Browsing by Author "Chuang, Shih-Ching"

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1-(3-Methoxycarbonyl)propyl-2-selenyl-[6,6]-methanofullerene as a n-Type Material for Organic Solar Cells
(2011-07-01)
Chuang, Shih-Ching
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Chiu, Chih-Wei
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Chien, Shang-Chieh
;
Chu, Chih-Wei
;
Chen, Fang-Chung
Demand for green and renewable energy is stimulating research into future materials for energy production. Thin films of materials possessing both electron accepting and donating functions play a unique role in solar energy technology because of their lightweight, flexibility, and economical, low-temperature, and large-area fabrication. A [60]fullerene derivative,[6,6]-2-selenyl-C(61)-butyric acid methyl ester (SeCBM), has been synthesized in three steps, namely through Friedel-Crafts acylation of selenophene, hydrazone formation and Bamford-Steven reaction. Organic photovoltaic device incorporating SeCBM and the conducting polymer P3HT exhibited an average power conversion efficiency of 3.26% and a champion efficiency as high as 3.81% under AM 1.5G irradiation. (C) 2011 Elsevier B.V. All rights reserved.
[3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem alpha(delta ')-Michael Additions
(2012-05-01)
Chuang, Shih-Ching
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Deng, Jie-Cheng
;
Chan, Fu-Wei
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Chen, Sheng-Yuan
;
Huang, Wei-Je
Organophosphanes promote the [3+2] cycloaddition reactions of dialkyl (E)-hex-2-en-4-ynedioates and [60]fullerene, giving a series of cyclopenteno-fullerenes 3ak bearing phosphorus ylides. This cycloaddition reaction is initiated by the attack of nucleophilic phosphanes at the a(d')-C atom of the dialkyl (E)-hex-2-en-4-ynedioate, which generates a 1,3-dipolar species. These 1,3-dipoles then react with C60 followed by intramolecular cyclization to give cyclopenteno-fullerenes in moderate-to-good yields. In a cyclic voltmmetry study, these novel fullerenes show a larger cathodic shift in their first reduction potential relative to [6,6]phenyl-C61 methyl butyrate, which indicates that these new derivatives possess higher LUMO energy levels.
Access to oxindoles, isatins, and isoxazolinones via multicomponent reactions and facile 6 pi electrocyclization
(2015-08-16)
Chuang, Shih-Ching
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Deng, Jie-Cheng
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應用化學系
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Department of Applied Chemistry
alpha(delta ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of alpha,beta-Dehydroamino Acid Derivatives
(2013-03-01)
Chavan, Arjun S.
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Deng, Jie-Cheng
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Chuang, Shih-Ching
;
應用化學系
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Department of Applied Chemistry
The direct nucleophilic addition of alkyl amines to the alpha(delta')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate alpha,beta-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the alpha-selective nucleophilic conjugate addition to conjugated dimethyl (E)-hex-2-en-4-ynedioate. The reaction with primary alkyl amines gives only the (2E,4E)-stereoisomer, while that with secondary alkyl amines gives the (2E,4E) and (2Z,4E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.
Annulation of Benzamides with [60]Fullerene through Palladium(II)-Catalyzed C-H Bond Activation
(2011-03-18)
Chuang, Shih-Ching
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Rajeshkumar, Venkatachalam
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Cheng, Chun-An
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Deng, Jie-Cheng
;
Wang, Guan-Wu
Palladium-catalyzed heteroannulation of N-substituted benzamides with [60]fullerene, which proceeds through direct sp(2) C-H bond activation to form 7-membered ring pallada-intermediate with C(60), led to formation of [60]fulleroisoquinolinones in moderate to good yields (8-64% based on recovered C(60)). A plausible reaction pathway is proposed.
Assembly of Dimethyl Acetylenedicarboxylate and Phosphanes with Aldehydes Leading to gamma-Lactones Bearing alpha-Phosphorus Ylides as Wittig Reagents
(2012-10-01)
Deng, Jie-Cheng
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Chan, Fu-Wei
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Kuo, Chih-Wei
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Cheng, Chun-An
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Huang, Chien-Yu
We report herein a convenient route to the synthesis of aryl-substituted ?-lactones bearing an a-phosphorus ylide moiety through the assembly of dimethyl acetylenedicarboxylate (DMAD), electron-deficient aldehydes, and triaryl- or trialkylphosphanes in moderate to good yields. The formation of ?-lactones is highly dependent on the reaction time, the phosphane nucleophile, and the molar ratio of DMAD, aldehyde, and phosphane. We found that reactions with a DMAD/aldehyde/tri-p-tolylphosphane molar ratio of 3:1:6 and more electron-deficient aldehydes, such as 4-nitrobenzaldehyde and 4-chloro-3-nitrobenzaldehyde, gave good yields. The isolated ylides reacted with aldehydes as Wittig reagents to give olefins in moderate yields.
Cascade One-Pot Synthesis of Orange-Red-Fluorescent Polycyclic Cinnolino[2,3-f]phenanthridin-9-ium Salts by Palladium(II)-Catalyzed C-H Bond Activation of 2-Azobiaryl Compounds and Alkenes
(1970-01-01)
Jayakumar, Jayachandran
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Vedarethinam, Guganchandar
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Hsiao, Huan-Chang
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Sun, Shang-You
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Chuang, Shih-Ching
Quaternary ammonium salts were synthesized in moderate to good yields through double oxidative C-H bond activation on azobenzenes. The mechanism of the highly regioselective reaction of 2-azobiaryls with alkenes to give orange-red-fluorescent cinnolino[2,3-f]phenanthridin-9-ium salts and 15H-cinnolino[2,3-f]phenanthridin-9-ium-10-ide is proposed to involve ortho C-H olefination of the 2-azobiaryl compound with the alkene, intramolecular aza-Michael addition, concerted metalation-deprotonation (CMD), reductive elimination, and oxidation.
Cascade One-Pot Synthesis of Orange-Red-Fluorescent Polycyclic Cinnolino[2,3-f]phenanthridin-9-ium Salts by Palladium(II)-Catalyzed C-H Bond Activation of 2-Azobiaryl Compounds and Alkenes
(2020-01-07)
Jayakumar, Jayachandran
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Vedarethinam, Guganchandar
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Hsiao, Huan-Chang
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Sun, Shang-You
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Chuang, Shih-Ching
Quaternary ammonium salts were synthesized in moderate to good yields through double oxidative C-H bond activation on azobenzenes. The mechanism of the highly regioselective reaction of 2-azobiaryls with alkenes to give orange-red-fluorescent cinnolino[2,3-f]phenanthridin-9-ium salts and 15H-cinnolino[2,3-f]phenanthridin-9-ium-10-ide is proposed to involve ortho C-H olefination of the 2-azobiaryl compound with the alkene, intramolecular aza-Michael addition, concerted metalation-deprotonation (CMD), reductive elimination, and oxidation.
Chemo-, Regio- and Stereoselective Tricyclohexylphosphine-Catalyzed [3+2] Cycloaddition of Enynes with [60]Fullerene Initiated by 1,4-Michael Addition: Synthesis of Cyclopenteno[60]fullerenes and their Electrochemical Properties
(2013-08-12)
Tseng, Po-Yen
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
Herein we demonstrate a tricyclohexylphosphine-catalyzed cycloaddition of (E)- or (Z)-alkyl 5-substituted phenylpent-2-en-4-ynoates with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo- and regioselective 1,4-addition of phosphines at the -carbon of the enyne substrates. The nucleophilic addition pattern of P(cHx)(3) is found to be different from that of Gilman or Grignard reagents toward the studied enynes. The resulting cyclopentenofullerenes, characterized with spectrometric methods and single crystal X-ray diffraction analysis, exhibit comparable or higher LUMO energy levels than a typical n-type material, [6,6]-phenyl-C-61-butyric acid methyl ester (PCBM).
Effects of the additives n-propylammonium or n-butylammonium iodide on the performance of perovskite solar cells
(2017-01-01)
Hsieh, Cheng-Ming
;
Yu, Yen-Lin
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Chen, Chih-Ping
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Chuang, Shih-Ching
;
應用化學系
Organic-inorganic lead halide perovskite solar cells (PSCs) offer a promising low-cost manufactural solar technology as they are compatible with large-scale and low-temperature (< 100 degrees C) solution processes. Through the optimization of perovskite active layer and phenyl-C-61-butyric acid methyl ester (PC61BM) layer thickness, the normal cells showed 9.7% power conversion efficiency (PCE). Compared with the corresponding normal devices, we observed an improvement in PCE from 9.7% to 11.3% and 10.2% for the devices prepared using 1 vol% of C3H7NH3I and 1 vol% of C4H9NH3I as additives, respectively. Via analysis by ultraviolet-visible (UV-vis) spectroscopy, grazing incidence wide angle X-ray diffraction (GIWAXS), and field emission scanning electron microscopy (FE-SEM), we concluded that the morphological changes, absorption, and crystallinity of the perovskite films played an important role that influenced the performance of the PSC devices with various additives. The presence of 1% of C3H7NH3I or 1% of C4H9NH3I caused the CH3NH3PbI3-x Clx films to grow uniformly with high coverage and continuous phase, as well as with higher absorption; this enabled the corresponding devices to display improved performance.
Evolution of Late Transition-Metal-Catalyzed Intermolecular Reductive Coupling Reaction of [60]Fullerene and N-Sulfonylaldimines: Competing Formation of Hydrobenzylated [60]Fullerenes and 1,2-Dihydrofullerene
(2012-07-01)
Rajeshkumar, Venkatachalam
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
A system based on late transition-metal halides, phosphanes, water, and reducing agents in 1,2-dichlorobenzene can efficiently catalyze the intermolecular reductive coupling of [60]fullerene with N-sulfonylaldimines to afford novel 1,2-hydrobenzylated [60]fullerene derivatives. We found that both group VII?B metals (cobalt, rhodium, iridium) and group VIII?B metals (nickel, palladium, platinum) perform this coupling reaction. A control experiment in the absence of aldimines produced C60H2, which showed that the reaction might proceed via a [60]fullerene metal complex [M(?2-C60)(ligand)]. An isotope labeling experiment with D2O as deuterium source resulted in deuterioaryzilation with deuterium bonded to the sp3-carbon of C60, providing evidence of a five-membered azametallacycle intermediate. Evaluation of the scope of reductive coupling reaction with versatile aldimines gave access to the hydroaryzilation products. All the reductive coupling products were completely characterized by IR and NMR spectroscopy and ESI mass spectrometry. A possible reaction mechanism based on these results is proposed. This discovery of the formation of reductive coupling compounds and metal-catalyzed formation of C60H2 are both new to metal catalysis and fullerene chemistry.
Fullerene Derivatives Incorporating Phosphoramidous Ylide and Phosphoramidate: Synthesis and Property
(2009-07-03)
Chen, Sheng-Yuan
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Cheng, Rai-Long
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Tseng, Cheng-Kuo
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Lin, Ya-Shiuan
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Lai, Li-Hsiang
The reaction of dimethyl acetylenedicarboxylate (DMAD) with C(60) in the presence of hexamethylphosphorous triamide (HMPT) or hexaethylphosphorus triamide (HEPT) results in fullerene derivatives incorporating HMPT or HEPT ylides. The ylide derivatives exhibit unusual electronic absorptions in the visible region (435-660 nm), likely due to the presence of the ylide moiety. Electrochemical studies revealed that the first reductive potential of these compounds was more negative relative to those of both C(60) (Delta E = 130 mV) and a simple Bingel adduct (Delta E = 90 mV). A phosphoramidate side product, which resulted from the addition of HMPT or HEPT to C(60) followed by hydrolysis, exhibited a featureless absorption spectrum in the visible region and a more negative first reductive potential (Delta E = 70 mV) relative to that of C(60).
High-Performance and Highly Durable Inverted Organic Photovoltaics Embedding Solution-Processable Vanadium Oxides as an Interfacial Hole-Transporting Layer
(2011-09-01)
Chen, Chih-Ping
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Chen, Yeu-Ding
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
Inverted OPV devices based on sol-gel derived vanadium oxides (VO(x)) as an interfacial layer are demonstrated. The VO(x) shows excellent characteristics as a hole-transporting and protecting layer. The constructed devices exhibit enhanced performance with the studied polymers and are highly durable under accelerated conditions for long time periods.
Highly diastereoselective synthesis of substituted cyclopentenes through multicomponent reactions of phosphines, enynedioates, and benzylidene malononitriles via an unexpected phosphine alpha-addition-delta-evolvement of an anion pathway
(2016-03-13)
Chuang, Shih-Ching
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Sung, Shih-Ping
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應用化學系
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Department of Applied Chemistry
Highly Thermal Stable and Efficient Organic Photovoltaic Cells with Crosslinked Networks Appending Open-Cage Fullerenes as Additives
(2015-01-14)
Chen, Chih-Ping
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Huang, Chien-Yu
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
Highly thermal stable organic bulk heterojunction (OBHJ) photovoltaic cells are demonstrated with crosslinkable open-cage fullerenes (COF) as additives in the active layer. Partial incorporation of COF, approximate to 10-15 wt% with weight ratio of P3HT:PC61BM = 1:0.9, builds up three-dimensional local borders upon heating treatment at 150 degrees C for 10 min. This process induces crosslinking chemical reaction through activating the styryl moiety in COF and reduces phase aggregation rates of fullerenes materials. Supported by statistics of devices degradation data analysis and optical microscopy study, the devices with COF show longer lifetime with keeping their efficiency (t = 144 h) under accelerated heating test at 150 degrees C, while PCE of normal devices without COF drop dramatically. These results demonstrate that the thermally crosslinkable COF is an excellent additive for highly thermal stable and durable OPVs applications.
Impact of the Valence Charge of Transition Metals on the Cobalt- and Rhodium-Catalyzed Synthesis of Indenamines, Indenols, and Isoquinolinium Salts: A Catalytic Cycle Involving M-III/M-V [M = Co, Rh] for [4+2] Annulation
(2018-08-03)
Chiou, Mong-Feng
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Jayakumar, Jayachandran
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Cheng, Chien-Hong
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Chuang, Shih-Ching
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應用化學系
Reaction mechanisms for the synthesis of indenamines, indenols, and isoquinolinium salts through cobalt- and rhodium-catalysis were investigated using density functional theory calculations. We found that the valence charge of transition metals dramatically influences the reaction pathways. Catalytic reactions involving lower-oxidation-state transition metals (M-I/M-III, M = Co and Rh) generally favor a [3 + 2] cyclization pathway, whereas those involving higher oxidation states (M-III/M-V) proceed through a [4 + 2] cyclization pathway. A catalytic cycle with novel M-III/M-V as a crucial species was successfully revealed for isoquinolinium salts synthesis, in which highly valent M-V was encountered not only in the [RhCp*]-catalysis but also in the [CoCp*]-catalysis.
Iptycenes with an acridinone motif developed through [4+2] cycloaddition of tethered naphthalene and iminoquinone via a radical reaction
(2017-06-11)
Raju, Selvam
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Annamalai, Pratheepkumar
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Chen, Pei-Ling
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Liu, Yi-Hung
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Chuang, Shih-Ching
A new class of iptycenes was developed by combining 2-(naphthalen-1-yl) anilines and p-benzoquinones through copper( II)-mediated radical cyclisation. This unusual cyclisation reaction resulted in the robust and efficient syntheses of iptycenes with an acridinone motif. These iptycenes can be further transformed into planar acridinone heterocyclics through the Diels-Alder reaction.
Isatin derivatives and isoxazolinones from tandem anti-Michael three-component assembly and oxidation
(2014-08-10)
Deng, Jie-Cheng
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Chuang, Shih-Ching
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交大名義發表
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National Chiao Tung University
Low-temperature, simple and efficient preparation of perovskite solar cells using Lewis bases urea and thiourea as additives: stimulating large grain growth and providing a PCE up to 18.8%
(2018-01-01)
Hsieh, Cheng-Ming
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Liao, Yung-Sheng
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Lin, Yan-Ru
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Chen, Chih-Ping
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Tsai, Cheng-Min
We demonstrated that two Lewis bases - urea and thiourea - acted as efficient additives for CH3NH3(MA)PbI3-xClx and MAPbI(3) perovskite solar cells (PSCs) and observed a significant increase in PCE for the MAPbI(3) devices in the presence of 1% urea with a remarkable PCE of 18.8% using an extremely low annealing temperature (85 degrees C).
Mono- and bis-norbornene annulated biarylamines through pseudo-Catellani intermediates by Pd-catalyzed C-H activation
(2019-08-25)
Chuang, Shih-Ching
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交大名義發表
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National Chiao Tung University