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A benzoselenadiazole-based low band gap polymer synthesis and photovoltaic application

  • 17.07.2019
RSC Advances7 30Chemistry Lettersall purchased from Puyang Huicheng Electronic Material Co. Materials 4,7-dibromo-2,1,3-benzoselenadiazole BSe3-hexylthiophene, 3,4-dihexyloxythiophene, and 3,4-dioctyloxythiophene were IrO2, soluble polymeric electrochromic materials have some merits, including. Known for its Beehive like structure, the entrance to and a threat to their way of life.

Poly thiophenes represent an important class of electrochromic materials due to their intense color changes, robust environmental and redox stabilities, and facile structural modifications.

Soluble poly thiophenes have been prepared by substituting the 3- or 4-, or both 3- and 4- positions of the thiophene ring with flexible units, such as alkyl, alkoxy, or alkylenedioxy units [ 12 ].

Thiophenes and their derivatives are also frequently used as the donor units for the preparation of D-A-type polymers with the acceptor units electron-deficient units [ 12 ]. In addition, as redox-active chromophores, the alkyl-substituted carbazole and fluorene has been used as the donor units for the construction of D-A-type polymeric electrochromic materials, which usually present multichromic properties, depending on the selection of the constitutional units [ 14 , 15 , 16 ].

Meanwhile, the formation of interchain Se—Se interactions could also be anticipated and be attributed to the better polarizability of the Se atom compared to the sulfur atom, which leads to the higher charge carrier mobility of the Se-containing polymers [ 17 , 18 , 19 ].

Selenophene and benzoselenadiazole BSe are two common heteroaromatic compounds and carriers of Se atoms, which are used as electron-donating and electron-deficient building blocks, respectively, for the preparation of D-A-type conjugated polymers [ 17 , 18 , 19 ].

Besides the BSe unit, its derivatives including 4,7-dibromo-5,6-bis octyloxy -[2,1,3]-benzoselenadiazole BSeoc or 4,7-bis 5-bromothiopheneyl -5,6-bis octyloxy -[2,1,3]-benzoselenadiazole DTBSe have also been employed as electron-accepting units [ 17 ], and the introduction of the alkoxy units was considered to be able to increase the solubility of the resultant polymers.

Hyun reported that the replacement of thiophene with selenophene in the BSeoc-containing polymers led to the lower bandgap and higher photovoltaic performance compared to its thiophene-containing analogues [ 8 ]. BSe- or selenophene-containing conjugated polymers were also prepared and characterized in terms of their electrochromic properties, which usually showed lower bandgaps and higher redox stabilities than that of their analogues [ 4 , 24 ].

A soluble copolymer consisting of BSe and 2,5-bis-dithienyl-1H-pyrrole has been synthesized by Koyuncu et al. To date, the reports on soluble BSe-containing electrochromic polymers are few, which should be further extended and strengthened due to the good application records of BSe and its derivatives in the field of organic photovoltaics OPVs [ 25 ].

In this report, we prepared six conjugated polymers with 4,7-bis 5-bromohexythiophenyl benzo[c][1,2,5]selenadiazole 2Br-HT-BSe , 4,7-bis 5-bromo-3,4-bis hexyloxy thiopheneyl benzo[c][1,2,5]selenadiazole 2Br-HoT-BSe , and 4,7-bis 5-bromo-3,4-bis octyloxy thiopheneyl benzo[c][1,2,5]selenadiazole 2Br-OoT-BSe as the electron accepting units, and 9- octylnonylyl -2,7-bis 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl -9H-carbazole BAcarb or 2,7-bis 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl -9,9-dioctylfluorene BAfluo as the electron-donating units.

The structures of the above three acceptor units and six alternating copolymers are shown in Scheme 1 and Scheme 2. The effects of the side-chain substituent located on the thiophene ring and the electron-donating units on the electrochromic properties of the resultant polymers are summarized and discussed in detail. Experimental Section 2. Materials 4,7-dibromo-2,1,3-benzoselenadiazole BSe , 3-hexylthiophene, 3,4-dihexyloxythiophene, and 3,4-dioctyloxythiophene were all purchased from Puyang Huicheng Electronic Material Co.

The 2-substituted tributylstannane derivatives of the thiophene derivatives were prepared with the methods reported previously [ 25 ]. Shenzhen, China and used without further purification. SCE as the pseudo-reference electrode. The supporting electrolyte used for all electrochemical measurements was 0.

The three-electrode system was constructed on a quartz cell, with the polymer-coated ITO electrode as the working electrode WE electrode, and the Pt and Ag wires were used as the counter and reference electrodes, respectively. The chromatic coordinates of the polymers under different potentials were measured with the same apparatus as used in the spectroelectrochemical measurement with the employment of the chromaticity software Varian Inc.

Prior to each set of measurements, background color coordinates x, y, and z values were taken at open-circuit, using the electrolyte solution without the polymer films under study. Digital photographs of the polymer films were taken by a Canon Canon Inc. Manna, and Apurba K. Chemistry of Materials , 27 19 , Kobilka, and Benjamin J. Macromolecules , 47 21 , Lin, and Kung-Hwa Wei.

Macromolecules , 47 20 , Dana D. ACS Nano , 8 4 , Rycel L. Macromolecules , 47 7 , Macromolecules , 47 5 , Journal of the American Chemical Society , 45 , Macromolecules , 46 19 , Selenium and Tellurium Containing Conjugated Polymers.

Chapman, Neil J. Findlay, Peter J. Skabara, Peter N. Horton, Simon J. Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics. Journal of Materials Chemistry C , 6 14 , Cyano-substituted benzochalcogenadiazole-based polymer semiconductors for balanced ambipolar organic thin-film transistors. Polymer Chemistry , 9 28 , Chemistry Letters , 46 8 , Itaru Osaka, Kazuo Takimiya.

Advanced Materials , 29 25 , Polymers , 9 7 , Chemical Physics Letters , , Metal carbonyl complexes of potentially ambidentate 2,1,3-benzothiadiazole and 2,1,3-benzoselenadiazole acceptors. Can time-dependent density functional theory predict intersystem crossing in organic chromophores? A case study on benzo bis -X-diazole based donor—acceptor—donor type molecules.

Physical Chemistry Chemical Physics , 19 24 , Effects of the acceptor pattern and substitution position on the properties of N-phenyl-carbazolyl based donor—acceptor—donor molecules. RSC Advances , 7 30 , Hacioglu, Levent Toppare. Syntheses, electrochemical and spectroelectrochemical characterization of benzothiadiazole and benzoselenadiazole based random copolymers.

Journal of Macromolecular Science, Part A , 53 8 ,

Polymers9 7Keywords: benzoselenadiazole, carbazole, fluorene, polymers for polymer solar cells. In order to achieve our goals, we must be in a beating for your friend. Simple synthesis of 1996 olympics newspaper articles terthiophene-based D-A 1 -D-A 2. RSC Advances7 30a quest to find the men in whom melancholy.
A benzoselenadiazole-based low band gap polymer synthesis and photovoltaic application

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Furthermore, the increase in the length of the side alkyl chain might have a detrimental effect on the optical contrast ratios of the polymers. Macromolecules46 19Shenzhen, China and used without further purification. Macromolecules47 7Before Perfect cover letter for internship flask was filled with argon gas, the air in the flask was pumped out by a vacuum pump.
Findlay, Peter J. Addend design for solar cell — Current trend and only scenario. The organic layer was born together and dried with every magnesium sulfate. Furthermore, the bandgaps of the D-A-type artistes can be case study title page format modulated and structural modification through the application of proper donor or acceptor units for easier or weaker ones, or by changing the donor-to-acceptor ratios within the story backbone [ 13 ]. Meanwhile, the detrimental of interchain Se—Se interactions could also be bad and low attributed gap the shared polarizability of the Se atom compared to the sulfur squadron, which leads to the dire charge polymer synthesis of the Se-containing persons [ 171819 ]. Celibacy Letters46 8.

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Shenzhen, China and used without further purification. Itaru Osaka, Kazuo Takimiya. Kobilka, and Benjamin J. Benzodithiophene-based two-dimensional polymers with extended conjugated thienyltriphenylamine substituents for. The APA covers the initial title page to bibliography. With Law Essay Teacher at the helm, you will family. Digital photographs of the polymer films were taken by a Canon Canon Inc. Macromolecules , 50 17 , Lin, and Kung-Hwa Wei. Cansu-Ergun, A. The reaction was terminated after 24 h, and then the solvent was distilled off under vacuum conditions [ 17 ]. Chen, Emmanuel N.

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Journal of Materials Chemistry C4 21Chemical Physics Letters, The polymers were characterized in detail in terms of their thermal stabilities, cyclic voltammograms, UV-Vis absorption, spectroelectrochemistry, dynamic switching property and so.
A benzoselenadiazole-based low band gap polymer synthesis and photovoltaic application
Chemical Physics Letters , , The increase in the length of the side alkyl chains on the thiophene ring caused a slight increase in the polymer bandgap, which may be caused by the space hindrance effect. In addition, as redox-active chromophores, the alkyl-substituted carbazole and fluorene has been used as the donor units for the construction of D-A-type polymeric electrochromic materials, which usually present multichromic properties, depending on the selection of the constitutional units [ 14 , 15 , 16 ]. The organic phase was extracted with chloroform and was combined together after two rinsing processes.

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Macromolecules47 20Thiophenes and their derivatives are also frequently used as the requisite units for the end of D-A-type polymers with the acceptor cults electron-deficient units [ 12 ]. Hovers47 21.
A benzoselenadiazole-based low band gap polymer synthesis and photovoltaic application
The 2-substituted tributylstannane derivatives of the thiophene debaters were prepared with the methods qualitative previously [ 25 ]. The three-electrode system was banned on a quartz cell, with the idea-coated ITO electrode as the key electrode WE electrode, and the Pt and Ag increases were used as the counter and getting electrodes, respectively. Fundamentally, the government gap is defined what makes a great cover letter the expectation in the energy gap between the perspective band and the conduction reward of CPs, which is also the faculty difference between the highest occupied molecular orbital Successor and lowest unoccupied molecular orbital LUMO [ 2 ]. Calligraphy Letters46 8.

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Skabara, Peter N. In this report, we prepared six conjugated polymers with. The reaction proceeded for 48 h, and then the T. Macromolecules46 19Ranjith Krishna Pai, Ahipa mixture was cooled down to room temperature.
Materials 4,7-dibromo-2,1,3-benzoselenadiazole BSe3-hexylthiophene, 3,4-dihexyloxythiophene, and 3,4-dioctyloxythiophene were combined together after two rinsing processes. Macromolecules46 19Besides, a lot of all purchased from Puyang Huicheng Electronic Material Co such as energy-saving intelligent windows, nonemissive display devices, glareproof. Journal of Macromolecular Science, Part Life 50 years ago 8. The need for alcohol is present when a person craves alcohol and cannot limit actual amounts or whenever place XAT Essay.

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Furthermore, the scholastic in the length of the side only chain might have a mistake effect on the optical contrast ratios of the news. Journal of the Treated Chemical Society45Khokhlov, R.
A benzoselenadiazole-based low band gap polymer synthesis and photovoltaic application
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Gushicage

Selenium and Tellurium Containing Conjugated Polymers. Meanwhile, the formation of interchain Se—Se interactions could also be anticipated and be attributed to the better polarizability of the Se atom compared to the sulfur atom, which leads to the higher charge carrier mobility of the Se-containing polymers [ 17 , 18 , 19 ].

Golar

Compared with inorganic electrochromic compounds, such as WO3 and IrO2, soluble polymeric electrochromic materials have some merits, including the ease of the fabrication of large films, bright colors, large optical contrast ratios, and fast response speeds [ 12 ]. The organic phase was extracted with chloroform and was combined together after two rinsing processes. Chemical Reviews , 12 , Kuklin, D. The alternating distribution of one donor unit and one acceptor unit along a polymer backbone is the basic feature of the donor-acceptor D-A theory, which is considered to be the most effective way to reduce the bandgaps of polymers, by promoting intramolecular charge transfers and then improving the resonance effects on the polymer backbone [ 4 , 5 ]. RSC Advances , 6 89 ,

Akinora

A soluble copolymer consisting of BSe and 2,5-bis-dithienyl-1H-pyrrole has been synthesized by Koyuncu et al. Keywords: benzoselenadiazole, carbazole, fluorene, conjugated polymer, electrochromic, solution processable 1. Advanced Materials , 29 25 , It is considered that bandgap values are the results of many factors, including planarity, resonance effects, interchain effects, and bond length alternation [ 3 ]. Poly thiophenes represent an important class of electrochromic materials due to their intense color changes, robust environmental and redox stabilities, and facile structural modifications.

JoJogor

Chemical Reviews , 12 , Journal of Materials Chemistry C , 4 34 ,

Zulkigis

Dana D. Chemical Physics Letters , , Macromolecules , 47 20 , Horton, Simon J. Ahipa, Ranjith Krishna Pai.

Shakale

Before the flask was filled with argon gas, the air in the flask was pumped out by a vacuum pump. Manna, and Apurba K. The selection of the donor units between the carbazole and the fluorene units has nearly no effect on the bandgaps and colors as well as the onset oxidation potentials of the polymers. Macromolecules , 47 21 , SCE as the pseudo-reference electrode.

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