- Syntheses, derivatives, solubility, and interfacial properties of 2-methyl-2-polyfluoroalkenyloxymethyl-1,3-propanediols: Potential building blocks for syntheses of amphiphatic macromolecules
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2-Hydroxymethyl-2-methyl-1,3-propanediol (A) was reacted with (Me3Si)2NH and toluenesulfonyl chloride (TsCl) to give mainly CH3C(CH2OSiMe3)3 (1), and CH3C(CH2OTs)3 (2), respectively. With allyl bromide, the products were CH3C(CH2OCH2 CH=CH2)2(CH2OH) (3) and CH3C(CH2OCH2CH= CH2)(CH2OH)2·H2O (4). The reactions of 4 with perfluoroalkyl iodides (RfI) were catalyzed by Cu(I)Cl to form 2-methyl-2-polyfluoroalkenyloxymethyl-1,3-propanediols: (RfCH=CHCH2OCH2) C(Me)(CH2OH)2 [Rf = C4F9 (5), C8F17 (6), and (CF2CF2)4OCF(CF3)2 (7)]. Reduction of 5 and 6 with hydrogen gave two new 2-methyl-2-polyfluoroalkyloxymethyl-1,3-propanediols, 8 and 9. The sodium salt of 9 was reacted with allyl bromide or acetyl chloride to form (C8F17CH2 CH2CH2OCH2)C(Me) (CH2OX)(CH2OH)2 [where X = CH2CH=CH2 (10) or C(O)CH3 (12)] and (C8F17 CH2CH2CH2 OCH2)C(Me)(CH2OX)2 [where X = CH2CH=CH2 (11) or C(O)CH3 (13)]. Reaction of tolenesulfonyl chloride with 7 gave the monotosylate, 14, as the sole product. With 4-trifluoromethylbenzyl bromide, the sodium salt of 4 gave (4-CF3C6H4 CH2OCH2)C(Me) (CH2CH=CH2)(CH2OH)·H2O (15). The compounds were characterized by NMR (1H, 13C, 19F, 29Si), GC-MS, and high-resolution MS or elemental analyses. UV evidence was obtained for partitioning of 9, 12, 14, and 15 between perfluorodecalin and n-octanol. The test compounds acted as surfactants by facilitating the solubility of phenol and Si(CH=CH2)4 in perfluorodecalin. The single-crystal X-ray structure of 8 was also obtained. It crystallized in the monoclinic space group P21/c, and unit cell dimensions were α = 24.966(2) A (α = 90°), b = 6.1371(6) A (β = 100.730(2)°), and c = 10.5669(10) A (γ = 90°).
- Omotowa, Bamidele A.,Judd, Matthew R.,Twamley, Brendan,Shreeve, Jean'ne M.
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- NOVEL COMPOUND having VINYLPHENYLOXY moiety AND PHOTOSENSITIVE PHOTORESIST COMPOSITION INCLUDING THE SAME
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The present invention relates to a compound having a vinylphenyloxy group which is represented by chemical formula A, B, or C, and a photosensitive photoresist composition including the same. The chemical formula A, B, or C are as described in the detaile
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Paragraph 0136-0138
(2018/09/12)
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- NOVEL COMPOUND having VINYLPHENYLOXY moiety AND PHOTOSENSITIVE PHOTORESIST COMPOSITION INCLUDING THE SAME
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The present invention relates to a compound having a vinylphenyloxy group which is represented by chemical formula A, B, or C, and a photosensitive photoresist composition including the same. The chemical formula A, B, or C are as described in the detaile
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Paragraph 0136-0138
(2018/09/20)
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- Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized tripodal molecular switch as a highly selective sequential pH sensor in aqueous solution
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The development and photophysical properties of a biomimetic analogue of microbial siderophore from quinolobactin have been described. The putative analogue, 5,5′-(2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)-bis(azanediyl)-bis(methylene)diquinolin-8-ol (TAME5OX), was synthesized with three bidentate 8-hydroxyquinoline (8HQ) groups, connected to a 1,1,1-tris(aminomethyl)ethane framework, and was selected for its potential applications in chemical and biological fields. A combination of absorption and emission spectrophotometry, potentiometry, electrospray mass spectrometry, NMR, IR and theoretical investigation was used to fully characterize TAME5OX. The intense fluorescence from TAME5OX is quenched intermittently under acidic and basic conditions due to the photoinduced intramolecular electron transfer from excited N-pyridyl to hydroxyl moiety of 8HQ units. This renders the ligand an OFF-ON-OFF type of pH-dependent fluorescent sensor. DFT was employed for optimization and evaluation of vibrational modes, excitation and emission properties of the protonated, neutral, deprotonated states of the analogue. Anomalous enhancement observed in the fluorescence spectra of the neutral form of the sensor can be attributed to subtle structural differences from its cationic and anionic forms. Plausible explanations for low fluorescence of the acidic as well as basic form are provided. This journal is
- Akbar, Rifat,Baral, Minati,Kanungo
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p. 16207 - 16222
(2015/03/04)
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- Sweet switches: Azobenzene glycoconjugates synthesized by click chemistry
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Azobenzene glycoconjugates can be switched between two isomeric states, E and Z, to change the spatial orientation of the conjugated carbohydrate ligands. Mono-, di- and trivalent azobenzene glycoconjugates were synthesized using click chemistry and their
- Chandrasekaran, Vijayanand,Lindhorst, Thisbe K.
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supporting information; experimental part
p. 7519 - 7521
(2012/10/07)
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- 2,6,7-Trithiabicyclo[2.2.2]octanes as promising photolabile tags for combinatorial encoding
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(Chemical Equation Presented) The adducts of trithiabicyclo[2.2.2]octane (TTBO) and carbonyl compounds undergo efficient photoinduced fragmentation with quantum yields comparable to that of dithiane adducts. The effect of the third sulfur on the stability of the respective radical cations and radicals is examined computationally and experimentally in a laser flash photolysis study. A straightforward synthetic approach to a variety of 4-substituted trithiabicyclo[2.2.2]octanes from 3-bromo-2,2-bis-(bromomethyl)propanol is developed, making a diverse set of mass-differentiated photolabile tags readily available for combinatorial encoding.
- Valiulin, Roman A.,Kutateladze, Andrei G.
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p. 335 - 338
(2008/09/17)
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- A new tripodal ligand system based on the iminophosphorane functional group. Part 1: Synthesis and characterization
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Two tripodal alcohols, viz., 1,1,1-tris(hydroxymethyl)ethane and α,α,α-tris(hydroxymethyl)toluene were converted by an efficient multi-step pathway involving azide formation into the corresponding tris(iminophosphorane) scaffolds bearing cyclopentyl (Cp)
- Beaufort, Laurence,Delaude, Lionel,Noels, Alfred F.
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p. 7003 - 7008
(2008/02/05)
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- Syntheses of a series of S6 thioether cages and their coordination chemistry with Ag+
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The syntheses of four S6-cages with different cavity sizes are described. In regard of potential applications for radioimmunotherapy with 111Ag, their coordination behaviour towards Ag(I) was evaluated by studies of their reactivity
- Alberto, Roger,Angst, Daniela,Ortner, Kirstin,Abram, Ulrich,Schubiger, P. August,Kaden, Thomas A.
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p. 409 - 417
(2008/02/10)
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- Reactivity of Neopentyl-Like Compounds in the Synthesis of Branched Polyethers
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Two singly branched symmetrical hexaethers have been synthesized, starting from 2-bromomethyl-2-methyl-1,3-dibromopropane, in a surprisingly efficient one-pot nucleophilic substitution reaction.It is proposed that the expected adverse neopentyl effect is compensated by favourable neighbouring-group participation involving a 'bromonium'-like four-membered-ring transition state.The corresponding trichloride also reacted cleanly, although much more slowly, while the tritosylate gave an oxetane derivative.
- Dale, Johannes,Fredriksen, Siw B.
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p. 278 - 282
(2007/10/02)
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