- Supramolecular enantiomeric and structural differentiation of amino acid derivatives with achiral pillar[5]arene homologs
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Complexation of achiral pillar[5]arenes with chiral amines induced strong circular dichroism (CD) signals. The CD responses differed drastically depending on the nature of the amino acid guest, and they significantly varied and part of them even inverted, upon increasing the length of the alkyl chains of the pillar[5]arenes guests. Accordingly, this tactic allowed for the unprecedented simultaneous enantiomeric and structural differentiation of α-amino esters with homologous molecular hosts.
- Ji, Jiecheng,Li, Yizhou,Xiao, Chao,Cheng, Guo,Luo, Kui,Gong, Qiyong,Zhou, Dayang,Chruma, Jason J.,Wu, Wanhua,Yang, Cheng
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supporting information
p. 161 - 164
(2019/12/30)
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- Solvent-free synthesis of pillar[6]arenes
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An efficient solvent-free procedure for the synthesis of pillar[6]arenes has been developed. The procedure involves the solid-state condensation of finely milled 1,4-dialkoxybenzene and paraformaldehyde by grinding in the presence of a catalytic amount of H2SO4. The use of organic solvents for the extraction of products has also been avoided. Operational simplicity, compatibility with various 1,4-dialkoxybenzenes, non-chromatographic purification technique, high yields and mild reaction conditions are the notable advantages of this procedure. A large scale reaction demonstrated the practical applicability of this methodology.
- Santra,Kopchuk,Kovalev,Zyryanov,Majee,Charushin,Chupakhin
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supporting information
p. 423 - 426
(2016/01/30)
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- Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides
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An efficient and practical short-chain alkoxylation of unactivated aryl bromides has been developed with special attention focussed on the applicability of the reaction. Sodium alkoxide is used as the nucleophile, and the corresponding alcohol as the solvent. The reaction requires neither precious metals nor organic ligands. It uses a catalytic system consisting of copper(I) bromide as a catalyst, the corresponding alkyl formate as a noncontaminating cocatalyst, and lithium chloride as an additive. A wide range of substrates and test cases highlight the synthetic utility of the approach. Considering the commercial accessibility and affordability of the feedstocks, this protocol shows promise as a new alternative for the sustainable preparation of aryl alkyl ethers.
- Guo, Ying,Fan, Xue-Min,Nie, Min,Liu, Hong-Wei,Liao, Dao-Hua,Pan, Xian-Dao,Ji, Ya-Fei
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p. 4744 - 4755
(2015/08/03)
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- Tuning the moisture and thermal stability of metal-organic frameworks through incorporation of pendant hydrophobic groups
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An isostructural series of NbO-type porous metal-organic frameworks (MOFs) with different dialkoxy-substituents of formula Cu2(TPTC-OR) (TPTC-OR = 2′,5′-di{alkyl}oxy-[1,1′:4′,1″-terphenyl]-3, 3″,5,5″-tetracarboxylate, R = Me, Et, nPr, nHex) has been synthesized and characterized. The moisture stability of the materials has been evaluated, and a new superhydrophobic porous MOF has been identified. The relationship between pendant side chain length and thermal stability has been analyzed by in situ synchrotron powder X-ray diffraction, showing decreased thermal stability as the side chain length is increased, contradictory to thermogravimetric decomposition studies. Additionally, the four materials exhibit moderate Brunauer-Emmett-Teller (BET) and Langmuir surface areas (1127-1396 m2 g-1 and 1414-1658 m2 g -1) and H2 capacity up to 1.9 wt % at 77 K and 1 bar.
- Makal, Trevor A.,Wang, Xuan,Zhou, Hong-Cai
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p. 4760 - 4768
(2013/12/04)
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- Alkyloxy substituted organic dyes for high voltage dye-sensitized solar cell: Effect of alkyloxy chain length on open-circuit voltage
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Three novel organic dyes (SB1, SB2, and SB3) containing 4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline as electron donor and cyanoacrylic acid as electron acceptor bridged by alkyloxy (methyl = SB1, propyl = SB2 and hexyl = SB3) substituted p-phenylenevinylene linkers have been synthesized. Density functional theory (DFT) has employed to study electron distribution and intramolecular charge transfer. Increase in alkyl chain length in alkyloxy substituent leads to increase in open-circuit voltage (V OC), which is found to be related to the increased electron lifetime at open-circuit condition. Under AM 1.5 G 1 sun light illumination (100 mW/cm2), an optimized SB3-sensitized cell show a short-circuit photocurrent density (JSC) of 12.83 mA/cm2, an open-circuit voltage (VOC) of 0.745 V and a fill factor (FF) of 0.64, corresponding to an overall conversion efficiency (η) of 6.12%. Little degradation in η observed over 40 days is indicative of long-term stability of the SB-series dyes.
- Ko, Soo-Byung,Cho, An-Na,Kim, Mi-Jeong,Lee, Chang-Ryul,Park, Nam-Gyu
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experimental part
p. 88 - 98
(2012/04/04)
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- METHODS AND COMPOSITIONS FOR CONTROL OF GYPSY MOTHS, Lymanria dispar
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The invention provides in part dialkoxybenzene and eugenol compounds for controlling infestation by a Lymantria dispar, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; with the provisos that when R2 is at position 2, R3 if present is at position 3, or when R2 is at to position 3, R3 if present is at positions 2 or 4, or when R2 is at position 4, R3 if present is at position 2; or of Formula II: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; or mixtures thereof.
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Page/Page column 12
(2010/08/07)
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- METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni
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The invention provides in part dialkoxybenzene compounds for controlling infestation by a Trichoplusia ni, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; except that when R2 is at position 2, R3 if present is at position 3, and when R2 is at position 3, R3 if present is at positions 2 or 4, and when R2 is at position 4, R3 if present is at position 2, and when R2 is at position 4 and R3, if present, has reacted with an OH group at position 1 in a Markovnikov sense, then R3 becomes R4, a dihydrofuran.
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Page/Page column 11
(2010/07/04)
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- Screening of dialkoxybenzenes and disubstituted cyclopentene derivatives against the cabbage looper, Trichoplusia ni, for the discovery of new feeding and oviposition deterrents
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The antifeedant, oviposition deterrent, and toxic effects of dialkoxybenzene minilibraries and of disubstituted cyclopentene minilibraries (i.e., consisting of four to five compounds) along with their pure constituent compounds were assessed against third instar larvae and adults of the cabbage looper, Trichoplusia ni, in laboratory bioassays in a search for new insect control agents. These compounds mimic naturally occurring bioactive odorants and tastants and are relatively easily prepared from commodity chemicals. Most of these libraries strongly deterred larval feeding, with some exhibiting strong toxic and oviposition deterrent effects as well. Our results suggest some structure-function relationships within these libraries. Replacement of a methyl group with larger alkyl substituents increased the feeding deterrent effects in most cases. The presence of a free hydroxyl group, irrespective of the carbon framework or alkyl substituent, served to reduce feeding deterrent effects in all series of compounds. Further, exceeding a certain group size also generally had a detrimental effect. This information will be useful in designing new insect control agents for agriculture. Some of these libraries and compounds may have potential for development as commercial insecticides.
- Akhtar, Yasmin,Isman, Murray B.,Paduraru, Peggy M.,Nagabandi, Srinivas,Nair, Ranjeet,Plettner, Erika
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scheme or table
p. 10323 - 10330
(2009/10/02)
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- The synthesis and conformation of oxygenated trianglimine macrocycles
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The synthesis of series of D2h and C2v symmetric oxygenated aromatic dicarboxaldehydes, using dilithiation methodology, is described along with their reactivity in the [3 + 3] cyclocondensation reaction with (1R,2R)-diaminocyclohexane to give oxygenated trianglimine macrocycles. Macrocycles derived from C2v symmetric dialdehydes give macrocycles with a stereogenic aromatic plane with complete diastereocontrol, as a mixture of retainers.
- Kuhnert, Nikolai,Lopez-Periago, Ana,Rossignolo, Giulia M.
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p. 524 - 537
(2007/10/03)
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- Preparation and nonlinear optics of monodisperse oligo(1,4-phenyleneethynylene)s
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Oligo(1,4-phenyleneethynylene)s 1a-e, with solubilizing propoxy side chains, were prepared by use of Hagihara-Sonogashira coupling reactions. The synthetic strategy was based on a building block system and on the use of trimethylsilyl and triisopropylsily
- Meier, Herbert,Ickenroth, Dirk,Stalmach, Ulf,Koynov, Kaloian,Bahtiar, Ayi,Bubeck, Christoph
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p. 4431 - 4443
(2007/10/03)
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- Alkoxylated p-phenylenevinylene oligomers: Synthesis and spectroscopic and electrochemical properties
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Twenty-one n-alkoxy substituted phenylenevinylene oligomers were synthesized, varying in size, number and position of the OR groups. IR,MS and solubility data are presented. NMR measurements provided the molecular structure as well as information about conformations and molecular dynamics. UV and of cyclic voltammetric data give correlations of chemical structure (number and position of OR substituents) with separate HOMO and LUMO energies.
- Ndayikengurukiye, Henri,Jacobs, Sven,Tachelet, Wim,Van Der Looy, Johan,Pollaris, Anne,Geise, Herman J.,Claeys, Magda,Kauffmann, Jean M.,Janietz, Silvia
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p. 13811 - 13828
(2007/10/03)
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- Effects of side arm length and structure of para-substituted phenyl derivatives on their binding to the host cyclobis(paraquat-p-phenylene)
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The binding constants with the host cyclobis(paraquat-p-phenylene), 14+, have been determined in CH3CN by UV-vis spectrophotometry for a series of p-phenylene guests, symmetrically substituted with side arms of varying length and fun
- Castro, René,Nixon, Kendric R.,Evanseck, Jeffrey D.,Kaifer, Angel E.
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p. 7298 - 7303
(2007/10/03)
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- Monodisperse dialkoxy-substituted oligo(phenyleneethenylene)s
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Individual but connected synthetic routes for the preparation of the all-E-configured 2,5-dipropoxy-substituted oligo(1,4-phenyleneethenylene)s 1a-g were developed. An increasing number of conjugated stilbene units from n = 1 to n = 11 led to a convergent bathochromic shift (Δλ = λz - λ1 = 127 nm) in the UV/Vis absorption. An exponential function for the convergence of the absorption energies (wavelengths) in conjugated systems is proposed. By a simple extrapolation of this function the effective chain length may be determined. VCH Verlagsgesellschaft mbH, 1996.
- Stalmach, Ulf,Kolshorn, Heinz,Brehm, Isabella,Meier, Herbert
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p. 1449 - 1456
(2007/10/03)
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- The Electrochemical Metoxylation of Dialkoxyaromatic Compounds and the Determination of Isomer Ratios by N.M.R. Spectroscopy
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Electrolysis in methanol-KOH solution of p-diethoxy-, p-di-n-propoxy-, p-di-isopropoxy-, p-di-n-butoxy-, p-di-isobutoxy-, and p-di-s-butoxy-benzenes afforded the corresponding 3,6-dialkoxy-3,6-dimethoxy-cyclohexa-1,4-diene, shown by 1H n.m.r. spectroscopy to be an approximately equimolar mixture of cis- and trans-isomers.Likewise, from 9,10-diethoxyanthracene was obtained an equimolar mixture of the cis- and trans-isomers of 9,10-diethoxy-9,10-dimethoxy-9,10-dihydroanthracene.
- Elgy, Geraldine M.,Jennings, W. Brian,Pedler, Alan E.
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p. 1255 - 1260
(2007/10/02)
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- PHOSPHORORGANISCHE VERBINDUNGEN 101. TERTIAERE PHOSPHINE MIT ORTHOALKOXYPHENYL-GRUPPEN. Synthese und Eigenschaften
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Alkylphenylethers, ortho-lithiated in good yields, are transformed according to scheme (1) to the triarylphosphines ArPPh2, Ar2PPh and Ar3P (Ar contains in all cases an ortho-alkoxy group) (Table 1.).Hydroquinonedialkylethers can be lithiated twice, forming the compounds 102 and 103.Table 2 summarizes some arylalkylethers (71 - 101) which were lithiated; table 7 presents 12 new arylalkylethers.The syntheses of triarylphosphines with one or two bulky groups (105 - 110) and of triarylphosphines with one or two 3,4-dialkoxyphenyl groups (111 - 114) are reported.The 31P-spectra of the compounds prepared are discussed with respect to the validity of the Tolman-rule.
- Horner, L.,Simons, G.
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p. 189 - 210
(2007/10/02)
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