Ultrahigh electron-deficient pyrrolo-acenaphtho-pyridazine-dione based donor–acceptor conjugated polymers for electrochromic applications

Literature Information

Publication Date 2015-09-02
DOI 10.1039/C5PY01129A
Impact Factor 5.582
Authors

Qun Ye, Tingting Lin, Xuehong Lu


View Original

Abstract

Novel electron acceptors 2-alkyl-6,9-di(thiophen-2-yl)-1H-pyridazino[4′,5′:2,3]indeno[6,7,1-def]isoquinoline-1,3(2H)-dione and 2-alkyl-6,9-di(furan-2-yl)-1H-pyridazino[4′,5′:2,3]indeno[6,7,1-def]isoquinoline-1,3(2H)-dione derived from pyrrolo-acenaphtho-pyridazine-diones (PAPD) with a very low-lying lowest unoccupied molecular orbital (LUMO) level have been synthesized via a regioselective inverse electron demand Diels–Alder reaction between thiophene- and furan-substituted 1,2,4,5-tetrazine and an electron-deficient compound 2-(2-alkyl)-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione. The chemical structures of two PAPD monomers were confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry as well as single-crystal X-ray structural analysis. The time-dependent density functional theory (TD-DFT) calculations were performed to show that PAPD series monomers have a LUMO energy level down to −3.42 eV, much lower than the popular electron acceptors such as benzotriazole, benzothiadiazole and its fluorinated derivatives (−2.19–−2.98 eV). The PAPD based monomer was incorporated into a series of donor–acceptor type conjugated polymers comprising 3,3-bis((dodecyloxy)methyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine and thieno[3,2-b]thiophene as co-monomers through Stille coupling polymerization to give electrochromic conjugated polymers P1–P5 with high number-average molecular weights in the range of 42 000–67 000 (g mol−1). The polymers showed optical bandgaps between 1.90–1.99 eV. Electrochromic devices displayed reversible color changes between purple/red in the neutral state and greyish blue/grey in the oxidized state with an outstanding redox stability of less than 1% decrease in contrast after 800 cycles using polymer P3 as an example, and high optical contrasts of up to 80% at 1500 nm in the near infrared region.

Related Literature

The degradation mechanism of methyl orange under photo-catalysis of TiO2

Lihong Yu, Jingyu Xi, Ming-De Li, Hung Tat Chan, Tao Su, David Lee Phillips, Wai Kin Chan

2012-01-05 Paper

DOI: 10.1039/C2CP23226J

Insights from impedance spectroscopy into the mechanism of thermal decomposition of M(NH2BH3), M = H, Li, Na, Li0.5Na0.5, hydrogen stores‡

Karol J. Fijalkowski, Rafał Jurczakowski, Wiktor Koźmiński

2012-03-20 Paper

DOI: 10.1039/C2CP23344D

Interfaces of ionic liquids

2012-03-02 Editorial

DOI: 10.1039/C2CP90031A

Traveling interface modulations in the NH3 + O2 reaction on a Rh(110) surface

M. Rafti, H. Uecker, F. Lovis, V. Krupennikova, R. Imbihl

2012-02-15 Paper

DOI: 10.1039/C2CP23970A

Back cover

Cover

DOI: 10.1039/C2CP90052A

Spatial heterogeneity in a lyotropic liquid crystal with hexagonal phase

David P. Penaloza, Jr., Koichiro Hori, Atsuomi Shundo

2012-02-28 Communication

DOI: 10.1039/C2CP40284J

Hydrated-ion ordering in electrical double layers

Tanja Drobek, Tobias Balmer

2012-03-22 Paper

DOI: 10.1039/C2CP40255F

Superparamagnetic blocking and superspin-glass freezing in ultra small δ-(Fe0.67Mn0.33)OOH particles

G. Ennas, A. Scano, E. Agostinelli, D. Fiorani

2012-01-27 Paper

DOI: 10.1039/C2CP22473A

You might also like

Compound Q&A

What is 3-Fluoro-2-methylbenzylamine (CAS: 771573-36-5)?

3-Fluoro-2-methylbenzylamine is an organic compound with the CAS number 771573-3...

771573-36-53-Fluoro-2-methylben...
Compound Q&A

Is Tert-butyl 2-(oxetan-3-ylidene)acetate (CAS: 1207175-03-8) safe?

Tert-butyl 2-(oxetan-3-ylidene)acetate is considered safe for its intended uses ...

1207175-03-8Tert-butyl 2-(oxetan...
Compound Q&A

What precautions should be taken when handling 4-Acetyl-2-fluorobenzonitrile (CAS: 214760-18-6)?

Proper personal protective equipment (PPE) such as gloves, goggles, and a lab co...

214760-18-64-Acetyl-2-fluoroben...
Compound Q&A

How is 2-Ethyl-4-methyl-1,3-thiazole (CAS: 15679-12-6) typically synthesized?

2-Ethyl-4-methyl-1,3-thiazole is commonly synthesized via the reaction of thiour...

15679-12-62-Ethyl-4-methyl-1,3...
Compound Q&A

How should 5',5''-([2,2'-Bithiophene]-5,5'-diyl)bis(([1,1':3',1''-terphenyl]-4,4''-dicarboxylic acid)) (CAS: 1227780-71-3) be stored?

This compound should be stored in a cool, dry place away from direct sunlight an...

1227780-71-35',5''''-([2,2'-Bith...
Compound Q&A

What regulatory guidelines apply to L-Lysine Acetate Salt (CAS: 52315-92-1)?

L-Lysine Acetate Salt (CAS: 52315-92-1) is subject to various regulatory guideli...

52315-92-1L-LYSINE ACETATE SAL...
Compound Q&A

Is 6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) safe?

6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) is generally conside...

259793-96-96-Fluoro-3-hydroxy-2...
Compound Q&A

What are the physical and chemical properties of 1,1'-Sulfonylbis(1H-imidazole) (CAS: 7189-69-7)?

1,1'-Sulfonylbis(1H-imidazole) is a crystalline solid with a molecular weight of...

7189-69-71,1'-Sulfonylbis(1H-...
Compound Q&A

What industries use 4-methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5)?

4-Methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5) is primarily used i...

289483-82-54-methyl-7-nitro-1H-...
Compound Q&A

How should waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) be handled?

Waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) should be ...

97753-82-75-Bromo-3-indolyl-be...

Source Journal

Polymer Chemistry

Polymer Chemistry
CiteScore: 8.6
Self-citation Rate: 7.3%
Articles per Year: 457

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.