566939-58-0Relevant articles and documents
Synthesis and photovoltaic properties of thieno[3,4-c]pyrrole-4,6-dione- based donor-acceptor Copolymers
Wen, Shanpeng,Cheng, Weidong,Li, Pengfei,Yao, Shiyu,Xu, Bin,Li, Hui,Gao, Yajun,Wang, Zilong,Tian, Wenjing
, p. 3758 - 3766 (2012)
Three donor-acceptor (D-A) 1,3-di(thien-2-yl)thieno [3,4-c]pyrrole-4,6- dione-based copolymers, poly{9,9-dioctylfluorene-2,7-diyl-alt-1,3-bis(4- hexylthien-2-yl)-5-octylthieno[3,4-c]pyrrole-4,6-dione}, poly{N-(1-octylnonyl) carbazole-2,7-diyl-alt-1,3-bis(4-hexylthien-2-yl)-5-octylthieno[3,4-c]pyrrole-4, 6-dione}, and poly {4,8-bis(2-ethylhexyloxyl) benzo[1,2-b:3,4-b']dithiophene- alt-1,3-bis(4-hexylthien-2-yl)-5-octylthieno[3,4-c] pyrrole-4,6-dione} were synthesized by Suzuki or Stille coupling reaction. By changing the donor segment, the bandgaps and energy levels of these copolymers could be finely tuned. Cyclic voltammetric study shows that the highest occupied molecular orbital (HOMO) energy levels of the three copolymers are deep-lying, which implies that these copolymers have good stability in the air and the relatively low HOMO energy level assures a higher open-circuit potential when they are used in photovoltaic cells. Bulk-heterojunction photovoltaic cells were fabricated with these polymers as the donors and PC71BM as the acceptor. The cells based on the three copolymers exhibited power conversion efficiencies of 0.22, 0.74, and 3.11% with large open-circuit potential of 1.01, 0.99, and 0.90 V under one sun of AM 1.5 solar simulator illumination (100 mW/cm2).
Design, synthesis and electronic properties of push-pull-push type dye
Kundu, Rajen,Kulshreshtha, Chandramouli
, p. 77460 - 77468 (2015)
A Sonogashira cross-coupling protocol was employed for the construction of a push-pull-push type dye. An ethynyl π-spacer extends the effective π-conjugation length between push and pull units without altering the planarity of the electron donor/acceptor pair. The variation of the strength of the alkyne π-spacer electron push (or donor) units of these dyes has a strong effect on the shifting of both absorption and emission maxima and thereby on the Stokes shift. The dyes were solvatochromic and their solvatochromicity was highly dependent on the electron push unit. Strong red shifted emissions were likely to arise due to the internal charge transfer (ICT) from the electron push unit to the electron pull unit. Calculated energy values of HOMO → LUMO transitions are in good accordance with experimental observations. Alkyne conjugated electron push units (-CC-Ar; Ar = Ph, Ph-OMe, Ph-NMe2) are more effective to increase the EHOMO levels. Overall, experimental and theoretical results of the push-pull-push dyes indicate that they can be used as promising conjugated materials with predictable electronic properties for optoelectronic devices.
A thieno[3,4- c ]pyrrole-4,6-dione-based copolymer for efficient solar cells
Zou, Yingping,Najari, Ahmed,Berrouard, Philippe,Beaupre, Serge,Reda Aich, Badrou,Tao, Ye,Leclerc, Mario
, p. 5330 - 5331 (2010)
A new low-band-gap thieno[3,4-c]pyrrole-4,6-dione-based copolymer, PBDTTPD, has been designed and synthesized. PBDTTPD is soluble in chloroform or o-dichlorobenzene upon heating and shows a broad absorption in the visible region. The HOMO and LUMO energy levels were estimated to be at ?5.56 and ?3.75 eV, respectively. These electrochemical measurements fit well with an optical bandgap of 1.8 eV. When blended with PC71BM, this polymer demonstrated a power conversion efficiency of 5.5% in a bulk-heterojunction photovoltaic device having an active area of 1.0 cm2.
Thieno[3,4-c]pyrrole-4,6-dione-based small molecules for highly efficient solution-processed organic solar cells
Ha, Jong-Jin,Kim, Yu Jin,Park, Jong-Gwang,An, Tae Kyu,Kwon, Soon-Ki,Park, Chan Eon,Kim, Yun-Hi
, p. 1045 - 1053 (2014)
Two small molecules named BT-TPD and TBDT-TTPD with a thieno[3,4-c]pyrrole- 4,6-dione (TPD) unit were designed and synthesized for solution-processed bulk-heterojunction solar cells. Their thermal, electrochemical, optical, charge-transport, and photovoltaic characteristics were investigated. These compounds exhibit strong absorption at 460-560nm and low highest occupied molecular orbital levels (-5.36eV). Field-effect hole mobilities of these compounds are 1.7-7.7×10-3cm2V-1s -1. Small-molecule organic solar cells based on blends of these donor molecules and a acceptor display power conversion efficiencies as high as 4.62 under the illumination of AM 1.5G, 100mWcm-2. Powering up: Two small molecules named BT-TPD and TBDT-TTPD with a thieno[3,4-c]pyrrole-4,6-dione (TPD) unit are designed and synthesized for solution-processed bulk-heterojunction solar cells. Small-molecule organic solar cells based on blends of these donor molecules and a phenyl-C61-butyric acid methyl ester acceptor display power conversion efficiencies (η) as high as 4.62.
The rational design of a redox-active mixed ion/electron conductor as a multi-functional binder for lithium-ion batteries
Hwang, Chihyun,Lee, Jungho,Jeong, Jihong,Lee, Eunryeol,Kim, Jonghak,Kim, Seoyoung,Yang, Changduk,Song, Hyun-Kon
supporting information, p. 4751 - 4757 (2021/03/09)
A redox-active mixed ion and electron conductor (redox-active MIEC) is presented as a binder for the lithium titanate anodes of lithium-ion batteries. The redox-active MIEC binder (symbolized by PT*-GmCn) was designed to be (1) electrically conductive along its conjugated thiophene backbone (PT = polythiophene), (2) redox-active from its succinimide moiety (* = redox-active) and (3) ionically conductive by adopting glyme (G) branches. It was superior to the practically used PVdF binder in terms of lithium ion diffusivity and electrical conductivity (1.4× and 15?000×, respectively). High capacity was guaranteed, particularly at high rates due to its MIEC nature of PT*-GmCn, while an additional capacity was achieved from its redox activity.
Controlling the optoelectronic properties of narrow bandgap organic chromophores upon isoelectronic bridgehead substitution
Hwan Wang, Dong,Kwon, Obum,Park, Jin Kuen,Park, Soyun
, p. 233 - 239 (2018/10/15)
Two types of narrow bandgap organic molecules were synthesized by changing two bridgehead atoms to examine the effect on the optoelectronic properties. Notably, it was found that the bridgehead atoms mostly affected their crystallinity and that the intermolecular forces and their optoelectronic properties were controllable upon manipulating the forces by processing additives.
Poly(5-alkyl-thieno[3,4-: C] pyrrole-4,6-dione): A study of π-conjugated redox polymers as anode materials in lithium-ion batteries
Robitaille, Amélie,Perea, Alexis,Bélanger, Daniel,Leclerc, Mario
supporting information, p. 18088 - 18094 (2017/09/08)
Organic polymers have been investigated as active electrode materials in the past few years and although materials with high energy density and tunable redox potential have been developed, their dissolution into the electrolyte and their low electronic conductivity compromised their use in rechargeable batteries. To overcome these drawbacks, seven n-type π-conjugated redox polymers based on 5-alkyl-thieno[3,4-c]pyrrole-4,6-dione have been developed for anode materials of rechargeable batteries. The role of the carbonyl group on the electrochemical activity of these polymers has been demonstrated and the effect of the alkyl chain and the comonomer unit on their electrochemical performance. The redox potential of the polymer has been shown to vary over a range of 400 mV and a polymer with a suitable redox potential of 1.55 V vs. Li/Li+ for an anode of a lithium-ion battery has been found.
Direct Imide Formation from Thiophene Dicarboxylic Acids Gives Expanded Side-Chain Selection in Thienopyrrolediones
Wolfe, Rylan M. W.,Reynolds, John R.
supporting information, p. 996 - 999 (2017/03/15)
The synthesis of thienopyrroledione (TPD) has been updated to reduce the number of synthetic steps, remove hazardous and toxic reagents, reduce the amount of byproduct waste, and reduce the use of solvents when unnecessary. Diverse functionalization is possible, introducing 16 examples in yields from 34% to 95%. This reaction scheme was shown to be general for thiophene imides, and a more thorough exploration into side chain engineering is presented with TPD acceptors often used in organic electronic applications.
THIENO, FURO AND SELENOPHENO-[3,4-C]PYRROLE-4,6-DIONE COPOLYMERS
-
Paragraph 00111, (2014/03/25)
Novel photoactive copolymers based on thieno, furo or selenopheno-[3,4- c]pyrrole-4,6-dione-derivative are described herein. More specifically, the photoactive copolymers comprise repeating units of Formula I -[A1-A2]- I wherein A1 is an electron donating unit such as a mono or polycyclic heteroaryl that is unsubstitued or substituted with one or more C1-20-alkyl or C1-20-alkoxy; and A2 is an alkylfuro or alkylselenopheno-[3,4-c]pyrrole-4,6-dione-derivative. The photoactive copolymers are suitable for use in BHJ solar cells.
Fine tuning of frontier orbital energy levels in dithieno[3,2-b:2′, 3′-d]silole-based copolymers based on the substituent effect of phenyl pendants
Ikai, Tomoyuki,Kudo, Tomoya,Nagaki, Masahiro,Yamamoto, Tomoyuki,Maeda, Katsuhiro,Kanoh, Shigeyoshi
, p. 2139 - 2145 (2014/05/06)
A series of dithieno[3,2-b:2′,3′-d]silole-based π-conjugated copolymers containing thieno[3,4-c]pyrrole-4,6-dione or thieno[3,4-b]thiophene units bearing 4-substituted phenyl pendants were synthesized and their thermal stability, optical properties and frontier orbital energy levels were systematically investigated. The introduction of electron-withdrawing substituents on the phenyl rings lowered their frontier orbital energy levels without deteriorating their thermal and optical properties. By replacing an electron-donating methoxy group with an electron-withdrawing trifluoromethyl group, both the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital energy levels of the polymers were deepened by more than 0.3 eV. A relatively linear relationship was observed between the HOMO energy levels and the Hammett substituent constants.
