Synthesis and properties of polythiophene derivatives containing triphenylamine moiety and their photovoltaic applications

Li, Yaowen; Xue, Lili; Xia, Haijian; Xu, Bin; Wen, Shizhu; Tian, Wenjing

doi:10.1002/pola.22737

Cited by 91 publications

(57 citation statements)

References 44 publications

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“…Such interchain linking increased the degree of twisting of the polymer backbone, thereby decreasing the effective conjugation length and, accordingly, increasing the value of E ox onset . 55 We observed higher values of E ox onset for CTM6C41 and CTM6C21 relative to those of TM6C41-OH and TM6C21-OH, presumably because of the higher degree of bridging through DMBPI units for CTM6C41 and CTM6C21. In addition, the decrease in the HOMO energy level upon increasing the degree of bridge linking correlated with the increase in the value of E ox onset .…”

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 72%

“…The decrease in the HOMO energy level upon increasing the OH group content corresponds with the increased value of E ox onset . 55 Moreover, the HOMO energy levels of the 6-hydroxyhexylfunctionalized copolymers were lower than those of the 2-hydroxyethyl-functionalized copolymers. On the other hand, the optical band gap of each copolymer, determined from the absorption edge, was approximately 2.3 eV.…”

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

“…In addition, the decrease in the HOMO energy level upon increasing the degree of bridge linking correlated with the increase in the value of E ox onset . 55 Because the optical band gap did not vary significantly with respect to the degree of bridge linking of the copolymers, the interchain-linked copolymers possessed lower LUMO energy levels relative to those of the corresponding OHcontaining side-chain copolymers.…”

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

“…The cyclic voltammograms of TM2C41-OH, TM2C21-OH, TM6C41-OH and TM6C21-OH revealed oxidation onset potentials (E ox onset ) at 0.80, 0.85, 0.83 and 0.87 V, respectively; that is, the value of E ox onset increased upon increasing the content of OH groups in the copolymers, presumably because they induced an increased degree of twisting of the polymer backbone, out of planarity. 55 Such twisting of the polymer backbone decreased the effective conjugation length, thereby enhancing the value of E ox onset . 55 In addition, the values of E ox onset for the 6-hydroxyhexyl-functionalized copolymers were higher than those of the 2-hydroxyethyl-functionalized copolymers.…”

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

“…55 Such twisting of the polymer backbone decreased the effective conjugation length, thereby enhancing the value of E ox onset . 55 In addition, the values of E ox onset for the 6-hydroxyhexyl-functionalized copolymers were higher than those of the 2-hydroxyethyl-functionalized copolymers. This observation implies that the presence of 6-hydroxyhexyl groups twisted the polymer backbone more significantly than did the presence of 2-hydroxyethyl groups.…”

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

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Synthesis and photovoltaic properties of a series of bulk heterojunction solar cells based on interchain-linked conjugated polymers

Lee

Chen

Shiau

2012

Polym J

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We have used Suzuki coupling to synthesize a series of maleimide-thiophene copolymers presenting pendent 2-hydroxyethyl and 6-hydroxyhexyl units. The maleimide-thiophene copolymers containing different contents of OH groups were then reacted with 3,3 0 -dimethoxy-4,4 0 -biphenylene diisocyanate (DMBPI) in solution to form the interchain-linked polymers. The interchainlinked polymers exhibited excellent solubility in organic solvents. The average molecular weight and thermal stability of the copolymers increased after interchain linking with DMBPI. The wavelengths of maximum absorption of the interchain-linked copolymers were red-shifted relative to those of the corresponding side-chain copolymers. The energy level of the lowest unoccupied molecular orbitals and highest occupied molecular orbitals decreased after the copolymers had undergone interchain linking with DMBPI. We fabricated polymer solar cells (PSCs) from blends of the interchain-linked copolymers and Keywords: fullerene derivative; maleimide-thiophene copolymer; polymer solar cell INTRODUCTIONThe development of novel low-band gap p-conjugated polymers is an attractive research area because bulk heterojunction polymer solar cells (PSCs) incorporating them can be fabricated at low cost with large areas, flexible shapes, light weight and solution processability. [1][2][3][4][5][6] The photoactive layer in most bulk heterojunction cells is based on a blend of an electron-donor conjugated polymer and an electronacceptor fullerene derivative, typically [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM). Several recent efforts have focused on the synthesis of a new low-band gap conjugated polymers that improve the absorption of solar radiation and increase charge mobilities. [7][8][9][10][11][12][13][14][15][16][17][18][19][20] In addition to the intrinsic characteristics of the polymer, the amount of PCBM in the blend, 17,18 the compatibility of the polymer and PCBM, the morphology of the photoactive layer 19-21 and the deviceprocessing conditions all have important roles affecting the photovoltaic (PV) performance of PSCs. [8][9][10]22,23 Photo-energy conversion efficiencies (Z) of 47% have been achieved for PSCs based on blends of poly(thiophene) derivatives and fullerene derivatives. [7][8][9][10]24,25 In addition to the short-circuit current densities (J SC ) and values of Z that are typically measured, recent investigations have also been made into optimizing the PV efficiency stability of PSCs. For example, incorporation of a ultraviolet (UV) shielding layer into a PSC can

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Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 72%

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

Section: Electrochemical Properties Of the Maleimide-thiophene Copolymentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and photovoltaic properties of a series of bulk heterojunction solar cells based on interchain-linked conjugated polymers

Lee

Chen

Shiau

2012

Polym J

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The Synthesis of Conjugated Polythiophenes by K umada Cross‐Coupling

Koch

Heeney

2012

Materials Science and Technology

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Conjugated polymers have been the subject of intensive research efforts over the past few decades. Much of this interest has stemmed from the fact that such materials combine the inherent processibility and mechanical robustness associated with polymers, with the electronic properties more typically associated with inorganic semiconductors. Thus, such materials may allow the fabrication of electronic devices on a variety of flexible or conformable surfaces, by a range of potentially low-cost and large-area deposition techniques such as printing. Possible applications include field effect transistors for display backplanes, organic solar cells, electrochromic displays, chemical sensors, and polymeric light-emitting diodes [1].Within the realms of conjugated polymer research, thiophene-containing materials have been one of the most widely investigated classes for many of the above applications [2,3]. Thiophene is a cheap and widely available electron-rich, planar aromatic heterocycle which is readily functionalized by range of chemistries. As a result, it can be copolymerized with a variety of aromatic comonomers to generate polymers with extended π-electron delocalization along the backbone. The alternating double and single bonds of the delocalized conjugated system are nondegenerate, leading to an energy band gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). For many of the optoelectronic applications outlined above, the absolute energy levels of the HOMO and LUMO, as well as the band gap between them, are important parameters affecting device performance. As such, major research efforts have been devoted to understanding how chemical structure can influence the electronic delocalization of conjugated polymers. Whilst these factors are complex, they can be related to points such as the attachment of electron-donating/-withdrawing substituents to the polymer backbone, the degree of backbone planarity (and, therefore, the π-electron overlap and delocalization), and the nature and aromaticity of any comonomers included in the polymer backbone.

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New Conjugated Polymers and Synthetic Methods

McNeil

Lanni

2012

Materials Science and Technology

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The sections in this article are Introduction New Polymers Prepared via Chain‐Growth Methods End‐Functionalized Polymers All‐Conjugated Block Copolymers Mechanism Initial Observations and Mechanistic Proposal Subsequent Mechanistic Studies End‐Group Analysis Rate and Spectroscopic Studies Indirect Support for an Intermediate Ni(0)‐Polymer π‐Complex Remaining Limitations Conclusions and Outlook

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Synthesis and properties of polythiophene derivatives containing triphenylamine moiety and their photovoltaic applications

Cited by 91 publications

References 44 publications

Synthesis and photovoltaic properties of a series of bulk heterojunction solar cells based on interchain-linked conjugated polymers

Synthesis and photovoltaic properties of a series of bulk heterojunction solar cells based on interchain-linked conjugated polymers

The Synthesis of Conjugated Polythiophenes by K umada Cross‐Coupling

New Conjugated Polymers and Synthetic Methods

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