length alkoxy chains showed both crystal-to-smectic A (SmA) transitions, Tms, and SmA-to-isotropic transitions, Tis. Those with longer length of alkoxy chains had relatively low Tms at which they formed the SmA phases that persisted up to the decomposition at high temperatures. As expected, all of them had excellent thermal stabilities in the temperature range of 330-370 ?C. Their light-emitting properties in methanol were also included.
- Agra-Kooijman, De?a M.,Al-Karawi, Muhammed Kareem M.,Bhowmik, Pradip K.,Chang, Anthony,Chen, Si L.,Cortez, Raymond G.,Dizon, Erenz J.,Fisch, Michael R.,Gutierrez, Bryan,Han, Haesook,Ho, Andy,Killarney, Shane T.,Kim, Jongin,Kumar, Satyendra,Mandal, Hari D.,Mendez, Klarissa,Principe, Ronald Carlo G.,Sharpnack, Lewis
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- Structurally simple trimesic amides as highly selective anion channels
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Trimesic amide molecules, which contain simple alkyl chains in their periphery, exhibit interesting anion-transport functions. The most active and highly selective channel TA12 efficiently transports ClO4? anions across membranes, with other anions conducted in the order of I? > NO3? > Br? > Cl?.
- Yuan, Lin,Shen, Jie,Ye, Ruijuan,Chen, Feng,Zeng, Huaqiang
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supporting information
p. 4797 - 4800
(2019/05/02)
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- Synthesis, liquid crystalline properties and photo switching properties of coumarin-azo bearing aliphatic chains: Application in optical storage devices
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A series of novel azo-coumarin derivatives with different aliphatic chain length (3a-e) have been synthesized and characterized for liquid crystal properties and their photoswitching behavior. The incorporation of coumarin along with azobenzene was prepared via esterification reaction and differ in the length of alkyl group, CnH2n+1, where n = 6, 8, 10, 12 and 14. Azo-coumarin bearing C14 alkyl chain shows Smectic–A phase while azo-coumarin bearing rest of long alkyl chain exhibited Nematic phase. The incorporation of natural product moieties into azobenzene network has increased electron delocalisation and liquid crystal properties. The photoswitching properties of said molecules were tested and the coumarin-azo compounds 3a-e took ~46 s to reach photostationary state during UV illumination and exhibited long thermal back relaxation time (~16 h) in solutions. Device is also fabricated to see the performance of the device with respect to the alkyl chain length. Presented studies show the importance of azo-coumarin derivatives with different chain length for the application of optical storage devices.
- Madiahlagan, Eswaran,B N, Sunil,Ngaini, Zainab,Hegde, Gurumurthy
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- Luminescent mesogenic borondifluoride complexes with the Schiff bases containing salicylideneamines and β-enaminoketones core systems
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Three new families of borondifluoride complexes 1a–c derived from salicylideneamines 2a and β-enaminoketonates 2b–c were reported, and their mesomorphic and optical properties were also investigated. One single crystal and molecular structure of nonmesogenic BF2 complex 1c (n = 10) was resolved and the geometry of the central boron atom was tetrahedron. A larger dihedral angle of 81.3° between the two phenyl rings observed in crystal lattice was attributed to the lack of liquid crystallinity. Boron complexes 1a formed monotropic SmA phases, while boron complexes 1b exhibited enantiotropic SmC mesophases. The optical property of the boron complexes was dependent on their molecular structures, and they emitted a blue–to–green emission at λmax = 476–541 nm in the solution and 488–550 nm in the solid state. This is the first group of mesogenic BF2 complexes with the Schiff bases derived from respective salicylideneamines and β-enaminoketones.
- Lei, Zih-Yang,Lee, Gene-Hsiang,Lai, Chung K.
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- Columnar self-assembly of bowl shaped fluorescent liquid crystals based on calix[4]arene with Schiff base units
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A new family of bowl-shaped molecules with a calix[4]arene rigid core and appended on four-sides, that display a wide range of hexagonal columnar phases, has been synthesised and well characterized. The thermal behaviours of the present compounds were established using a combination of polarising optical microscopy (POM), differential scanning calorimetry (DSC) and a high-temperature powder X-ray diffraction method (XRD). It is found that all of the synthesised materials show an enantiotropic hexagonal columnar liquid crystal phase. The structural and conformation characterization of these newly synthesised compounds was achieved by FT-IR, 1H NMR, and 13C NMR spectroscopy. All of the synthesised compounds exhibited good blue luminescence in solution under long wavelength UV light. To explore the structure property correlations, the alkoxy side chain group was varied from a lower alkyl spacer to a higher alkyl spacer on the lower rim of the calix[4]arene. The present research specified that the introduction of linking groups on the lower rim with an n-alkoxy side group is an influential approach to obtaining a supramolecular bowl shape liquid crystal which has good thermal and photophysical behaviour.
- Sharma, Anuj S.,Sharma, Vinay S.,Vekariya, Rajesh H.
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p. 15044 - 15051
(2018/09/29)
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- Novel Synthetic Monothiourea Aspirin Derivatives Bearing Alkylated Amines as Potential Antimicrobial Agents
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A new series of aspirin bearing alkylated amines moieties 1-12 were synthesised by reacting isothiocyanate with a series of aniline derivatives in overall yield of 16-56%. The proposed structures of all the synthesised compounds were confirmed using elemental analysis, FTIR, and 1H and 13C NMR spectroscopy. All compounds were evaluated for antibacterial activities against E. coli and S. aureus via turbidimetric kinetic and Kirby Bauer disc diffusion method. Compound 5 bearing meta -CH3 substituent showed the highest relative inhibition zone diameter against tested bacteria compared to ortho and para substituent. Furthermore, aspirin derivatives bearing shorter chains exhibited better bacterial inhibition than longer alkyl chains.
- Nordin, Norsyafikah Asyilla,Chai, Tchan Wei,Tan, Bee Ling,Choi, Ching Liang,Abd Halim, Ainaa Nadiah,Hussain, Hasnain,Ngaini, Zainab
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- Synthesis and mesomorphic properties of 2,4-bis(4′-n-pentyloxybenzoyloxy)- benzylidine-4″- n-alkoxyaniline
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The synthesis and mesomorphic properties of a new series of 2,4-bis(4′-npentyloxybenzoyloxy)- benzylidine-4″ -n-alkoxyaniline (DC5An) are reported. The molecular structure of compounds was confirmed by FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis. The mesomorphic properties were studied by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) measurements. All compounds of the series exhibit nematic (N) and smectic C (SmC) phases. The first four homologues (DC5A1-DC5A4) display a N mesophase, whereas the highest homologues (DC5A5-DC5A10) exhibit an enantiotropic dimorphism N and SmC phases. The mesomorphic properties of the present series are compared and discussed with other structurally related series.
- Hamad, Wali M.,Azeez, Hashim J.,Al-Dujaili, Ammar H.
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- AZOBENZENE COMPOUND AND HEAT PUMP SYSTEM USING THE SAME
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PROBLEM TO BE SOLVED: To provide an azobenzene compound capable of repeated structural changes without heating, and a heat pump system using the same. SOLUTION: An azobenzene compound represented by the general formula (1) and undergoing cis-trans isomerization reaction upon light irradiation is used as a heat medium of a heat pump system. In the formula, at least one of R1 to R3 is (CH2CH2O)n-R10; R4 is R11, O-R11, NH-R11, or COO-R11; X- is Cl-, Br-, I-, BF4-, PF6-, CH3(CH2)nSO3-, TsO-, (YSO2)2 N-, or (NC)2 N-; n is an integer between 0 and 2; and Y is F, CF3, or C2F5. COPYRIGHT: (C)2015,JPO&INPIT
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- Photoliquefiable ionic crystals: A phase crossover approach for photon energy storage materials with functional multiplicity
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Ionic crystals (ICs) of the azobenzene derivatives show photoinduced IC-ionic liquid (IL) phase transition (photoliquefaction) upon UV-irradiation, and the resulting cis-azobenzene ILs are reversibly photocrystallized by illumination with visible light. The photoliquefaction of ICs is accompanied by a significant increase in ionic conductivity at ambient temperature. The photoliquefaction also brings the azobenzene ICs further significance as photon energy storage materials. The cis-IL shows thermally induced crystallization to the trans-IC phase. This transition is accompanied by exothermic peaks with a total ΔH of 97.1 kJmol-1, which is almost double the conformational energy stored in cisazobenzene chromophores. Thus, the integration of photoresponsive ILs and self-assembly pushes the limit of solar thermal batteries.
- Ishiba, Keita,Morikawa, Masa-Aki,Chikara, Chie,Yamada, Teppei,Iwase, Katsunori,Kawakita, Mika,Kimizuka, Nobuo
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p. 1532 - 1536
(2015/02/05)
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- AZOBENZENE COMPOUND AND HEAT PUMP SYSTEM USING IT
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PROBLEM TO BE SOLVED: To provide an azobenzene compound capable of changing a structure repeatedly without heating and a heat pump system using it. SOLUTION: An azobenzene compound expressed by the formula (1) and reacts by cis-trans isomerization by light radiation, is used as a heat medium of a heat pump system. The azobenzene compound expressed by the formula (1) is subjected to endotherm by melting latent heat when phase change from a solid phase trans body to a liquid phase cis body occurs, and is subjected to heat evolution when phase change from the liquid phase cis body to the solid phase trans body occurs. COPYRIGHT: (C)2015,JPO&INPIT
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- Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors
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A series of new low molecular organogelators (LMOGs) with thermotropic mesophase were synthesized via the reaction of 3,6-dimethyl-pyrazine-2,5- dicarboxylic acid with p-alkoxyl anilines. These compounds readily formed stable gels in a variety of organic solvents and their self-assembly behavior, structure-property relationship were investigated by scanning electron microscopy (SEM), X-ray diffraction (XRD), 1H nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR) and ultra-violet-visible spectroscopy (UV). The results showed a combination of intra-hydrogen bonding, π-π stacking and van der Waals interaction resulted in the aggregation of the organogelators to form three-dimension fibrous networks. The gels formed were multi-responsive to environmental stimuli, such as temperature, fluorinion, and shear stress. More importantly, all the organogelators exhibited thermotropic hexagonal column mesophase as revealed by differential scanning calorimetry (DSC), polarized optical microscopy (POM), and variable temperature XRD studies. A control compound was synthesized and its gelling ability was also checked.
- Huang, Yao-Dong,Tu, Wei,Yuan, Yu-Qin,Fan, Dong-Li
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supporting information
p. 1274 - 1282
(2014/02/14)
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- Reduction of nitrobenzene derivatives using sodium borohydride and transition metal sulfides
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Reported here is the reduction of aromatic nitro compounds using sodium borohydride and transition metal sulfides as catalysts. The reaction conditions were optimized using the reduction of nitrobenzene as a model reaction. The catalysts studied were iron sulfide (Fe3S4), copper sulfide (CuS), zinc sulfide (ZnS), cobalt sulfide (Co3S4), and nickel sulfide (NiS). The reduction was monitored using gas chromatography. Quantitative conversions were achieved using Co3S4 and NiS, representing a ten-fold increase in reactivity compared to the non-catalyzed reaction. Fe3S4 and ZnS had no apparent effect on the reduction of nitrobenzene while the reduction using CuS showed a marginal increase. The reduction method was applied to several aryl-nitro derivatives containing either electron-withdrawing or electron-donating groups. Halogen containing aryl-nitro compounds were reduced without dehalogenation. The reduction had no effect on other functional groups such as carboxylic acids, esters, amides, or alkenes, indicating that the reduction is highly chemoselective.
- Pi?a, Samuel,Cedillo, Diana M.,Tamez, Carlos,Izquierdo, Nezhueyotl,Parsons, Jason G.,Gutierrez, Jose J.
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supporting information
p. 5468 - 5470
(2014/12/11)
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- Gold nanoparticles decorated by clustered multivalent cone-glycocalixarenes actively improve the targeting efficiency toward cancer cells
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A novel approach for multivalent targeting by using gold nanoparticles noncovalently decorated by tight functionalization with a cone-glycocalixarene bearing four mannose units is reported. The targeting efficiency of these multivalent nanoparticles is shown to be remarkably improved compared to that of nanoparticles bearing a monovalent mannosylated derivative. This journal is the Partner Organisations 2014.
- Avvakumova, Svetlana,Fezzardi, Paola,Pandolfi, Laura,Colombo, Miriam,Sansone, Francesco,Casnati, Alessandro,Prosperi, Davide
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supporting information
p. 11029 - 11032
(2014/11/07)
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- AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY
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Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.
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Page/Page column 121
(2014/08/19)
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- Structure-property correlation of benzoyl thiourea derivatives as organogelators
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A series of N-benzoyl-N′-aryl thiourea derivatives (1-4) can form stable gels from a variety of organic solvents ranging from protic to aprotic or polar to apolar at concentrations below 5 mg/mL. The gelation properties and structures of the resulting gels were investigated by 1H-NMR, FTIR, UV-vis, SEM, and XRD. The gels were anion-responsive and the driving forces for its formation were the hydrogen bonding and van der Waals interaction. The SEM images of the xerogels prepared from the organogels formed in acetonitrile, cyclohexane and acetone showed a network of elongated fibers. The results of XRD suggested that the dry gels had a layer structure.
- Huang, Yao-Dong,Dong, Xue-Lin,Zhang, Li-Li,Chai, Wei,Chang, Ji-Young
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- Liquid-crystalline polymorphism of 4-heptyloxybenzylidene-4′- alkyloxyanilines and their phase equilibrium with 4-octyloxyphenyl 4-nitrobenzoate
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This paper describes the synthesis and liquid-crystalline properties of the homologous series of 4-heptyloxybenzylidene-4′-alkyloxyanilines (7-n). Six of them are presented for the first time. Based on the polarization microscopy (POM and TOA methods) and the calorimetric (DSC) measurements following polymorphism has been detected: nematic, smectic C and smectic I mesophases. The presence of these mesophases was confirmed by the miscibility method, using 4-octyloxyphenyl 4-nitrobenzoate and terephtal-bis (4-butyloaniline) as a mesophase references. Extraordinary results have been found in the mixtures of the investigated compounds with 4-octyloxyphenyl 4-nitrobenzoate; Induced smectic A has been observed, which is connected with very strong intermolecular interactions. Additionally destabilization of nematic and smectic C phases was visible.
- Godzwon, Joanna,Sienkowska, Monika J.,Galewski, Zbigniew
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scheme or table
p. 75 - 82
(2012/04/04)
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- The synthesis and NLO properties of 1,8-naphthalimide derivatives for both femtosecond and nanosecond laser pulses
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Four 1,8-naphthalimide derivatives were synthesized for new nonlinear optical(NLO) materials. Hydrazone group as a p-π structure was introduced into the molecule to extend conjugation and produce NLO properties. Their linear and nonlinear optical (NLO) properties were studied in details. The results show that these compounds possess strong excited-state absorption (ESA) properties and optical limiting with nanosecond laser pulses at 532 nm. Moreover, they also preserve the luminescence originated from naphthalimide and two-photon absorption (TPA) behaviour which can be observed under femtosecond laser pulses ranged from 750 to 870 nm. The broad-band optcial limiting properties of these compounds indicate that they can be potentially applicated in optical limiting materials.
- Ye, Gao-Jie,Zhao, Ting-Ting,Jin, Zheng-Neng,Gu, Pei-Yang,Mao, Jia-Yuan,Xu, Qing-Hua,Xu, Qing-Feng,Lu, Jian-Mei,Li, Na-Jun,Song, Yin-Ling
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scheme or table
p. 271 - 277
(2012/05/04)
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- Supramolecular hydrogels based on antimycobacterial amphiphiles
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Synthetic modification of antimycobacterial 4-alkoxy-anilines yields low molecular weight amphiphiles. The bioactivity is retained in these amphiphiles and shows alkyl chain length specificity. The self-assembly behaviour in aqueous media was investigated
- Bernet, Andreas,Behr, Marina,Schmidt, Hans-Werner
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body text
p. 4873 - 4876
(2012/08/13)
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- A molecular insight on the supramolecular assembly of thiophene polymers
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Herein, the relationship between supramolecularly self-assembled microstructures and the chemical structures of photoluminescent molecules is discussed. A series of non-amphiphilic molecules with different length alkyl chains (4-14), central mesogenic groups, and chemical linkers were designed and synthesized. Intricate analysis shows that the supramolecular assembly varies with change in torsion angle of the thiophene linking group on elongation of the alkyl chain. Small angle X-ray scattering measurement shows long range molecular interaction for lower alkyl chain length, AFM reveals circular domains for octyl and decyl alkyl group polymers. UV-Visible and photoluminescence studies in solution and thin-film show that the J-aggregate patterns for the circular domain of the polymer backbone has a major effect on the polymer absorbance, and produces a larger shift for the photoluminescence signals at higher wavelengths. Excitation polarisation studies show a change in molecular ordering in various colour regions with change in aggregation by means of maximum dichroic ratio for the circular domain assembly. Charge carrier mobility and cyclic voltammetry studies show higher mobility and reduced band gap for these circular domain polymers. Dynamic light scattering studies of octyl alkyl chain polymers show a bimodal distribution, which shows the apparent nature of anisotropy in solution. The Royal Society of Chemistry.
- Suryanarayanan, Chandrasekaran,Ravindran, Ezhakudiyan,Ananthakrishnan, Soundaram Jeevarathinam,Somanathan, Narayanasastri,Mandal, Asit Baran
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p. 18975 - 18982
(2012/10/29)
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- Synthesis of novel triarylamine-based dendrimers with N4,N 6-dibutyl-1,3,5-triazine-4,6-diamine probe for electron/energy transfers in H-bonded donor-acceptor-donor triads and as efficient Cu 2+ sensors
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Two novel highly soluble triarylamine dendrimers TPAD1 and TPAD2 with N4,N6-dibutyl-1,3,5-triazine-4,6-diamine probe were synthesized via normal synthetic routes. Both dendrimers (TPAD1 and TPAD2) form H-bonded donor-acceptor-donor (D-A-D) supramolecular triads TPAD1-PBI-TPAD1 and TPAD2-PBI-TPAD2 with 3,4,9,10-perylene tetra carboxylic diimide derivative (PBI). The presence of multiple H-bonds in the solution state was elucidated by 1H NMR titrations and IR spectral studies. J-aggregations and electron/energy transfers provided by both dendrimers were verified by UV-Vis and photoluminescence (PL) titrations with PBI and the particle sizes of supramolecular triads were calculated by X-ray diffraction (XRD) analysis. Similarly, both dendrimers also showed sensitivities towards Cu2+ in comparison with 19 interfering metal ions, which were evidenced via UV-Vis and PL titraions in both single and dual metal systems. The maximum detection limit of Cu2+ ions was determined to be 20 ppm from PL titrations for both dendrimers, and the 1:2 stoichiometry of the complexes formed by both dendrimers (TPAD1-Cu2+ and TPAD2-Cu2+) were calculated by Job plots based on UV-Vis absorption titrations. More importantly, the binding mechanism of the 1,3,5-triazine-4,6-diamine probe of both dendrimers was well characterized by 1H and 13C NMR titrations ([D 8]THF:D2O = 2:1 in vol.) and supported by the fluorescence reversibility by adding metal ions and PMDTA sequentially.
- Shellaiah, Muthaiah,Rajan, Yesudoss Christu,Lin, Hong-Cheu
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p. 8976 - 8987
(2013/01/13)
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- Studies of calamitic liquid crystalline compounds involving ester-azo central linkages with a biphenyl moiety
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Two mesogenic homologous series involving ester-azo central linkages with a biphenyl moiety have been synthesized, such as 4'-[(4-n-alkoxyphenyl)diazenyl] biphenyl-4-ol (series I) and 4'-[(4-n-alkoxyphenyl) diazenyl]-4-butoxy phenyl biphenyl-4-carboxylate (series II). Azobiphenyl of series I having a free hydroxyl group with strong hydrogen bonding exhibits a high-temperature enantiotropic smectic phase. Whereas in series II, compounds containing C 1-C8 carbon atoms exhibit only a monotropic smectic phase and compounds with C10, C12, C14, and C 16 atoms show an enantiotropic smectic phase. These compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral studies. The phase transition and mesogenicity of these substances were studied by polarizing optical microscopic and differential scanning calorimetric techniques. Their thermal stabilities and other characteristics are discussed. Copyright Taylor &Francis Group, LLC.
- Thaker,Dhimmar,Patel,Solanki,Patel,Chothani,Kanojiya
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p. 172 - 191
(2012/07/27)
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- Bulk heterojunction solar cells based on a low band gap soluble bisazopyrrole and the corresponding BF2-azopyrrole complex
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The diazonium salt derived from 4-(hexyloxy)benzamine reacted with half an equivalent of pyrrole to afford 2,5-bis(4-hexyloxyphenylazo)-1H-pyrrole (A). The reaction of the latter with BF3·Et2O gave the corresponding BF2-azopyrrole complex (B). The thin film absorption spectra of A and B were broad and extended into the near infrared region with optical band gaps of 1.54 and 1.49 eV, respectively. The photovoltaic properties have been investigated using blends of A or B with PCBM, and it was found that the device based on B:PCBM showed higher power conversion efficiency (PCE) in comparison to that for the device with A:PCBM blend. This has been attributed to the higher hole mobility and lower band gap of B relative to A. The effect of different thermal annealing on the photovoltaic response of the devices has been investigated and it was found that the contact annealed device displayed PCE of approximately 2.7% and 3.15% for A:PCBM and B:PCBM blends, respectively. The increase in the PCE for the contact annealed device has been interpreted in terms of more balanced charge transport.
- Mikroyannidis,Kabanakis,Tsagkournos,Balraju,Sharma
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scheme or table
p. 6464 - 6471
(2010/09/06)
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- Role of terminal heterocyclic ring on mesomorphic properties of homologous series
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Two new homologous series of compounds with a heterocyclic ring having sulfur and oxygen as a hetero atom derived from p-hydroxy acetophenone and alkoxy aniline containing cinnamate-azomethine as central linkages have been synthesized. viz. 4(furalacryloxy) α-methyl benzylidine-4′-alkoxy aniline and 4(thianylacryloxy) α-methyl benzylidine-4′-alkoxy aniline. The compound of both the series have been characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectrometry method. Their liquid crystalline properties have been investigated by optical polarizing microscopy and differential scanning calorimetry (DSC) studies. All the derivatives are mesomorphic in nature showing the nemetic phase. The mesomorphic properties of the present two series are compared with other structurally related series to evaluate the effect of thiophene and furan on mesomorphism. Copyright Taylor & Francis Group, LLC.
- Thaker,Patel,Solanki,Dhimmer,Dave
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experimental part
p. 63 - 80
(2010/09/05)
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- Azomesogens having a lateral hydroxy substituent
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Two homologous series of liquid crystalline azoesters consisting of a lateral hydroxyl substituent on the central benzene ring at 2' positions have been synthesized and thermally characterized. All the 24 members, of both series, exhibit high temperature nematic phases. All the compounds of both series are thermally stable and exhibit a wide mesomorphic range. The homologues have been characterized using Infra Red (IR), Nuclear Magnetic Resonance Spectroscopy (NMR), and Differential Scanning Calorimetry (DSC). Their mesomorphic properties and other characteristics are discussed.
- Dixit, Sandhya,Vora
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experimental part
p. 43 - 52
(2010/04/02)
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- Synthesis of symmetric liquid crystal dimers based on azo and imine groups and investigation of phase behaviour by varying alkoxy terminal chain length
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With the objective to study the effect of alkoxy terminal chain length on mesomorphic properties of liquid crystals, we have synthesized two (Azo and Imine) different series of dimesogens by varying terminal alkoxy chain length (n = 6-12) with a short spacer unit in between two mesogens. Transition temperatures and phase characterization were studied by DSC, POM and XRD analysis. It was found that all the dimers show mesomorphic properties and the change in terminal alkoxy chain length has pronounced effect on the smectic phase window. In the DSC cooling scan, the smectic phase window of azo compounds increased from 6.4°C (2A6) to 16.0°C(2A12), whereas in Schiff base compounds, it increased from 9.2°C (2S6) to 31.0°C(2S12). Further, the 2A11 dimer was found to undergo photo induced configurational changes.
- Kim, Tae Hyeong,Lee, Chang Sin,Ramaraj,Jeon, Hye Jin,Song, Hyun Hoon,Lee, Soo Min,Yoon, Kuk Ro
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experimental part
p. 102 - 116
(2010/03/04)
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- Smectic polymorphism of 4-nonyloxybenzylidene-4′-alkyloxyanilines
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This paper describes liquid-crystalline polymorphism of the homologous series of 4-nonyloxybenzylidene-4′-alkyloxyanilines. Based on the polarization microscopy (POM, TOA) and the calorimetric (DSC) measurements the following mesophases were detected: nematic, smectic A, smectic C, smectic B, smectic I and smectic G. The presence of these mesophases was confirmed by the miscibility method, using: 4-heptyloxybenzilidene-4′-pentylaniline, 4-hexyl-4′-decyloxyazobenzene and 4-nonyloxybenzilidene-4′-butylaniline as mesophase references. Influence of the alkyl chain length on the type of mesophases and entropic effects of phase transition are discussed.
- Godzwon, Joanna,Sienkowska, Monika J.,Galewski, Zbigniew
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p. 259 - 267
(2008/03/13)
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- Discotic liquid crystalline hydrazone compounds: Synthesis and mesomorphic properties
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1,3,5-Trisacetoacetamidobenzene with three 1,3-diketo groups was synthesized by the reaction of 1,3,5-triaminobenzene with diketene. Discotic hydrazone compounds were prepared by the diazo coupling reaction between 1,3,5-trisacetoacetamidobenzene and diazonium salts of 4-alkyloxyphenylamines. The compounds existed in hydrazone forms exclusively, being stabilized by the intramolecular hydrogen bonds, and showed discotic nematic or columnar hexagonal mesophases.
- Jeong, Min Ju,Park, Jun Ha,Lee, Changjin,Chang, Ji Young
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p. 2221 - 2224
(2007/10/03)
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- Organosoluble copper clusters as precatalysts for carbon - Heteroelement bond-forming reactions: Microwave and conventional heating
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(Chemical Equation Presented). The coupling of aryl iodides with alcohols under mild conditions has been explored using self-assembled octanuclear copper clusters as catalysts. Reactions involving tetrahydrofurfuryl alcohol were typically complete in 4-8
- Manbeck, Gerald F.,Lipman, Adam J.,Stockland Jr., Robert A.,Freidl, Adrienne L.,Hasler, Amy F.,Stone, Joshua J.,Guzei, Ilia A.
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p. 244 - 250
(2007/10/03)
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- Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides
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Using N-[4-(hexyloxy)phenyl]piperidine-3-carboxamide (17c) as a structural lead, a number of isomers, derivatives, and ring-opened analogs were synthesized and tested for their ability to block the in vitro aggregation of human platelets induced by adenosine 5′-diphosphate (ADP). For the most active compounds, inhibition of the platelet aggregation triggered by arachidonic acid (AA) and ADP-induced intraplatelet calcium mobilization was also demonstrated. Based on quantitative structure-activity relationships (QSARs), we proved the impact of hydrophobicity on antiplatelet activity by a nonlinear (parabolic or bilinear) relationship between pIC50 and lipophilicity, as assessed by RP-HPLC capacity factors and Clog P (i.e. calculated 1-octanol-water partition coefficients). This study highlighted the following additional SARs: quasi-isolipophilic isomers of 17c (isonipecotanilides and pipecolinanilides) and ring-opened analogs (e.g. anilide of β-alanine) exhibited lower antiplatelet activity; methylation of the piperidine nitrogen of 17c has no effect, whereas alkylation with an n-propyl group decreases the activity by a factor of approximately 2, most likely due to a conformation-dependent decrease in lipophilicity.
- De Marco, Agostino,De Candia, Modesto,Carotti, Andrea,Cellamare, Saverio,De Candia, Erica,Altomare, Cosimo
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p. 153 - 164
(2007/10/03)
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- Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport
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The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl ketoglutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612)1 and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquinolinedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (Ki = 167 μM), 6-PhCH2CH2-QDC (Ki = 143 μM), 6-(4′-phenylstyryl)-QDC (Ki = 64 μM), and 6-biphenyl-4-yl-QDC (Ki=41 μM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.
- Carrigan, Christina N.,Bartlett, Richard D.,Esslinger, C. Sean,Cybulski, Kimberly A.,Tongcharoensirikul, Pakamas,Bridges, Richard J.,Thompson, Charles M.
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p. 2260 - 2276
(2007/10/03)
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- Mesogenicity of organophosphazenes: The effect of phosphazene rings and side groups on the phase transition
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Cyclotriphosphazene and cyclotetraphosphazene derivatives with mesogenic 4-N-(4-alkoxyphenyl)iminomethyl)phenoxy and 4-(4′-alkoxy) biphenoxy moieties were synthesized. Schiff base moiety has higher mesomorphic stability than that in biphenyl moiety both in cyclotriphosphazene and cyclotetraphosphazene. Cyclotriphosphazenes possess higher thermal stability in the mesomorphic phase than the cyclotetraphosphazenes, suggesting the difference in the molecular structure.
- Moriya, Keiichi,Yamane, Toshihiro,Suzuki, Toshiya,Masuda, Tsuyoshi,Mizusaki, Hiroshi,Yano, Shinichi,Kajiwara, Meisetsu
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p. 1427 - 1432
(2007/10/03)
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- Synthesis and structure of 1,4-diazabutadiene liquid crystals
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Nine 1,4-diazabutadiene compounds, Ar-N=C(R)-C(R)=N-Ar, R=H, Me; Ar= H2n+1CnO-C6H4, 2,4-(H9C4O)(Me)-C6H3 were synthesized and their liquid crystal properties were studied through thermal polarizing microscopy. The X-ray single crystal structure of compound 9 (Ar-N=C(H)-C(H)=N-Ar, Ar=2,4-(Me)(H9C4O)C6H3) was tested. It is a monoclinic crystal system, space group P21/C with the unit cell parameters: a=7.0703(3)A, b=8.674(4)A, c=18.3115(8)A, β =95.392(1)°. V=1114.57(9)A3, z=2, Dc=1.134 Mg/m3, R=0.0490,Rw=0.1237.
- Zhao, Ke-Qing,Hu, Pin,Xu, Hong-Bo
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p. 801 - 808
(2007/10/03)
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- New synthetic method of aromatic ethers under microwave irradiation in dry media
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Under microwave irradiation a number of phenols react remarkably fast with a number of primary alkyl halides to give aromatic ethers.
- Bogdal, Dariusz,Pielichowski, Jan,Boron, Adam
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p. 3029 - 3039
(2007/10/03)
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- Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines
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Members of the class of 9-anilinoacridine topoisomerase II inhibitors bearing lipophilic electron-donating 1'-aniline substituents are active against both the promastigote and amastigote forms of the parasite Leishmania major. A series of analogues of the known 1'-NHhexyl lead compound were prepared and evaluated against L. major in macrophage culture to further develop structure-activity relationships (SAR). Toxicity toward mammalian cells was measured in a human leukemia cell line, and the ratio of the two IC50 values (IC50(J)/IC50(L)) was used as a measure of the in vitro therapeutic index (IVTI). A 3,6-diNMe2 substitution pattern on the acridine greatly increased toxicity to L. major without altering mammalian toxicity, increasing IVTIs over that of the lead compound. The 2-OMe, 6-C1 acridine substitution pattern used in the antimalarial drug mepacrine also resulted in potent antileishmanial activity and high IVTIs. Earlier suggestions of the utility of 2'-OR groups in lowering mammalian cytotoxicity were not borne out in this wider study. A series of very lipophilic 1'-NRR (symmetric dialkylamino)-substituted analogues showed relatively high antileishmanial potency, but no clear trend was apparent across the series and none were superior to the 1'-NH(CH2)5Me subclass. Subsets of the most active 1'- N(R)(CH2)5Me- and 1'-N(alkyl)2-substituted compounds against L. major were also evaluated against Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, but no consistent SAR could be discerned in these physiologically diverse test systems. The present study has confirmed earlier conclusions that lipophilic electron-donating groups at the 1'-position of 9- anilinoacridines provide high activity against L. major, but the SAR patterns observed do not carry over to the other parasites studied.
- Gamage, Swarna A.,Figgitt, David P.,Wojcik, Stanley J.,Ralph, Raymond K.,Ransijn, Adriana,Mauel, Jacques,Yardley, Vanessa,Snowdon, Diane,Croft, Simon L.,Denny, William A.
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p. 2634 - 2642
(2007/10/03)
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- Mesogenic 4-(2,3-Epoxypropoxy)-4'-alkoxyazoxybenzenes
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Optimal conditions for preparation of 4-(2,3-epoxypropoxy)-4'-alkoxyazoxybenzenes were developed, and 10 mesogenic homologs (n = 1-10) possessing an extended nematic mesophase were synthesized.Nonyloxy and decyloxy derivatives of epoxyazoxybenzene exhibit also smectic mesomorphism.
- Burmistrov, V. A.,Kuz'mina, S. A.,Koifman, O. I.
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p. 351 - 353
(2007/10/03)
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- Mesogenic properties of liquid crystals having a chiral semiflexible joint
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Two homologous series of mesogenic enantiomers with chiral semiflexible joint, -C*H(CH3)CH2COO-, are examined. High twist power and presence of blue phases with short lattice period are found for eleven examined compounds. Some effects of chirality in reentrant system are discussed. On phase diagram of enantiomers the SmAd phase area is shifted toward longer homologues as compared to racemates. In result, an island of the SmAd phase in the cholesteric sea exists on binary phase diagrams of R- and S- enantiomers. Triple divergence of the pitch in the cholesteric phase of a pure compound is observed.
- Gorecha,Pyzuk,Mieczkowski
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