Design, synthesis, and imaging study of a photoactive polymer containing aryl substituted diazoketo groups

Liu, Lu; Zou, Yingquan

doi:10.1002/app.34512

Cited by 6 publications

(6 citation statements)

References 27 publications

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“…Benzoylacetic acid was prepared according to the literature procedure . To a solution of acetophenone (12 g, 0.10 mol), dry tetrahydrofuran (50 mL) in 250 mL overnight-oven-dried round-bottomed flask, NaH (60%) in oil (10.5 g, 0.25 mol) and dimethylcarbonate (16.2 g, 0.18 mol) was added.…”

Section: Methodsmentioning

confidence: 99%

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Catalytic Promiscuity of Ancestral Esterases and Hydroxynitrile Lyases

et al. 2016

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Catalytic promiscuity is a useful, but accidental, enzyme property, so finding catalytically promiscuous enzymes in nature is inefficient. Some ancestral enzymes were branch points in the evolution of new enzymes and are hypothesized to have been promiscuous. To test the hypothesis that ancestral enzymes were more promiscuous than their modern descendants, we reconstructed ancestral enzymes at four branch points in the divergence hydroxynitrile lyases (HNL’s) from esterases ~100 million years ago. Both enzyme types are α/β-hydrolase-fold enzymes and have the same catalytic triad, but differ in reaction type and mechanism. Esterases catalyze hydrolysis via an acyl enzyme intermediate, while lyases catalyze an elimination without an intermediate. Screening ancestral enzymes and their modern descendants with six esterase substrates and six lyase substrates found higher catalytic promiscuity among the ancestral enzymes (P <0.01). Ancestral esterases were more likely to catalyze a lyase reaction than modern esterases and the ancestral HNL was more likely to catalyze ester hydrolysis than modern HNL’s. One ancestral enzyme (HNL1) along the path from esterase to hydroxynitrile lyases was especially promiscuous and catalyzed both hydrolysis and lyase reactions with many substrates. A broader screen tested mechanistically related reactions that were not selected for by evolution: decarboxylation, Michael addition, γ-lactam hydrolysis and 1,5-diketone hydrolysis. The ancestral enzymes were more promiscuous than their modern descendants (P = 0.04). Thus, these reconstructed ancestral enzyme are catalytically promiscuous, but HNL1 is especially so.

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Section: Methodsmentioning

confidence: 99%

“…32 To a solution of acetophenone (12 g, 0.10 mol), dry tetrahydrofuran (50 mL) in 250 mL overnight-oven-dried round-bottomed flask, NaH (60%) in oil (10.5 g, 0.25 mol) and dimethylcarbonate (16.2 g, 0.18 mol) was added. The suspension was heated to reflux for 2 h and cooled to room temperature.…”

Section: Ancestral Enzyme Reconstructionmentioning

confidence: 99%

Catalytic Promiscuity of Ancestral Esterases and Hydroxynitrile Lyases

et al. 2016

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“…23 During the past decade, there were several excellent works demonstrating some polyimide and polymethacrylate systems, including o-NB group could be used as positive photoresist. [24][25][26][27][28][29] O-NB groups were used as photolabile-protecting groups for carboxyl acids UV irradiation, so that the photoresist resins could be etched alone without photoacid generators. These V C 2014 Wiley Periodicals, Inc. polymer resins were synthesized by using polycondensation, 24 free radical polymerization 25 , and atom transfer radical polymerization (ATRP) methods.…”

Section: Introductionmentioning

confidence: 99%

“…[24][25][26][27][28][29] O-NB groups were used as photolabile-protecting groups for carboxyl acids UV irradiation, so that the photoresist resins could be etched alone without photoacid generators. These V C 2014 Wiley Periodicals, Inc. polymer resins were synthesized by using polycondensation, 24 free radical polymerization 25 , and atom transfer radical polymerization (ATRP) methods. [26][27][28][29][30] Moreover, these photoresists were mainly applied in the fields of protein immobilization and incorporated very expensive monomers such as ethyleneglycol methacrylate 26 and fluoromethacylate.…”

Section: Introductionmentioning

confidence: 99%

“…Another example adopted o ‐NB ether in the main chain of polyethers and suggested these materials for positive‐type photoresists . During the past decade, there were several excellent works demonstrating some polyimide and polymethacrylate systems, including o ‐NB group could be used as positive photoresist . O ‐NB groups were used as photolabile‐protecting groups for carboxyl acids UV irradiation, so that the photoresist resins could be etched alone without photoacid generators.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, and photosensitive performance of polymethacrylate‐positive photoresist‐bearing o‐nitrobenzyl group

Guan

Zhao

et al. 2014

J of Applied Polymer Sci

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Novel polymethacrylate‐positive photoresist‐bearing o‐nitrobenzyl group was described herein. The matrix polymer (PCHIBNB) was synthesized by copolymerization of cyclohexyl methacrylate (CHMA), isobornyl methacrylate (IBMA), and o‐nitrobenzyl methacrylate (NBMA) via reversible addition fragmentation chain transfer (RAFT) polymerization method. After UV irradiation, the o‐nitrobenzyl groups of PCHIBNB were photocleaved and the resulting carboxyl groups were highly alkali‐soluble, so that the matrix polymer could be etched by mild alkali solution with no requirements of photosensitizers or photoacid generators. PCHIBNB was characterized by Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H‐NMR) spectroscopy, and gel permeation chromatography (GPC). The photocleavable behaviors of PCHIBNB were determined by FTIR, 1H‐NMR, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC) analysis. The resist formulated with this polymer and cast in tetrahydrofuran (THF) solution showed 10 μm × 10 μm square pattern using a mercury–xenon lamp in a contact printing mode and tetramethyl‐ammonium hydroxide aqueous solution as a developer. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41733.

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Synthesis and characterization of N‐methyl‐2,6‐dinitrodiphenylamine‐4‐diazonium salt and its diazoresin

Wang

Zou

2012

J of Applied Polymer Sci

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A new photosensitive agent, dinitro derivatives of diphenylamine diazonium salt (N-methyl-2,6-dinitrodiphenylamine-4diazonium salt, MDNDDS), and its diazoresin were synthesized. Their photoreactivities and thermostabilities were investigated. Our results revealed that MDNDDS and MDNDDS-resin exhibited greatly improved thermostability both in solid state and in coating film comparing with the conventional unsubstituted and mononitro substituted diphenylamine diazonium salts (DDS and MNDDS, respectively) and their diazoresins. The photosensitivity of MDNDDS was found to be slightly lower than DDS but still comparable with MNDDS. As a result of its improved thermostability, both MDNDDS-resin as a photosensitive agent and lithographic printing plate prepared by MDNDDS-resin will have a long shelf-life, which is very important to reduce waste and factory running-cost. MDNDDS also has a maximum absorption wavelength (k max ) at 425 nm, which means that an iodine gallium lamp (main emission wavelength k em ¼ 420 nm), is better than conventional mercury lamp (k em ¼ 360 nm), to be used as the irradiation source in the photoimaging process. Compared with the mercury lamp, iodine gallium lamp is cheaper and greener. EXPERIMENTAL Materials 4-Chlorobenzoic acid, N-methylaniline were purchased from Alfa Aesar (Tianjin, China). Sulfuric acid, 20% oleum, acetic V C 2012 Wiley Periodicals, Inc.4850

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Design, synthesis, and imaging study of a photoactive polymer containing aryl substituted diazoketo groups

Cited by 6 publications

References 27 publications

Catalytic Promiscuity of Ancestral Esterases and Hydroxynitrile Lyases

Catalytic Promiscuity of Ancestral Esterases and Hydroxynitrile Lyases

Design, synthesis, and photosensitive performance of polymethacrylate‐positive photoresist‐bearing o‐nitrobenzyl group

Synthesis and characterization of N‐methyl‐2,6‐dinitrodiphenylamine‐4‐diazonium salt and its diazoresin

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