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Supramolecular functionalized polybenzoxazines from azobenzene carboxylic acid/azobenzene pyridine complexes: synthesis, surface properties, and specific interactions
(2015-01-01)
Mohamed, Mohamed Gamal
;
Hsiao, Chi-Hui
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Hsu, Kuo-Chih
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Lu, Fang-Hsien
;
Shih, His-Kang
In this study we synthesized Azo-COOH BZ, a new benzoxazine derivative containing both azobenzene and carboxylic acid units, through the reaction of 4-(4-hydroxphenylazo) benzoic acid (Azo-COOH, itself prepared through a diazonium reaction of 4-aminobenzoic acid with phenol in the presence sodium nitrite and NaOH) with paraformaldehyde and aniline in 1,4-dioxane. Fourier transform infrared (FTIR) spectroscopy and H-1 and C-13 nuclear magnetic resonance spectroscopy confirmed the chemical structure of Azo-COOH BZ. We used differential scanning calorimetry (DSC), thermogravimetric analysis, and FTIR spectroscopy to investigate the curing behavior of this new benzoxazine monomer. DSC revealed that the exothermic peak representing the ring opening polymerization of the benzoxazine unit appeared at low temperature relative to those of typical benzoxazines, indicating the presence of the carboxylic acid and azobenzene units of this monomer catalyzing the benzoxazine ring opening reaction. In addition, blending with various molar ratios of a benzoxazine monomer presenting a pyridyl unit (Azopy BZ) led to strong intermolecular hydrogen bonding between the CO2H group of Azo-COOH BZ and the pyridyl group of Azopy BZ. These supramolecular complex systems also featured significantly lower curing temperatures (down from ca. 200 degrees C of Azo-COOH BZ to 150 degrees C of supramolecular complex), with their products retaining the high water contact angles required for low-surface-energy applications.
Bio-Inspired Supramolecular Chemistry Provides Highly Concentrated Dispersions of Carbon Nanotubes in Polythiophene
(2016-06-01)
Lin, Yen-Ting
;
Singh, Ranjodh
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Kuo, Shiao-Wei
;
Ko, Fu-Hsiang
;
材料科學與工程學系
In this paper we report the first observation, through X-ray diffraction, of noncovalent uracil-uracil (U-U) dimeric 7r-stacking interactions in carbon nanotube (CNT)-based supramolecular assemblies. The directionally oriented morphology determined using atomic force microscopy revealed highly organized behavior through pi-stacking of U moieties in a U-functionalized CNT derivative (CNT-U). We developed a dispersion system to investigate the bio-inspired interactions between an adenine (A)-terminated poly(3-adeninehexyl thiophene) (PAT) and CNT-U. These hybrid CNT-U/PAT materials interacted through pi-stacking and multiple hydrogen bonding between the U moieties of CNT-U and the A moieties of PAT. Most importantly, the U center dot center dot center dot A multiple hydrogen bonding interactions between CNT-U and PAT enhanced the dispersion of CNT-U in a high-polarity solvent (DMSO). The morphology of these hybrids, determined using transmission electron microscopy, featured grape-like PAT bundles wrapped around the CNT-U surface; this tight connection was responsible for the enhanced dispersion of CNT-U in DMSO.
Photo-Crosslinking of Pendent Uracil Units Provides Supramolecular Hole Injection/Transport Conducting Polymers for Highly Efficient Light-Emitting Diodes
(2015-05-01)
Shih, Hsi-Kang
;
Chen, Yi-Han
;
Chu, Yu-Lin
;
Cheng, Chih-Chia
;
Chang, Feng-Chih
A new process for modifying a polymeric material for use as a hole injection transport layer in organic light-emitting diodes has been studied, which is through 2 + 2 photodimerization of a DNA-mimetic -conjugated poly(triphenylamine-carbazole) presenting pendent uracil groups (PTC-U) under 1 h of UV irradiation. Multilayer florescence OLED (Organic light-emitting diodes) device with the PTC-U-1hr as a hole injection/transport layer (ITO (Indium tin oxide)/HITL (hole-injection/transport layer) (15 nm)/N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) (15 nm)/Tris-(8-hydroxyquinoline)aluminum (Alq(3)) (60 nm)/LiF (1 nm)/Al (100 nm)) is fabricated, a remarkable improvement in performance (Q(max) (external quantum efficiency) = 2.65%, B-max (maximum brightness) = 56,704 cd/m(2), and LE (luminance efficiency)(max) = 8.9 cd/A) relative to the control PTC-U (Q(max) = 2.40%, B-max = 40,490 cd/m(2), and LEmax = 8.0 cd/A). Multilayer phosphorescence OLED device with the PTC-U-1hr as a hole injection/transport layer (ITO/HITL (15 nm)/Ir(ppy)(3):PVK (40 nm)/BCP (10nm)/Alq(3) (40 nm)/LiF (1 nm)/Al (100 nm)) is fabricated by successive spin-coating processes, a remarkable improvement in performance (Q(max) = 9.68%, B-max = 41,466 cd/m(2), and LEmax = 36.6 cd/A) relative to the control PTC-U (Q(max) = 8.35%, B-max = 34,978 cd/m(2), and LEmax = 30.8 cd/A) and the commercial product (poly(3,4-ethylenedioxythiophene):polystyrenesulfonate) PEDOT:PSS (Q(max) = 4.29%, B-max = 15,678 cd/m(2), and LEmax = 16.2 cd/A) has been achieved.
A facile cosolvent/chelation method for the preparation of semi-crystalline CuCl2(ethylene glycol)/poly(3-hexylthiophene) complexes displaying specific luminescence properties
(2015-01-01)
Lu, Fang-Hsien
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Mohamed, Mohamed Gamal
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Liu, Tzeng-Feng
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Chao, Chuen-Guang
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Kuo, Shiao-Wei
Semi-crystalline CuCl2(ethylene glycol)/poly(3-hexylthiophene) complexes (CE-P3HT) with specific textures and self-assembled structures can be fabricated using a facile co-solvent/chelation method. The morphologies and self-assembled structures of these CE-P3HT complexes were dependent on the concentration of CuCl2(ethylene glycol) (CuCl(2)EG) in solution. Transmission electron microscopy (TEM) revealed the CE-P3HT sample comprising EG and numerous CuCl2/P3HT dots (C-P3HT dots) that originated from the P3HT main chains interacting with CuCl2 crystals; the average size of this C-P3HT dots was ca. 20 nm. Prior to formation of the solid state of CE-P3HT structures, the CE-P3HT complex in solution displayed a novel phenomenon: a specific luminescence property with an absorption energy gap of 3.71-4.46 eV. This quantum effect resulted from the chelates formed between the Cu2+ ions and the thioether units of the conjugated P3HT polymer.
Unusual Emission of Polystyrene-Based Alternating Copolymers Incorporating Aminobutyl Maleimide Fluorophore-Containing Polyhedral Oligomeric Silsesquioxane Nanoparticles
(2017-03-01)
Mohamed, Mohamed Gamal
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Jheng, Yu-Ru
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Yeh, Shu-Ling
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Chen, Tao
;
Kuo, Shiao-Wei
In this study, we synthesized an unusual 2-aminobutyl maleimide isobutyl polyhedral oligomeric silsesquioxane (MIPOSS-NHBu) monomer lacking conventional fluorescent groups. We then prepared poly(styrene-alt-2-aminobutyl maleimide isobutyl POSS) [poly(S-alt-MIPOSS-NHBu)] and poly(4-acetoxystyrene-alt-2-aminobutyl maleimide isobutyl POSS) [poly(AS-alt-MIPOSS-NHBu)] copolymers through facile free radical copolymerizations using azobisisobutyronitrile as the initiator and tetrahydrofuran as the solvent. A poly(4-hydroxystyrene-alt-2-aminobutyl maleimide isobutyl POSS) [poly(HS-alt-MIPOSS-NHBu)] copolymer was prepared through acetoxyl hydrazinolysis of poly(AS-alt-MIPOSS-NHBu). We employed H-1, C-13, and Si-29 nuclear magnetic resonance spectroscopy; Fourier transform infrared spectroscopy; differential scanning calorimetry; and photoluminescence spectroscopy to investigate the structures and the thermal and optical properties of the monomers and novel POSS-containing alternating copolymers. Intramolecular hydrogen bonding between the amino and dihydrofuran-2,5-dione group and clustering of the locked C = O groups from the POSS nanoparticles in the MIPOSS-NHBu units restricted the intramolecular motion of the polymer chain, causing it to exhibit strong light emission. As a result, the MIPOSS-NHBu monomer and the poly(AS-alt-MIPOSS-NHBu) copolymer both have potential applicability in the detection of metal ions with good selectivity.
A quenching method for the preparation of metal oxide-polythiophene composites having fiber structures
(2014-01-01)
Lu, Fang-Hsien
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Mohamed, Mohamed-Gamal
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Liu, Tzeng-Feng
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Chao, Chuen-Guang
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Dai, Lizong
In this study we developed a simple quenching method to fabricate metal oxide (CuO, ZnO, TiO2, Fe(OH) 3)polythiophene (PT) composites. By varying the metal oxide, PT, and rate of crystallization, we could control the fiber morphology in these composites. Four-probe-station analyses revealed that the conductivities of these metal oxide-PT composites ranged from 10(-5) to 10(-3) S cm(-1), higher than that of any species of metal oxide alone (from 10(-10) to 10(-7) S cm(-1)), because the fiber morphology behaved as an exceptional transmission factor for electrons. Moreover, these metal oxide-PT composites exhibited the characteristics of colloids, as well as high viscosity, suggesting that they could also be applied as coatings on silicon and glass substrates, and could provide the opportunity to form useful materials for large-scale gas sensors due to good flexibility and porosity. UV-vis spectroscopic analyses revealed variations in the energy level (>3.37 eV for ZnO) and confirmed the mechanism of the morphology change of the composite.
Hydrogen Bond-Mediated Self-Assembly of Polyhedral Oligomeric Silsesquioxane-Based Supramolecules
(2010-08-05)
Shih, Ruey-Sheng
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Lu, Chu-Hua
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Kuo, Shiao-Wei
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Chang, Feng-Chih
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應用化學系
In this study, a functionalized pentaerythritol star polyester compound [tetrakis(nicotinoxymethyl)methane, TNMM] and an octakis[dimethyl(4-hydroxyphenethyl)siloxy]silsesquioxane (OP-POSS) were synthesized and used as tetrahedral and cubic building blocks, respectively, for three-dimensional, hydrogen-bond-mediated, polyhedral oligomeric silsesquioxane- (POSS-) based supramolecular network structures. With noncovalent chain extension of hydrogen bonds between its pyridine and phenol groups, the PUSS-based supramolecular networks exhibited thermally reversible properties. Compared with the glass transition temperature of OP-POSS (ca. 20 degrees C) and the melting temperature of TNMM (ca. 70 degrees C), the hydrogen-bond-mediated miscible blend of 40 wt % TNMM in OP-POSS exhibited a single and higher glass transition temperature (37 degrees C). Because of its strong intermolecular hydrogen bonding, the dewetting pattern of the blend of 40 wt % TNMM in OP-POSS formed ringlike structures rather than the droplets formed by pure OP-POSS. A transparent, brittle, and glassy solid at room temperature, the blend of 40 wt % TNMM in OP-POSS is an explicit and successful example of a PUSS-based hydrogen-bonded supramolecular network.
Self-assembly of an A-B diblock copolymer blended with a C homopolymer and a C-D diblock copolymer through hydrogen bonding interaction
(2010-08-19)
Chen, Wan-Chun
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Kuo, Shiao-Wei
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Chang, Feng-Chih
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應用化學系
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Department of Applied Chemistry
In this study, we investigated the miscibility, phase behavior, and self-assembled nanostructures formed from the immiscible crystalline-amorphous diblock copolymer poly(epsilon-caprolactone-b-4-vinyl pyridine) (PCL-b-P4VP, A-B) when blended with the homopolymer poly(vinyl phenol) (PVPh, C) and the diblock copolymer poly(vinyl phenol-b-styrene) (PVPh-b-PS, C-D). Long-range-ordered microphase separation was difficult to achieve in the PCL-b-P4VP/PVPh (A-B/C) blend system because PVPh interacted with both the P4VP and PCL blocks simultaneously through hydrogen bonding interactions. In contrast, we observed sharp, multiple orders of diffraction in the SAXS profiles of the PCL-b-P4VP/PVPh-b-PS (A-B/C D) blend system, indicating that perfect microphase separation occurred because the incorporation of the PS block induced the PVPh block to hydrogen bond preferentially with the P4VP block. This simple A-B/C-D (PCL-b-P4VP/PVPh-b-PS) diblock copolymer mixture exhibited self-assembly behavior (a three-lamella phase) similar to that of a corresponding ABC triblock copolymer. (C) 2010 Elsevier Ltd. All rights reserved.
Hybridization sensing by electrical enhancement with nanoparticles in nanogap
(2008-11-01)
Chen, Chun-Chi
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Ko, Fu-Hsiang
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Chang, Edward Yi
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Chang, Feng-Chih
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Kuo, Shiao-Wei
In this work, the monolayer of gold nanoparticles within 72 nm gap has been proposed to function as a DNA sensor. The authors suggest that the nanoparticles in the nanogap could act as hopping sites which amplify the conductance of hybridized DNA strands. The conductance amplification between single strand and hybridized DNAs through gold nanoparticles is observed. Various concentrations of capture and target DNA are discussed for optimal hybridization sensing purpose. With the help of 1 nM capture DNAs, this sensor is able to analyze target DNA sequences at very low concentration of 1 fM. Furthermore, by means of adjusting the denature temperature to 60 degrees C, even single mismatch hybridization could be discriminated.
Thermal and mechanical properties of microcellular thermoplastic SBS/PS/SBR blend: effect of crosslinking
(2011-02-03)
Shih, Ruey-Sheng
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Kuo, Shiao-Wei
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Chang, Feng-Chih
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應用化學系
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Department of Applied Chemistry
This study investigates the effect of peroxide crosslinking on the structure and mechanical properties for SBS/PS/SBR foams composed of polystyrene (PS), poly(styrene-b-butadiene) diblock copolymer (SBR-1502), and poly(styrene-b-butadiene-b-styrene) triblock copolymer (SBS). The cell size and its distribution of SBS/PS/SBR foams were investigated by SEM images, showing the smaller and denser of hollow cells for the SBS/PS/SBR foam containing the higher concentration of DCP (dicumyl peroxide). As expected, the density of the SBS/PS/SBR foams increases with increasing the content of DCP. The high density of polymeric foams exhibits the high mechanical properties such as hardness, shrinkage, tensile strength, tear strength, elongation at break, and compression set. (C) 2010 Elsevier Ltd. All rights reserved.

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