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Synthesis and Characterization of Donor-Acceptor Poly(3-hexylthiophene) Copolymers Presenting 1,3,4-Oxadiazole Units and Their Application to Photovoltaic Cells
(2010-08-01)
Wang, Hsu-Shen
;
Su, Ming-Shin
;
Wei, Kung-Hwa
;
材料科學與工程學系
;
Department of Materials Science and Engineering
We have used Grignard metathesis polymerization to prepare poly(3-hexylthiophene)-based copolymers containing electron-withdrawing 4-tert-butylphenyl-1,3,4-oxadiazole-Phenyl moieties as side chains. We characterized these copolymers using (1)H and (13)C nuclear magnetic resonance spectroscopy, thermogravimetric analysis, and gel permeation chromatography. The band gap energy of copolymer was determined from the onset of the optical absorption. The quenching effects were observed in the photoluminescence spectra of the copolymers incorporating pendant electron-deficient 1,3,4-oxadiazole moieties on the side chains. The photocurrents of devices were enhanced in the presence of an optimal amount of the 1,3,4-oxadiazole moieties, thereby leading to improved power conversion efficiencies. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3331-3339, 2010
Synthesis and Characterization of a Thiadiazole/Benzoimidazole-Based Copolymer for Solar Cell Applications
(2010-09-15)
Chen, Guan-yu
;
Lan, Shang-che
;
Lin, Po-yu
;
Chu, Chih-wei
;
Wei, Kung-hwa
In this study, we synthesized a new polymer, PCTDBI, containing alternating carbazole and thiadiazole-benzoimidazole (TDBI) units. This polymer (number-average molecular weight - 25,600 g mol(-1)), which features a planar imidazole structure into the polymeric main chain, possesses reasonably good thermal properties (T(g) = 105 degrees C; T(d) = 396 degrees C) and an optical band gap of 1.75 eV that matches the maximum photon flux of sunlight. Electrochemical measurements revealed an appropriate energy band offset between the polymer's lowest unoccupied molecular orbital and that of PCBM, thereby allowing efficient electron transfer between the two species. A solar cell device incorporating PCTDBI and PCBM at a blend ratio of 1: 2 (w/w) exhibited a power conversion efficiency of 1.20%; the corresponding device incorporating PCTDBI and PC(71)BM (1: 2, w/w) exhibited a PCE of 1.84%. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 4456-4464, 2010
Synthesis and Applications of Low-Bandgap Conjugated Polymers Containing Phenothiazine Donor and Various Benzodiazole Acceptors for Polymer Solar Cells
(2010-11-01)
Padhy, Harihara
;
Huang, Jen-Hsien
;
Sahu, Duryodhan
;
Patra, Dhananjaya
;
Kekuda, Dhananjay
A series of soluble donor-acceptor conjugated polymers comprising of phenothiazine donor and various benzodiazole acceptors (i.e., benzothiadiazole, benzoselenodiazole, and benzoxadiazole) sandwiched between hexyl-thiophene linkers were designed, synthesized, and used for the fabrication of polymer solar cells (PSC). The effects of the benzodiazole acceptors on the thermal, optical, electrochemical, and photovoltaic properties of these low-bandgap (LBG) polymers were investigated. These LBG polymers possessed large molecular weight (M(n)) in the range of 3.85-5.13 x 10(4) with high thermal decomposition temperatures, which demonstrated broad absorption in the region of 300-750 nm with optical bandgaps of 1.80-1.93 eV. Both the HOMO energy level (-5.38 to -5.47 eV) and LUMO energy level (-3.47 to -3.60 eV) of the LBG polymers were within the desirable range of ideal energy level. Under 100 mW/cm(2) of AM 1.5 white-light illumination, bulk heterojunction PSC devices containing an active layer of electron donor polymers mixed with electron acceptor [6,6]-phenyl-C(61)-butyric acid methyl ester (PC(61)BM) or [6,6]-phenyl-C(71)-butyric acid methyl ester (PC(71)BM) in different weight ratios were investigated. The best performance of the PSC device was obtained by using polymer PP6DHTBT as an electron donor and PC(71)BM as an acceptor in the weight ratio of 1:4, and a power conversion efficiency value of 1.20%, an open-circuit voltage (V(oc)) value of 0.75 V, a short-circuit current (J(sc)) value of 4.60 mA/cm(2), and a fill factor (FF) value of 35.0% were achieved. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 4823-4834, 2010
Significant glass-transition-temperature increase through hydrogen-bonded copolymers
(2002-10-01)
Kuo, SW
;
Xu, HY
;
Huang, CF
;
Chang, FC
;
應用化學系
The role of hydrogen bonding in promoting intermolecular cohesion and higher glass-transition temperatures of polymer is a subject of longstanding interest. A series of poly(vinylphenol-co-vinylpyrrolidone) copolymers were prepared by the free-radical copolymerization of acetoxystyrene and vinylpyrrolidone; this was followed by the selective removal of the acetyl protective group, with corresponding and significant glass-transition-temperature increases after this procedure. The incorporation of acetoxystyrene into poly(vinylpyrrolidone) resulted in lower glass-transition temperatures because of the reduced dipole interactions in its homopolymers. However, the deacetylation of acetoxystyrene to transform the poly(vinylphenol-co-vinylpyrrolidone) copolymer enhanced the higher glass-transition temperature because of the strong hydrogen bonding in the copolymer chain. The thermal properties and hydrogen bonding of these two copolymers were investigated with differential scanning calorimetry and Fourier transform infrared spectroscopy, and good correlations between the thermal behaviors and IR results were observed. (C) 2002 Wiley Periodicals, Inc.
Blends of poly(propylene) and polyacetal compatibilized by ethylene vinyl alcohol copolymers
(2003-08-08)
Huang, JM
;
Cheng, HJ
;
Wu, JS
;
Chang, FC
;
應用化學系
Polymer blends of poly(propylene) (PP) and polyacetal (polyoxymethylene, POM) with ethylene vinyl alcohol (EVOH) copolymers were investigated by differential scanning calorimetry (DSC), rheological, tensile, and impact measurements, Fourier transform infrared spectroscopy (FTIR), and scanning electron microscopy (SEM). The PP-POM-EVOH blends were extruded with a co-rotating twin-screw extruder. The ethylene group in the EVOH is partially miscible with PP, whereas the hydroxyl group in the EVOH can form hydrogen bonding with POM. The EVOH tends to reside along the interface, acting as a surfactant to reduce the interfacial tension and to increase the interfacial adhesion between the blends. Results from SEM and mechanical tests indicate that a small quantity of the EVOH copolymer or a smaller vinyl alcohol content in the EVOH copolymer results in a better compatibilized blend in terms of finer phase domains and better mechanical properties. (C) 2003 Wiley Periodicals, Inc.
Synthesis and Applications of Cyano-Vinylene-Based Polymers Containing Cyclopentadithiophene and Dithienosilole Units for Photovoltaic Cells
(2011-08-01)
Padhy, Harihara
;
Sahu, Duryodhan
;
Patra, Dhananjaya
;
Pola, Murali Krishna
;
Huang, Jen-Hsien
Two beta-cyano-thiophenevinylene-based polymers containing cyclopentadithiophene (CPDT-CN) and dithienosilole (DTS-CN) units were synthesized via Stille coupling reaction with Pd(PPh(3))(4) as a catalyst. The effects of the bridged atoms (C and Si) and cyano-vinylene groups on their thermal, optical, electrochemical, charge transporting, and photovoltaic properties were investigated. Both polymers possessed the highest occupied molecular orbital (HOMO) levels of about -5.30 eV and the lowest unoccupied molecular orbital (LUMO) levels of about -3.60 eV, and covered broad absorption ranges with narrow optical band gaps (ca. 1.6 eV). The bulk heterojunction polymer solar cell (PSC) devices containing an active layer of electron-donor polymers (CPDT-CN and DTS-CN) blended with an electron-acceptor, that is, [6,6]-phenyl-C(61)-butyric acid methyl ester (PC(61)BM) or [6,6]-phenyl-C(71)-butyric acid methyl ester (PC(71)BM), in different weight ratios were explored under 100 mW/cm(2) of AM 1.5 white-light illumination. The PSC device based on DTS-CN:PC(71)BM (1:2 w/w) exhibited a best power conversion efficiency (PCE) value of 2.25% with V(oc) = 0.74 V, J(sc) = 8.39 mA/cm(2), and FF = 0.36. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3417-3425, 2011
Synthesis and Electroluminescence Properties of White-Light Single Polyfluorenes with High-Molecular Weight by Click Reaction
(2011-08-01)
Lo, Chih-Nan
;
Hsu, Chain-Shu
;
應用化學系
;
Department of Applied Chemistry
We reported a new way to synthesize single-chain white light-emitting polyfluorene (WPF) with an increased molecular weight using azide-alkyne click reaction. Four basic polymers with specific end-capping, which exhibited high-glass transition temperatures (T(g) > 100 degrees C) and excellent thermal stability, were used as foundations of the WPF's synthesis; a blue-light polymer (PFB2) end-capped with azide groups can easily react with acetylene end-capped polymers (PFB1, PFG1, and PFR1, which are emitting blue-, green- and red-light, respectively) to form triazole-ring linkages in polar solvents such as N,N-dimethylforamide/toluene co-solvent at moderate temperature of 100 degrees C, even without metal-catalyst. Several WPFs that consist of these four basic polymers in certain ratios were derived, and the polymer light-emitting diode device based on the high-molecular weight WPF was achieved and demonstrated a maximum brightness of 7551 cd/m(2) (at 12.5 V) and a maximum yield of 5.5 cd/A with Commission Internationale de l'Eclairage coordinates of (0.30, 0.33) using fine-tuned WPF5 as emitting material. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 3355-3365, 2011
A Pentacyclic Nitrogen-Bridged Thienyl-Phenylene-Thienyl Arene for Donor-Acceptor Copolymers: Synthesis, Characterization, and Applications in Field-Effect Transistors and Polymer Solar Cells
(2012-09-01)
Tseng, Cheng-An
;
Wu, Jhong-Sian
;
Lin, Tai-Yen
;
Kao, Wei-Shun
;
Wu, Cheng-En
A pentacyclic benzodipyrrolothiophene (BDPT) unit, in which two outer thiophene rings are covalently fastened with the central phenylene ring by nitrogen bridges, was synthesized. The two pyrrole units embedded in BDPT were constructed by using one-pot palladium-catalyzed amination. The coplanar stannylated Sn-BDPT building block was copolymerized with electron-deficient thieno[3,4-c]pyrrole-4,6-dione (TPD), benzothiadiazole (BT), and dithienyl-diketopyrrolopyrrole (DPP) acceptors by Stille polymerization. The bridging nitrogen atoms make the BDPT motif highly electron-abundant and structurally coplanar, which allows for tailoring the optical and electronic properties of the resultant polymers. Strong photoinduced charge-transfer with significant band-broadening in the solid state and relatively higher oxidation potential are characteristic of the BDPT-based polymers. Poly(benzodipyrrolothiophene-alt-benzothiadiazole) (PBDPTBT) achieved the highest field-effect hole mobility of up to 0.02 cm2?V-1?s-1. The photovoltaic device using the PBDPTBT/PC71BM blend (1:3, w/w) exhibited a Voc of 0.6 V, a Jsc of 10.34 mA?cm-2, and a FF of 50?%, leading to a decent PCE of 3.08?%. Encouragingly, the device incorporating poly(benzodipyrrolothiophene-alt-thienopyrrolodione) (PBDPTTPD)/PC71BM (1:3, w/w) composite delivered a highest PCE of 3.72?%. The enhanced performance arises from the lower-lying HOMO value of PBDPTTPD to yield a higher Voc of 0.72 V.
Effects of thiophene units on substituted benzothiadiazole and benzodithiophene copolymers for photovoltaic applications
(2012-09-05)
Ding, Ping
;
Zou, Yingping
;
Chu, Cheng-Che
;
Xiao, Dequan
;
Hsu, Chain-Shu
Two conjugated copolymers, poly{4,7-[5,6-bis(octyloxy)]benzo(c)(1,2,5)thiadiazole-alt-4,8-di(2-ethylhexyloxyl)benzo[1,2-b:3,4-b]dithiophene} (P1) and poly(2-{5-[5,6-bis(octyloxy)-4-(thiophen-2-yl)benzo(c)(1,2,5)thiadiazol-7-yl] thiophen-2-yl}-4,8-di(2-ethylhexyloxyl)benzo(1,2-b:3,4-b)dithiophene) (P2), composed of benzodithiophene and 5,6-dioctyloxybenzothiadiazole derivatives with or without thiophene units were synthesized via a Stille cross-coupling polymerization reaction. These copolymers are promising for applications in bulk heterojunction solar cells because of their good solubility, proper thermal stability, moderate hole mobility, and low band gap. The photovoltaic properties of these copolymers were investigated on the basis of blends of the different polymer/(6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) weight ratios under AM1.5G illumination at 100 mW/cm2. The device with indium tin oxide/poly(3,4-ethylene dioxythiophene):poly(styrene sulfonate)/P2:PC71BM (1 : 2 w/w)/Ca/Al gave a relatively better photovoltaic performance with a power conversion efficiency of 1.55%. (C) 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012
Dithienocyclopentathieno[3,2-b]thiophene Hexacyclic Arene for Solution-Processed Organic Field-Effect Transistors and Photovoltaic Applications
(2012-04-01)
Cheng, Yen-Ju
;
Chen, Chiu-Hsiang
;
Lin, Tai-Yen
;
Hsu, Chain-Shu
;
應用化學系
We have developed a ladder-type dithienocyclopentathieno[3,2-b]thiophene (DTCTT) hexacyclic unit in which the central thieno[3,2-b]thiophene ring was covalently fastened to two adjacent thiophene rings through carbon bridges, thereby forming two connected cyclopentadithiophene (CPDT) units in a hexacyclic coplanar structure. This stannylated Sn-DTCTT building block was copolymerized with three electron-deficient acceptors, dibromo-thieno[3,4-c]pyrrole-4,6-dione (TPD), dibromo-benzothiadiazole (BT), and dibromo-phenanthrenequinoxaline (PQX), by Stille polymerization, thereby furnishing a new class of alternating donoracceptor copolymers: PDTCTTTPD, PDTCTTBT, and PDTCTTPQX, respectively. Field-effect transistors based on PDTCTTPQX and PDTCTTBT yielded high hole mobilities of 0.017 and 0.053 cm2?V-1?s-1, respectively, which are among the highest performances among amorphous donoracceptor copolymers. A bulk heterojunction solar cell that incorporated PDTCTTTPD with the lower-lying HOMO energy level delivered a higher Voc value of 0.72 V and a power conversion efficiency (PCE) value of 2.59?%.

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