Novel Thiophene‐Thiazolothiazole Copolymers for Organic Field‐Effect Transistors

Osaka, Itaru; Sauvé, Geneviève; Zhang, Rui; Kowalewski, Tomasz; McCullough, Richard D.

doi:10.1002/adma.200701058

Cited by 288 publications

(241 citation statements)

References 40 publications

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“…The length of the oligothiophene unit varied from 6 to 8 thiophene rings and thieno [3,2-b]thiophene-bridged 4 thiophene rings. To our knowledge, there are a few examples in the literature on the low-bandgap copolymers consisting of oligothiophenes and electron acceptors (quinoxaline, 14 oxadiazole, 15 benzothiadiazole, 16 or thiazolothiazole 17 ). However, the maximum number of thiophene rings in the oligothiophene segments is no more than 4.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Alternating Regioregular Oligothiophenes/Benzothiadiazole Copolymers for Organic Solar Cells

et al. 2009

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Received May 4, 2009; Revised Manuscript Received July 6, 2009 ABSTRACT: Low-bandgap regioregular polythiophene derivatives, PTh 6 BTD, PTh 8 BTD, and PTh 4 TTBTD, were synthesized through Stille coupling reaction. These are alternating copolymers of an electron-deficient benzothiadiazole unit and oligothiophene units including hexathiophene, octathiophene, and thieno[3,2-b]thiophene-bridged quarterthiophene, respectively. The polymers are soluble in halogenated solvents such as o-dichlorobenzene, affording good processability in solar cell fabrication. Meanwhile, the synthesized alternating copolymers show much broader absorption than P3HT, covering the spectral region from 350 to 800 nm. DSC analysis showed that all three polymers readily crystallized, indicating highly ordered intermolecular packing, which is beneficial for achieving higher charge carrier mobility. Bulkheterojunction solar cells using 1:1 w/w PTh n BTD:PC 61 BM ([6,6]-phenyl C 61 -butyric acid methyl ester) blends as the photovoltaic active layers were fabricated and characterized. Best power conversion efficiency of 1.7% was obtained from PTh 8 BTD-based devices under a simulated AM 1.5 G solar irradiation of 100 mW/cm 2 .

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Alternating Regioregular Oligothiophenes/Benzothiadiazole Copolymers for Organic Solar Cells

et al. 2009

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“…Scheme I. Synthesis of 2,6-dibromo-1,5-naphthyridine (6) The characteristic FTIR, proton and carbon spectra of 2,6-Dibromo-1,5-naphthyridine (6) are given below in Figures 1-3. 3.…”

Section: Resultsmentioning

confidence: 99%

“…3. Carbon NMR spectra of 2,6-Dibromo-1,5-naphthyridine (6) Having secured the synthesis of monomer 6 we next moved towards the synthesis of the monomer 8. To this end, lithium bromine exchange of compound 7 at lower temperature followed quenching the anion with isopropoxy borolane gave monomer 8 in good yield (Scheme II).…”

Section: Resultsmentioning

confidence: 99%

“…Several classes of polyconjugated molecules of high molecular weight (polymers), and of relatively low molecular weight (oligomers), have been synthesized. Polythiophenes, polypyroles and other polymers with heteroatoms in the polymer main chain are considered among the most important classes of heterocyclic polymers with extended n-conjugation [6][7][8][9][10]. The preparation of such polymeric materials often involves metal-catalyzed cross-coupling reactions, and frequently requires long reaction time to yield high-molecularweight material.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Functionalized Polythiophene as a Potenial Organic Semi-Conductor

Siddiqui

Ullah

Al‐Betar

et al. 2016

MATEC Web of Conferences

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Abstract. The synthesis Poly [1,5-naphthyridine-(3-hexylthiophene)] (PN3HTh) semi-conducting polymer has been accomplished by adopting both conventional and microwave-assisted Suzuki-Miyaura cross-coupling reaction between 3-hexylthiophene-2,5-diboronic ester and 2,6-dibromo-1,5-naphthyridine. The electrochemical and transport properties of PN3HTh were investigated both in the bulk as well as in thin film form. These properties can be further tuned by changing the solvent and the nature of the electrode used. Consequently, cyclic voltammetry (CV) measurements were conducted using a potentiostat coupled with an electrochemical cell. The CV results of PN3HTh as a bulk form in H2SO4 solution indicated that the concentration of the polymer in the solution is not well defined because of polymer poor solubility in aqueous solutions. On the other hand, the sulfur group which works as electron donating makes the system more electron-rich. This can explain by the absence of the reduction peak. For the thin film, two single oxidation peaks were obtained at around 0 V and 0.3 V for both cases. Different solvents can tune the transport properties of the polymer as can be seen from the two CVs where BF3 exhibited enhanced transport properties over ACN. The synthesized polymers were characterized by modern spectroscopic methods including IR and NMR.

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“…15,[20][21][22][23][24][25][26][27][28][29][30] We have reported on a series of TzTz-based polymers with alkylthiophenes as the donor unit. 15,[20][21][22][23]31,32 One of the highest performing polymers was PTzBT-BOHD (Fig. 1a), which demonstrated quite high PCEs of ³7.5% in conventional single-junction cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of an Alkoxythiazole-thiazolothiazole Semiconducting Polymer for Organic Solar Cells

Saito

Osaka

2017

Electrochemistry

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We report the synthesis and characterization of a new thiazolothiazole (TzTz)-based semiconducting polymer incorporating the alkoxythiazole unit in the polymer backbone (PTzTTz-BOoHD). The introduction of the alkoxythiazole unit in a thiophene-TzTz polymer (PTzBT-BOHD) lowered the LUMO energy level while keeping the HOMO energy level, resulting in a narrower bandgap. The solar cell with PTzTTz-BOoHD showed photoresponse in a wider spectral range (~740 nm) compared to that with PTzBT-BOHD and with a thiophene-TzTz polymer having the alkoxy thiophene unit (PTzBT-BOoHD). Although the fill factor (FF) of the cell based on PTzTTz-BOoHD was lower than the cell based on PTzBT-BOHD and -BOoHD, the maximum PCE of the cell based on PTzTTz-BOoHD resulted in 6.2%, which was comparable to and higher than the cell based on PTzBT-BOHD and -BOoHD, respectively. While PTzTTz-BOoHD showed good crystallinity in the polymer film, it was reduced in the film blended with PC 61 BM, which is likely an origin of the drop of FF. As PTzTTz-BOoHD has more suitable electronic structures for solar cells such as a deep HOMO level and a narrow bandgap, compared to the other two polymers, we expect that PTzTTz-BOoHD would demonstrate higher PCE by further device optimization.

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Novel Thiophene‐Thiazolothiazole Copolymers for Organic Field‐Effect Transistors

Cited by 288 publications

References 40 publications

Design and Synthesis of Alternating Regioregular Oligothiophenes/Benzothiadiazole Copolymers for Organic Solar Cells

Design and Synthesis of Alternating Regioregular Oligothiophenes/Benzothiadiazole Copolymers for Organic Solar Cells

Synthesis of Functionalized Polythiophene as a Potenial Organic Semi-Conductor

Synthesis and Characterization of an Alkoxythiazole-thiazolothiazole Semiconducting Polymer for Organic Solar Cells

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