- Development of new nonlinear optical polymers based on epoxy- amine oligomers with Bi-chromophore fragments in the side chain
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For the first time bichromophore nonlinear optically active compounds, 3,5-bis [2- (N-ethyl-4- (4′-nitrophenylazo) anilino) ethoxy] benzyl alcohol, DF1, and 3,5-bis [6- (N-methyl-4- (4′-nitrophenylazo) anilino) hexaoxy] benzyl alcohol, DF2, have been synthesized. The synthesis of the epoxy-amine oligomers containing DF1 and DF2 dendritic fragments in the side chain was preceded by molecular design which demonstrated that the hexyl groups, binding the chromophores to the branching center in DF2, are able to provide greater mobility of the chromophores compared to the ethyl groups in DF1, thus determining the preference of the former from the viewpoint of NLO activity. Bi-chromophore compounds were introduced into the side chain of epoxy amine oligomers using the esterification reaction under mild conditions by the Steglich method. As a result, oligomers OAB-DF1 (Tg = 122 °C) and OAB-DF2 (Tg = 107 °C) were obtained with good yields, the degree of functionalization was 60 mol% and 45 mol%, respectively. The values of the NLO coefficients, d33, were measured by second harmonic generation technique; they are equal to 29 pm/V for OAB-DF1 and 40 pm/V for OAB-DF2.
- Nazmieva, Gulshat N.,Vakhonina, Tatiana А.,Ivanova, Nataliya V.,Sharipova, Anastasiya V.,Fominykh, Olga D.,Smirnov, Maxim A.,Balakina, Marina Yu,Sinyashin, Oleg G.
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p. 253 - 265
(2018/07/13)
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- New polymethacrylic nonlinear optical materials containing multichromophores in the side chain
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New polymer materials based on methacrylic copolymers with chromophore-containing dendritic fragments in the side chain have been obtained. The nonlinear optical coefficients of 22, 23 and 28 pm V–1 have been determined for polymers with 18, 21 and 30 mol% content of dendritic fragments, respectively.
- Vakhonina, Tatyana A.,Kadyrova, Alfira A.,Sarvarov, Timur M.,Smirnov, Maksim A.,Ivanova, Nataliya V.,Khamatgalimov, Ayrat R.,Balakina, Marina Yu.,Sinyashin, Oleg G.
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p. 272 - 274
(2018/06/01)
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- New "X-type" second-order nonlinear optical (NLO) dendrimers: Fewer chromophore moieties and high NLO effects
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New types of "X-type" NLO dendrimers, C2 and C3, in which the chromophore moieties were arranged in order, were rationally designed. The special topology of the chromophore moieties contributed a great deal to the good NLO performance of C2 and C3: the d33 value of C2 (containing only five chromophore moieties) was 157.4 pm V-1, while that of C3 (containing nine chromophore moieties) achieved 195.2 pm V-1, much larger than that of C1 (74.7 pm V-1, containing three chromophore moieties) and the fifth generation dendrimer (G5) (193.1 pm V-1, bearing 62 pieces of chromophore moieties). Through careful experimental and theoretical analysis, their structure-property relationship was explained, and discussed in detail.
- Tang, Runli,Zhou, Shengmin,Xiang, Wendi,Xie, Yujun,Chen, Hong,Peng, Qian,Yu, Gui,Liu, Binwen,Zeng, Huiyi,Li, Qianqian,Li, Zhen
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supporting information
p. 4545 - 4552
(2015/05/13)
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- Novel ROS-activated agents utilize a tethered amine to selectively target acute myeloid leukemia
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This study explores the possible use of reactive oxygen-activated DNA modifying agents against acute myeloid leukemia (AML). A key amine on the lead agent was investigated via cytotoxicity assays and was found necessary for potency. The two best compounds were screened via the NCI-60 cell panel. These two compounds had potency between 200 and 800 nM against many of the leukemia cancer cell types. Subsequent experiments explored activity against a transformed AML model that mimics the molecular signatures identified in primary AML patient samples. A lead compound had an IC50 of 760 nM against this AML cell line as well as a therapeutic index of 7.7 ± 3 between the transformed AML model cell line and non-cancerous human CD34+ blood stem/progenitor cells (UCB). The selectivity was much greater than the mainstays of AML treatment: doxorubicin and cytarabine. This manuscript demonstrates that this novel type of agent may be useful against AML.
- Bell-Horwath, Tiffany R.,Vadukoot, Anish K.,Thowfeik, Fathima Shazna,Li, Guorui,Wunderlich, Mark,Mulloy, James C.,Merino, Edward J.
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supporting information
p. 2951 - 2954
(2013/06/27)
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- ROS-Activated Compounds as Selective Anti-Cancer Therapeutics
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Provided are compounds according to the following Formula I: The Formula I compounds are activated in the presence of reactive oxygen species (ROS) and are therefore selective anti-cancer therapeutics for cancers associated with elevated ROS. Also provided are methods and pharmaceutical compositions for treating cancers associated with increased ROS.
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Paragraph 0125; 0152
(2013/09/12)
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- Water-soluble, deep-red fluorescent squaraine rotaxanes
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Eight fluorescent squaraine rotaxanes with deep-red absorption/emission wavelengths were prepared and assessed for chemical stability and suitability as water-soluble, fluorescent tracers. The most stable squaraine rotaxanes have four large stopper groups attached to the ends of the encapsulated squaraine, and two members of this structural class have promise as highly fluorescent tracers with rapid renal clearance and very low tissue uptake in living mice.
- Cole, Erin L.,Arunkumar, Easwaran,Xiao, Shuzhang,Smith, Bryan A.,Smith, Bradley D.
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supporting information; experimental part
p. 5769 - 5773
(2012/08/28)
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- Oxidatively activated DNA-modifying agents for selective cytotoxicity
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DNA-modifying agents are stalwarts of chemotherapeutic cancer treatments, but require significant design improvements to improve selectivity, minimize side effects, and for their widespread use to continue. Herein we present a novel design strategy in which DNA-modifying agents contain an oxidizable leaving group and a nitrogen mustard. The agents form strong electrophiles specifically when oxidized. Activation, measured by hydrolysis, illustrates that oxidants increase reactivity 1700-fold. Reaction in the presence of 2'-deoxyguanosine leads to the formation of lesions. Cytotoxicity measured in HeLa cells showed that low IC50 values require an oxidizable hydroquinone and a nitrogen mustard fragment. Cytotoxicity measurements in 15 cancer cell lines demonstrates that oxidatively activated DNA-modifying agents are highly selective, as the analogue tested has IC50 values less than 10μM for only three of the 15 cell lines; in contrast, cisplatin is highly toxic to 13 of the 15 cell lines. The selective cytotoxicity of oxidatively activated DNA-damaging agents could be useful against kidney cancer cells, as the 786-O cell line model assay resulted in an IC50 value of 5μM. DNA-modifying agents require design improvements to lower side effects. A novel design strategy in which agents that contain oxidizable leaving groups is shown. Oxidation increases reactivity 1700-fold. Reactions occur between the agent and 2'-deoxyguanosine, and compounds in this class selectively target the renal carcinoma model cell line 786-O.
- Li, Guorui,Bell, Tiffany,Merino, Edward J.
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experimental part
p. 869 - 875
(2012/01/06)
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- Hyperbranched azo-polymers synthesized by azo-coupling reaction of an AB2 monomer and postpolymerization modification
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A series of hyperbranched azo-polymers have been synthesized by two-stage azo-coupling reactions, in which a hyperbranched precursor azo-polymer (HPAP) was prepared by step-growth polymerization of an AB2 monomer through azo-coupling reaction and then was further modified by postpolymerization azo-coupling reaction at the peripheral groups. The AB2 monomer, di[2-(N-ethylanilino)ethyl]-5-aminoisophthalate, was synthesized from the nucleophilic substitution reaction between N-ethyl-N-(2-chloroethyl)aniline and 3,5-bis(carboxyl)aniline. On the basis of the monomer, HPAP was prepared by step-growth polycondensation of the diazonium salt of the AB2 monomer. The hyperbranched precursor polymer was then reacted with diazonium salts of 4-nitroaniline, 4-aminobenzoic acid, and 4-aminobenzonitrile to introduce different types of donor-acceptor azo-chromophores at the peripheral positions. The structure and properties of the azo-polymers were characterized by the spectroscopic methods and thermal analysis. The hyperbranched azo-polymers were used to fabricate surface relief gratings (SRGs) by exposing spin-coated thin films of the polymers to an interference pattern of Ar + laser beams at modest intensity (150 mW/cm2). The type of electron-withdrawing groups in the parapositions of the terminal azobenzene units shows a significant effect on the SRG inscription rate. The synthetic scheme demonstrated in this work is a feasible way to prepare a variety of hyperbranched azo-polymers under extremely mild conditions. The hyperbranched azo-polymers can potentially be used for applications such as reversible optical data storage, photoswitching, sensors, and other photodriven devices.
- Che, Pengchao,He, Yaning,Wang, Xiaogong
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p. 8657 - 8663
(2008/02/02)
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- Sequentially adsorbed electrostatic multilayers of branched side-chain polyelectrolytes bearing donor-acceptor type azo chromophores
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Two newly synthesized polyelectrolytes (PBANT-AC and PBACT-AC) functionalized with branched side chains bearing electron donor-acceptor type azobenzene chromophores were used as polyanions to build up multilayer films through an electrostatic sequential adsorption process by using poly(diallyldimethylammonium chloride) (PDAC) as the polycation. When dissolved in anhydrous DMF and a series of DMF-H2O mixed solvents with different DMF to H2O ratios, both azo polyelectrolytes could form uniform multilayer films through the layer-by-layer adsorption process. Altering the water content of the dipping solutions of both azo polyelectrolytes was found to dramatically change the thickness of the sequentially adsorbed bilayers, chromophore orientation, and surface roughness of the multilayer films. On the other hand, the solvent effect on the H-aggregation in the multilayer films was determined by the structural details of the azo polyelectrolytes. After the irradiation with a linearly polarized Ar+ laser beam at 488 nm, significant dichroism was induced in the PBANT-AC/PDAC multilayer films prepared from the DMF dipping solution. Upon exposure to an interference pattern of Ar+ laser beam at modest intensities, optically induced surface modulation on the multilayer surfaces was observed.
- Wang, Haopeng,He, Yaning,Tuo, Xinlin,Wang, Xiaogong
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p. 135 - 146
(2007/10/03)
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- Bis(4-((chloro substituted phenyl)azo)anilino methylenes
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There are described novel yellow to red azo compounds of the formula I STR1 wherein each D independently of the other is the radical of an aromatic or heterocyclic diazo component, each Z independently of the other is hydrogen or a C1 -C4 -alkyl group or an acylamino group, Y is hydrogen or an unsubstituted or substituted C1 -C6 -alkyl group, X is either the direct bond or C1 -C6 -alkylene, STR2 and n is a number from 2 to 6, preferably 2; and the substituent Y, in the case of an unsubstituted or substituted C1 -C6 -alkyl group, can also be bonded to the o-position relative to the N atom of the phenylene group to form a six-membered ring, or both Y substituents can be linked together to form a C1 -C6 -alkylene bridge; described also are processes for producing the novel compounds, and their use as dyes for dyeing and printing natural and synthetic textile materials, particularly polyamide and wool materials, and also cotton, whereby there are obtained dyeings which are distinguished by good general fastness properties, especially by a good dye build-up, very good fastness to wet processing, good fastness to light, and good resistance to formaldehyde and good stability to hydrolysis.
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