Low-Band-Gap Conjugated Polymers. Improved Model Compounds for the Structural Analysis of Poly(isothianaphthene)

Kiebooms, R.; Hoogmartens, I.; Adriaensens, Peter; Vanderzande, Dirk; Gelan, Jan

doi:10.1021/ma00118a025

Cited by 30 publications

(30 citation statements)

References 4 publications

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“…Spectra were taken in a UV-vis-NIR quartz optical cell (100-QX, Hellma) with a JASCO V-570 UV-vis-NIR spectrophotometer. Monomers were polymerized on an indium tin oxide (ITO) working electrode (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)Delta Technologies,Stillwater). Films were electrodeposited as follows: monomers 4 and 6 were polymerized in TBAPC/ACN at 100 mV/s and 5 was polymerized in TBAPF 6 /DCM at 50 mV/s in cyclic voltammetry (CV) mode.…”

Section: Methodsmentioning

confidence: 99%

Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

Patra¹,

Wijsboom²,

Leitus³

et al. 2011

Chem. Mater.

180

107

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A series of new low-band-gap thieno-or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br 2 , 5Br 2 , and 6Br 2 ) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (∼0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

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Section: Methodsmentioning

confidence: 99%

Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

Patra¹,

Wijsboom²,

Leitus³

et al. 2011

Chem. Mater.

180

107

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“…The low bandgap can be attributed to the backbone of PTTEH being composed of thieno[3,4‐ b ]thiophene . As reported early, the unique structure of thieno[3,4‐ b ]thiophene is favorable to form quinoid structure as illustrated in Figure and thus extend the conjugation of the backbone, leading to low bandgap .…”

Section: Homo/lumo Energy Levelsmentioning

confidence: 71%

Highly Sensitive Field‐Effect Ammonia/Amine Sensors with Low Driving Voltage Based on Low Bandgap Polymers

Wang

Liu

Chen

et al. 2018

Adv Elect Materials

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and chemiluminescence. [6][7][8][9][10][11][12][13][14][15][16][17] However, these approaches have certain limitations, such as the requirement of expensive and sophisticated instrumentation, or extensive sample preparation prior to analysis. Therefore, there is a need for simple sensing methods that are portable, highly efficient, and selective, and enable in situ and realtime detection of ammonia and amines.Electrical sensors, which use electrical current as the output signal, generally possess simple device configurations and are capable of sensing in real time. Among them, organic and polymeric field-effect transistor (FET)-based sensors have shown potentials for portable, selective, sensitive, and low-cost gas sensors toward chemical, biological, and physical monitoring. [18][19][20][21][22][23] Recently, several groups have reported ammonia sensors based on organic and polymeric field-effect transistors. [24][25][26][27][28][29][30][31][32] For instance, Müllen and co-workers described highly sensitive and fast-responsive field-effect ammonia sensors based on ultrathin film of 4-6 molecular layers. [24] Diao and co-workers separately prepared porous thin film organic FET-based ammonia sensors, which facilitate the diffusion of analyte molecules into the dielectric/semiconductor interface to improve the sensitivity of organic FET sensors down to 1 ppb. [26,31] Some of us reported thin film of a conjugated polymer with nanopores, which were formed after thermal annealing, and the resulting FETs displayed selective and sensitive response to ammonia. [29] However, most of the FET-based sensors were operated under large driving voltages (drain-source and gate voltages: |V DS | and |V GS |) even up to 80 V. [24,25,29] Additionally, ultrathin and even monolayer or porous thin film devices were needed to improve their sensitivities (Table S1, Supporting Information). [24][25][26][27][28][29][30][31][32] Thus, FET-based sensors, which can be simply fabricated and operated at low driving voltages, while retaining the sensitivity, selectivity, and fast response, are desirable for practical applications.In this work, we report a highly sensitive and selective polymeric FET-based sensor for ammonia and amines, which can be operated with low voltages down to 5 V (for both |V DS | and |V GS |). As shown in Figure 1, we prepared a new semiconducting polymer poly [(4,6-thieno[3,4-b]thiophen-2-yl)-2-ethylhexan-1-one] (PTTEH). Due to the low bandgap (below 1 eV), the polymer thin film exhibits high working currents (I DS ) at low driving voltages (V DS = V GS = −5 V), which are ≈25 and ≈200 times higher than those of P3HT and PBDTTT-C-T, respectively. Ammonia/amine gas sensors have received increasing attention in recent years, due to their applications in monitoring of meat and seafood spoilage and air pollution as well as diagnosis of chronic diseases. Herein, a new conjugated polymer PTTEH is developed, which is composed of thieno[3,4-b] thiophene units, with very low bandgap. The low bandgap and the existence of radical s...

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“…Protection of α-positon of the thiophene ring of the isothianaphthene unit with silyl group has been carried out. Vanderzande group synthesized an isothianaphthene sandwiched monomer between thiophene units for improving stability, and carried out electrochemical polymerization [5] [8]. Resultant polymer shows low-bandgap nature derived from isothianaphthene, and shows good redox property.…”

Section: Introductionmentioning

confidence: 99%

Chiral-Electroactive Low-Bandgap Polymer Composite

Eguchi¹,

Kawabata²,

Goto³

2017

MSCE

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Electrochemical polymerization of an isothianaphthene based monomer for low-bandgap polymer was carried out in a polymer lyotropic liquid crystal. We prepared hydroxypropyl cellulose/N,N-dimethylformamide (HPC/DMF) lyotropic liquid crystal system as an electrolyte solution to perform electrochemical polymerization of a hydrophobic monomer, although water was commonly employed as a solvent for HPC. Resultant polymer prepared in HPC/DMF shows both electro-activity and optical activity. Fourier transform infrared absorption spectroscopy measurement reveals that the resultant material is composite of HPC and polyisothianaphthene based.

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Low-Band-Gap Conjugated Polymers. Improved Model Compounds for the Structural Analysis of Poly(isothianaphthene)

Cited by 30 publications

References 4 publications

Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

Highly Sensitive Field‐Effect Ammonia/Amine Sensors with Low Driving Voltage Based on Low Bandgap Polymers

Chiral-Electroactive Low-Bandgap Polymer Composite

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