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Alkyl-Spacer Enhancement in Performance of Light-Emitting Electrochemical Cells
(1970-01-01)
Shiu, Ler-Chun
;
Chang, Bo-Ren
;
Hsiao, Miles C-S
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Sie, Wu-Sian
;
Wu, Ming-Lun
Synthetic, structural, photophysical, and electrochemical study of [Ir(ppy)(2)(py)(2)](BF4) (1(BF4)) and four di-N-N-bridged complexes of [Ir(ppy)(2)(bpa)](2)(BF4)(2)(2A(BF4)(2)), [Ir(ppy)(2)((cis-bpe))](2)(BF4)(2)(2B(BF4)(2)), [Ir(ppy)(2)(tmp)](2)(BF4)(2)(2C(BF4)(2)), and [Ir(ppy)(2)(bpy)](4)(BF4)(4)(3(BF4)(4)) are described with Hppy = 2-phenylpyridine, py = pyridine, N-N= dipyridyl ligands of 1,2-bis(4-pyridyl)ethane (bpa),cis-1,2-bis(4-pyridyl)ethylene (cis-bpe), 1,3-di(4-pyridyl)propane (tmp), and 4,4'-dipyridine (bpy). Five single-crystal structures of1(PF6),2A(NO3)(2),2A(PF6)(2),2B(PF6)(2), and3(NO3)(4)were determined, supporting the dibridged structures and presence of a variety of stereoisomers. Application of four luminescent complexes,1(BF4),2A(BF4)(2),2C(BF4)(2), and3(BF4)(4), in solid-state light-emitting electrochemical cells (LECs) is reported. The work demonstrates an effective approach to realize efficient LECs based on dibridged di- and multinuclear cationic transition-metal complexes with a suitably long alkyl spacer in the bridging ligand.
Solution-Processable Quinoidal Dithioalkylterthiophene-Based Small Molecules Pseudo-Pentathienoacenes via an Intramolecular S center dot center dot center dot S Lock for High-Performance n-Type Organic Field-Effect Transistors
(2020-06-03)
Vegiraju, Sureshraju
;
Torimtubun, Alfonsina Abat Amelenan
;
Lin, Po-Shen
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Tsai, Hsin-Chia
;
Lien, Wei-Chieh
A new organic small-molecule family comprising tetracyanoquinodimethane-substituted quinoidal dithioalky(SR)terthiophenes (DSTQs) (DSTQ-6 (1); SR = SC6H13, DSTQ : 10 (2); SR = SC10H21, DSTQ14 (3); SR = SC10H21) was synthesized and contrasted with a nonthioalkylated analogue (DRTQ14 (4); R = C14H29). The physical, electrochemical, and electrical properties of these new compounds are thoroughly investigated. Optimized geometries obtained from density functional theory calculations and single-crystal X-ray diffraction reveal the planarity of the SR-containing DSTQ core. DSTQs pack in a slipped pi-pi stacked two-dimensional arrangement, with a short intermolecular stacking distance of 3.55 A and short intermolecular S center dot center dot center dot N contacts of 3.56 angstrom. Thin-film morphological analysis by grazing incident X-ray diffraction reveals that all DSTQ molecules are packed in an edge-on fashion on the substrate. The favorable molecular packing, the high core planarity, and very low lowest unoccupied molecular orbital (LUMO) energy level (-4.2 eV) suggest that DSTQs could be electron-transporting semiconductors. Organic field-effect transistors based on solution-sheared DSTQ : 14 exhibit the highest electron mobility of 0.77 cm(2) V-1 s(-1) with good ambient stability, which is the highest value reported to date for such a solution process terthiophene-based small molecular semiconductor. These results demonstrate that the device performance of solution-sheared DSTQs can be improved by side chain engineering.
Pt-II Complexes with 6-(5-Trifluoromethyl-Pyrazol-3-yl)-2,2 '-Bipyridine Terdentate Chelating Ligands: Synthesis, Characterization, and Luminescent Properties
(2008-01-01)
Chen, Jing-Lin
;
Chang, Sheng-Yuan
;
Chi, Yun
;
Chen, Kellen
;
Cheng, Yi-Ming
A series of Pt-II complexes Pt(fpbpy)Cl (1), Pt(fpbpy)(OAc) (2), Pt(fpbpy)(NHCOMe) (3), Pt(fpbpy)(NHCOEt) (4), and [Pt(fpbpy)(NCMe)](BF4) (5) with deprotonated 6-(5-trifluoromethyl-pyrazol-3-yl)-2,2'-bipyridine terdentate ligand are prepared, among which 1 is converted to complexes 2-5 by a simple ligand substitution. Alternatively, acetamide complex 3 is prepared by hydrolysis of acetonitrile complex 5, while the back conversion from 3 to 1 is regulated by the addition of HCl solution, showing the reaction sequence 1 -> 5 -> 3 -> 1. Mullilayer OLED devices are successfully fabricated by using triphenyl-(4-(9-phenyl-9H-fluoren-9-yl)phenyl) silane (TPSi-F) as host material and with doping concentrations of 1 varying from 7 to 100%. The electroluminescence showed a substantial red-shifting versus the normal photoluminescence detected in solution. Moreover, at a doping concentration of 28%, the device showed a saturated red luminescence with a maximum external quantum yield of 8.5% at 20 mA cm(-2) and a peak luminescence of 47543 cd m(-2) at 18.5 V.
Theory-Guided Experiments on the Mechanistic Elucidation of the Reduction of Dinuclear Zinc, Manganese, and Cadmium Complexes
(2011)
Lu, Duan-Yen
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Yu, Jen-Shiang K.
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Kuo, Ting-Shen
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Lee, Gene-Hsiang
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Wang, Yu
Design and synthesis of triazolyl coumarins as Hg2+ selective fluorescent chemosensors
(2012)
Ho, I-Ting
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Lai, Ting-Ling
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Wu, Ren-Tsung
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Tsai, Ming-Tsung
;
Wu, Chun-Ming
A series of triazolyl coumarin derivatives L1-L4, with and without spacer groups between the coumarin and the triazole groups, were synthesized as fluorescent sensors to study their binding ability and selectivity toward metal ions. Ligand L3, which contains an acetyl linker between the triazole and the coumarin, exhibited a high selectivity toward Hg2+ in polar protic solvents MeOH-CHCl3 (9 : 1, v/v) with fluorescent enhancement, furthermore, it was found to bind two Hg2+ at a high concentration (>12.5 mM) of Hg(ClO4)(2). In contrast, L4, in which position 4 of the triazole unit was replaced by a benzyl group instead of the 4-tert-butylphenoxymethyl group used in L1-L3, showed a binding stoichiometry toward only one Hg2+. On the basis of the fluorescent sensing, IR, and H-1 NMR titration results of ligands L1-L4, we proposed that not only the acetyl C=O but also the ether group of the 4-tert-butylphenoxymethyl of L3 assisted the triazole nitrogen atoms in the complexation of Hg2+ to form a 1 : 2 complex (L3 center dot(Hg2+)(2)).
Stepwise Construction of the Cr-Cr Quintuple Bond and Its Destruction upon Axial Coordination
(2012)
Huang, Yu-Lun
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Lu, Duan-Yen
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Yu, Hsien-Cheng
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Yu, Jen-Shiang K.
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Hsu, Chia-Wei
Regioselectivity in the 1,3-dipolar cycloaddition of adamantylidenefulvene and its modification by inclusion in cyclodextrins' solutions
(2006-07-31)
Chu, Jean-Ho
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Li, Wan-Sheung
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Chao, Ito
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Lee, Gene-Hsiang
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Chung, Wen-Sheng
The 1,3-dipolar cycloaddition of adamantylidenefulvene (1) with 2 equiv of nitrile oxides 2a-d gave 1/1 cycloadducts, 3a-d and 4a-d, as the major products, and four other 1/2 minor cycloadducts 5-8a,b. The ratios of 1/1 cycloadducts 3a-d to 4a-d in THF solution were about 1/1 in the four different nitrile oxides 2a-d studied and microwave was found to accelerate the reactions and enhance their yields. It is noteworthy that the regioselectivity of 3a/4a was enhanced to 71/29 in beta-cyclodextrin (beta-CD) aqueous solution compared to that of 40/60 in the absence of P-CD. The regioselectivity of 3b/4b was further enhanced to 99/1 when 4-tert-butylphenyl hydroximinoyl chloride (9b) was complexed with beta-CD and then proceeded to react with 1; this is in sharp contrast with that of 33/67 in the absence of beta-CD. The binding constant of 1 center dot beta-CD in acetone-d(6)/D2O (1/1) was determined to be 188 +/- 9 M-1 by H-1 NMR titration experiments. The binding mode of 1 center dot beta-CD was further determined by ROESY experiment. Furthermore, molecular dynamic simulations were carried out to provide information of the complexation modes of 1 center dot beta-CD, 3a center dot beta-CD, 4a center dot beta-CD, 9a center dot beta-CD, and 9b center dot beta-CD. It was found that both steric and electrostatic effects play important roles in determining the regio- and stereochemistry of 1,3-dipolar cycloaddition of 1. Finally, beta-CD is shown to serve as a chiral shift reagent to differentiate the enantiomers of 4a in H-1 NMR. (c) 2006 Elsevier Ltd. All rights reserved.
Orange and red organic light-emitting devices employing neutral Ru(II) emitters: Rational design and prospects for color tuning
(2006-08-04)
Tung, Yung-Liang
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Chen, Li-Shiuan
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Chi, Yun
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Chou, Pi-Tai
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Cheng, Yi-Ming
A new series of charge-neutral Ru(II) pyridyl and isoquinoline pyrazolate complexes, [Ru(bppz)(2)(PPh2Me)(2)] (bbpz: 3-tert-butyl-5-pyridyl pyrazolate) (1), [Ru(fppz)(2)(PPh2Me)(2)] (fppz: 3-trifluoromethyl-5-pyridyl pyrazolate) (2), [Ru(ibpz)(2)(PPhMe2)(2)] (ibpz: 3-tert-butyl-5-(1-isoquinolyl) pyrazolate) (3), [Ru(ibpz)(2)(PPh2Me)(2)] (4), [Ru(ifpz)(2)(PPh2Me)(2)] (ifpz: 3-trifluoromethyl-5-(1-isoquinolyl) pyrazolate) (5), [Ru(ibpz)(2)(dpp=)] (dpp= represents cis-1,2-bis-(diphenylphosphino)ethene) (6), and [Ru(ifpz)(2)(dpp=)] (7), have been synthesized, and their structural, electrochemical, and photophysical properties have been characterized. A comprehensive time-dependant density functional theory (TDDFT) approach has been used to assign the observed electronic transitions to specific frontier orbital configurations. A multilayer organic light-emitting device (OLED) using 24 wt % of 5 as the dopant emitter in a 4,4'-N,N'-dicarbazolyl-1,1'-biphenyl (CBP) host with 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) as the hole-transport layer exhibits saturated red emission with an external quantum efficiency (EQE) of 5.10%, luminous efficiency of 5.74 cd A(-1), and power efficiency of 2.62 lm W-1. The incorporation of a thin layer of poly(styrene sulfonate)-doped poly(3,4-ethylenedioxythiophene) (PEDOT) between indium tin oxide (ITO) and NPB gave anoptimized device with an EQE of 7.03%, luminous efficiency of 8.02 cd A(-1), and power efficiency of 2.74 lm W-1 at 20 mA cm(-2). These values represent a breakthrough in the field of OLEDs using less expensive Ru(II) metal complexes. The nonionic nature of the complexes as well as their high emission quantum efficiencies and short radiative lifetimes are believed to be the key factors enabling this unprecedented achievement. The prospects for color tuning based on Ru(II) complexes are also discussed in light of some theoretical calculations.
A novel photoinduced ring opening and isomerization of adamantane-2-spiro isoxazolines using MO(CO)(6)
(2006-10-02)
Senthilvelan, Annamalai
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Lee, Gene-Hsiang
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Chung, Wen-Sheng
;
應用化學系
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Department of Applied Chemistry
The MO(Co)(6)-mediated photoinduced ring-opening reactions of adamantane isoxazolines involve novel rearrangement that provide enaminoketones as major products and beta-hydroxy ketones as minor ones; in contrast, only beta-hydroxy ketones and alpha,beta-unsaturated ketones were obtained under thermal condition. (c) 2006 Elsevier Ltd. All rights reserved.
Capping the upper and lower rims of calix[4]arenes by aryl dinitrile oxide reactions
(2006-11-20)
Shiao, Ya-Jiun
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Chiang, Pei-Chen
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Senthilvelan, Annamalai
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Tsai, Ming-Tsung
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Lee, Gene-Hsiang
1, 3-Dipolar cycloadditions of upper- and lower-rim diallylcalix[4]arenes (1 and 3) with aryl dinitrile oxides provide a unique and efficient way of capping the calix[4]arenes. When dinitrile oxides reacted with 5-allylcalix[4]arene 7, they underwent a 1,3-dipolar cycloaddition on one side and an electrophilic substitution on the other side, which led to a novel type of asymmetric calix[4]arenes (9 and 12). (c) 2006 Elsevier Ltd. All rights reserved.

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