1308671-90-0Relevant academic research and scientific papers
Spiro linkage as an alternative strategy for promising nonfullerene acceptors in organic solar cells
Wu, Xiao-Feng,Fu, Wei-Fei,Xu, Zheng,Shi, Minmin,Liu, Feng,Chen, Hong-Zheng,Wan, Jun-Hua,Russell, Thomas P.
, p. 5954 - 5966 (2015)
This work focuses on developing diketopyrrolopyrrole (DPP)-based small molecular nonfullerene acceptors for bulk heterojunction (BHJ) organic solar cells. The materials, SF-DPPs, have an X-shaped geometry arising from four DPP units attached to a spirobifluorene (SF) center. The spiro-dimer of DPP-fluorene-DPP is highly twisted, which suppresses strong intermolecular aggregation. Branched 2-ethylhexyl (EH), linear n-octyl (C8), and n-dodecyl (C12) alkyl sides are chosen as substituents to functionalize the N,N-positions of the DPP moiety to tune molecular interactions. SF-DPPEH, the best candidate in SF-DPPs family, when blended with poly(3-hexylthiophene) (P3HT) showed a moderate crystallinity and gives a Jsc of 6.96 mA cm-2, Voc of 1.10 V, a fill factor of 47.5%, and a power conversion efficiency of 3.63%. However, SF-DPPC8 and SF-DPPC12 exhibit lower crystallinity in their BHJ blends, which is responsible for their reduced Jsc. Coupling DPP units with SF using an acetylene bridge yields SF-A-DPP molecules. Such a small modification leads to drastically different morphological features and far inferior device performance. These observations demonstrate a solid structure-property relationship by topology control and material design. This work offers a new molecular design approach to develop efficient small molecule nonfullerene acceptors. A series of spiro-diketopyrrolopyrroles-based nonfullerene acceptors with X-shapes is developed. The substituted alkyl side chains on the acceptors can significantly tailor their crystallinity and bulk heterojunction film morphology. When paring these acceptors with poly(3-hexylthiophene), a dramatic variation of power conversion efficiency from 1.42% to 3.63% is observed.
Solution-processed ambipolar field-effect transistor based on diketopyrrolopyrrole functionalized with benzothiadiazole
Zhang, Yuan,Kim, Chunki,Lin, Jason,Nguyen, Thuc-Quyen
, p. 97 - 105 (2012)
Ambipolar charge transport in a solution-processed small molecule 4,7-bis{2-[2,5-bis(2-ethylhexyl)-3-(5-hexyl-2,2′:5′, 2″-terthiophene-5″-yl)-pyrrolo[3,4-c]pyrrolo-1,4-dione-6-yl] -thiophene-5-yl}-2,1,3-benzothiadiazole (BTDPP2) transistor has been investigated and shows a balanced field-effect mobility of electrons and holes of up to ～10-2 cm2 V-1 s-1. Using low-work-function top electrodes such as Ba, the electron injection barrier is largely reduced. The observed ambipolar transport can be enhanced over one order of magnitude compared to devices using Al or Au electrodes. The field-effect mobility increases upon thermal annealing at 150°C due to the formation of large crystalline domains, as shown by atomic force microscopy and X-ray diffraction. Organic inverter circuits based on BTDPP2 ambipolar transistors display a gain of over 25. Copyright
Synthesis, characterization and photovoltaic properties of two-dimensional conjugated polybenzodithiophene derivatives appending diketopyrrolopyrrole units as side chain
Chen, Jianhua,Xiao, Manjun,Su, Wenyan,Duan, Xiongwei,Duan, Linrui,Peng, Wenhong,Tan, Hua,Yang, Renqiang,Zhu, Weiguo
, p. 4857 - 4864 (2014)
Two side-chain donor-acceptor (D-A) narrow-band-gap two-dimensional (2D) conjugated polymers of POBDTDPPs and PTBDTDPPs with benzodithiophene (BDT) as D unit and appending diketopyrrolopyrrole (DPP) as A unit were designed and synthesized. The optical, thermal, electrochemical and photovoltaic properties have been investigated. It was found that both polymers exhibit better solution processability and a deeper HOMO energy level relative to its corresponding main-chain conjugated polymers (PBDT-DPP). Moreover, the PTBDTDPPs with an additional di(alkylthiophene)- substituted BDT unit shows a deeper HOMO energy level than the POBDTDPPs with a dialkoxy- substituted BDT unit. Using PTBDTDPPs as an electron donor and [6,6]-phenyl-C71-butyric acid methyl ester as an electron acceptor, the resulting polymer solar cells (PSCs) exhibited meliorative photovoltaic properties with a power conversion efficiency (PCE) of 2.92% and open circuit voltage (Voc) of 0.94 V. The PCE and Voc levels are 1.52-2.92 and 1.14-1.18 times higher than those in the PBDT-DPP- and POBDTDPPs-based PSCs, respectively. This work demonstrates a good example for tuning energy level and photovoltaic properties of the polymers by the application of 2D conjugated structure.
Solution-processable diketopyrrolopyrrole derivatives as organic semiconductors for organic thin-film transistors
Kim, Hyekyoung,Van, Nguyen Pham Thanh,Kim, Choongik,Seo, SungYong
, p. 705 - 712 (2018)
Solution-processable diketopyrrolopyrrole derivatives having acetylene, 2,5-bis(2-ethylhexyl)-3-(5- (phenylethynyl)thiophen-2-yl)-6-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (3), 2,5-bis (2-ethylhexyl)-3-(thiophen-2-yl)-6-(5-(thiophen-2-ylethynyl)thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c] pyrrole-1,4-dione (4), and 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl)) bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (5) were synthesized and characterized as organic semiconductors for organic thin-film transistors (OTFTs). For the fabrication of thin films based on solution processable compounds, drop-casting (DC) and solution-shearing (SS) were employed. Thin films of compound 5 exhibited p-channel characteristics with carrier mobility as high as 5.7×10-4 cm2/Vs and a current on/off ratio of 104-106 for top-contact/bottom-gate OTFT devices.
Influence of Backbone Chlorination on the Electronic Properties of Diketopyrrolopyrrole (DPP)-Based Dimers
Xue, Ning,Wei, Yuan,Zhang, Guowei,Liu, Lele,Zhang, Lei
, p. 1050 - 1058 (2019)
Chlorination of π-conjugated backbones is garnering great interest because of fine-tuning electronic properties of conjugated materials for organic devices. Herein we report a synthesis of thiophene-based diketopyrrolopyrrole (DPP) dimers and their chlorinated counterparts by introducing a chlorine atom in the outer thiophene ring to investigate the influence of the chlorination on charge transport. The backbone chlorination lowers both the HOMO and the LUMO of the dimers and leads to a blue-shift of maximum absorption in compared to unsubstituted counterparts. X-ray analysis reveals that the chlorine atom prompts the outer thiophene ring out of the planarity of the backbone with a relatively large torsional angle. The chlorinated dimers exhibit slipped one-dimensional packing decorated with multiple intermolecular interactions, because of a combination of a negative inductive effect and a positive mesomeric effect of the halogen atom, which might facilitate charge transport within the oligomeric backbones. The mobility in the single-crystal OFET devices of the chlorinated dimers is up to 1.5 cm2 V?1 s?1, which is two times higher than that of the non-chlorinated DPP dimers. Our results indicate that the chlorine atom plays a key role in directing non-covalent interactions to lock the slipped stacks, enabling electronic coupling between adjacent molecules for efficient charge transport. In addition, our results also demonstrate that these DPP dimers with straight n-octyl chains exhibit higher mobilities than the dimers with branched 2-ethylhexyl chains.
A naphthodithiophene-diketopyrrolopyrrole donor molecule for efficient solution-processed solar cells
Loser, Stephen,Bruns, Carson J.,Miyauchi, Hiroyuki,Ortiz, Rocio Ponce,Facchetti, Antonio,Stupp, Samuel I.,Marks, Tobin J.
, p. 8142 - 8145 (2011)
We report the synthesis, characterization, and first implementation of a naphtho[2,3-b:6,7-b′]dithiophene (NDT)-based donor molecule in highly efficient organic photovoltaics (OPVs). When NDT(TDPP)2 (TDPP = thiophene-capped diketopyrrolopyrrole) is combined with the electron acceptor PC61BM, a power conversion efficiency (PCE) of 4.06 ± 0.06% is achieved - a record for a PC61BM-based small-molecule OPV. The substantial PCE is attributed to the broad, high oscillator strength visible absorption, the ordered molecular packing, and an exceptional hole mobility of NDT(TDPP)2.
Tri-diketopyrrolopyrrole molecular donor materials for high-performance solution-processed bulk heterojunction solar cells
Liu, Jianhua,Sun, Yanming,Moonsin, Preecha,Kuik, Martijn,Proctor, Christopher M.,Lin, Jason,Hsu, Ben B.,Promarak, Vinich,Heeger, Alan J.,Nguyen, Thuc-Quyen
, p. 5898 - 5903 (2013)
Two new high-performance DPP-containing donor molecules employing a molecular architecture with three DPP chromorphores (tri-DPP) in conjugated backbones are synthesized and characterized. The two tri-DPP molecules with only a structural difference on alk
Mono-/Bimetallic Neutral Iridium(III) Complexes Bearing Diketopyrrolopyrrole-Substituted N-Heterocyclic Carbene Ligands: Synthesis and Photophysics
Hobbie, Erik K.,Kilina, Svetlana V.,Lystrom, Levi,Pan, Yanxiong,Sun, Wenfang,Sun, Xinyang,Thomas, Salim A.,Wang, Hua,Xu, Wan,Yang, Zhongyu
, p. 15278 - 15290 (2021/10/20)
The synthesis and photophysics (UV-vis absorption, emission, and transient absorption) of four neutral heteroleptic cyclometalated iridium(III) complexes (Ir-1-Ir-4) incorporating thiophene/selenophene-diketopyrrolopyrrole (DPP)-substituted N-heterocyclic carbene (NHC) ancillary ligands are reported. The effects of thiophene versus selenophene substitution on DPP and bis- versus monoiridium(III) complexation on the photophysics of these complexes were systematically investigated via spectroscopic techniques and density functional theory calculations. All complexes exhibited strong vibronically resolved absorption in the regions of 500-700 nm and fluorescence at 600-770 nm, and both are predominantly originated from the DPP-NHC ligand. Complexation induced a pronounced red shift of this low-energy absorption band and the fluorescence band with respect to their corresponding ligands due to the improved planarity and extended π-conjugation in the DPP-NHC ligand. Replacing the thiophene units by selenophenes and/or biscomplexation led to the red-shifted absorption and fluorescence spectra, accompanied by the reduced fluorescence lifetime and quantum yield and enhanced population of the triplet excited states, as reflected by the stronger triplet excited-state absorption and singlet oxygen generation.
ORGANIC DYES, COMPOSITIONS AND DYE-SENSITIZED SOLAR CELLS
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Paragraph 0123; 0130-0131, (2021/01/29)
The present invention relates to a liquid crystal display device. The present invention relates to an organic dye, a composition including the same, and a dye-sensitized solar cell twisted π-spacer and DPP-based core unit introduced therein, and to a composition and a dye-sensitized solar cell including the same.
Synthesis of novel 3,6-dithienyl diketopyrrolopyrrole dyes by direct C-H arylation
Almenningen, David Moe,Gautun, Odd Reidar,Hoff, B?rd Helge,Venkatraman, Vishwesh,Yemene, Amsalu Efrem
, (2020/05/29)
Direct C-H arylation coupling is potentially a more economical and sustainable process than conventional cross-coupling. However, this method has found limited application in the synthesis of organic dyes for dye-sensitized solar cells. Although direct C-H arylation is not an universal solution to any cross-coupling reactions, it efficiently complements conventional sp2-sp2 bond formation and can provide shorter and more efficient routes to diketopyrrolopyrrole dyes. Here, we have applied palladium catalyzed direct C-H arylation in the synthesis of five new 3,6-dithienyl diketopyrrolopyrrole dyes. All prepared sensitizers display broad absorption from 350 nm up to 800 nm with high molar extinction coefficients. The dye-sensitized solar cells based on these dyes exhibit a power conversion efficiency in the range of 2.9 to 3.4%.
